100 Holiday Classics – Billboard

Our staff’s picks for our 100 favorite songs to soundtrack the Christmas season.

Michelle Rohn

There’s a reason that listeners seem to get more impatient every year for the Christmas music season to start: Nothing else feels quite like it. The things that make Christmas songs great — whether carols, old pop standards or newer enduring hits — are most of the same things that make pop great in general: emotional connection, universal relatability, unshakeable catchiness.

People have been singing about Christmas almost as long as it’s been celebrated. And with each passing year, more than a few contemporary artists try their hand at crafting a new seasonal standard, something sweet and melancholy that lingers in the pine-scented air for as long as it takes you to finish a candy cane (without chewing, that is). Some succeed, as with these modern Christmas classics; others, which just dropped this year, have yet to prove their mistletoe mettle. But when they do connect, it’s magic – not to mention a holly jolly payday.

Christmas music has a wavelength entirely its own, shared by an overwhelming majority of its most recognizable classics: a sublime yearning that’s at once profoundly saddening and deeply comforting. It evokes a visceral, nearly oppressive sentimentality, one fortified and strengthened by a lifetime’s worth of associated holiday memories — personal, familial, romantic, nostalgic. It’s music for the most wonderful time of the year, even if it always makes you cry.

And it never goes away. Well, maybe for 10 months of the year, it goes into hibernation — but you know it’ll be back next November at the latest, and it’ll include the same songs it has for your entire life. Unlike the oldies and classic rock canons, which are forced to update their timeline parameters every so often (or at least shed some old songs to make room for the new), being a Christmas standard is a lifetime appointment. Perennials that date back the better part of a century at this point are still ubiquitous every holiday season, while new seasonal releases often take whole decades to prove their worthiness. It makes every Christmas season a musical family gathering where everyone shows up and co-exists peacefully — something precious few of us are lucky enough to be able to say about our actual families’ real-life holiday celebrations.

Here are Billboard‘s staff picks for the 100 greatest Christmas songs of all time — songs that, try as folks might, no amount of commercial overplay or corporate co-opting can seem to ruin.

Trans-Siberian Orchestra, “Christmas Eve/Sarajevo 12/24” (1996)

Image Credit: Courtesy Photo

Holiday 100 Chart Peak: No. 4 (Dec. 2012)

Why It’s a Gift: In a genre largely devoid of prog rock, the biggest hit from Trans-Siberian Orchestra (who, surprise, hails from Tampa!) is a Christmas jam for everyone who’s more into headbanging than holly. Amalgamating elements of “God Rest Ye Merry Gentlemen” and “Carol of the Bells,” then blowing them up to arena-sized proportions with crashing drums and truly bitchin’ guitar, this one barrels through our speakers like a freight train of cheer every holiday season, and we’re always down to get onboard.

Schmaltz Factor (rated on a scale of 1 to 10): 10, straight up. “Christmas Eve/Sarajevo 12/24” is totally over the top in a way that’s totally unique to the holiday season. — KATIE BAIN
Louis Armstrong and the Commanders, “Zat You, Santa Claus?” (1953)

Holiday 100 Peak: N/A

Why It’s a Gift: This swinging jazz number‘s creeping baritone sax bassline recalls the score of a cheesy ‘30s horror movie, while the lyrics evoke Abbott & Costello Meet Frankenstein – “Cold winds are howling, or could that be growling?” — but the brassy instrumental breaks are as bright as a Staten Island Christmas display. (Ask Pete Davidson.) The song has been covered umpteen times since Armstrong’s original, but it’s Satchmo’s gravel road of a voice that makes his version the alpha and the omega.

Schmaltz Factor: 3. The song gives in to a Hollywood ending. It is Santa, not Oogie Boogie outside the door. Until then though, it’s a kicky shot of navy strength rum in the gloppy eggnog punch bowl of Christmas hits. — FRANK DIGIACOMO
Smino feat. Monte Booker and Masego, “Sleigh” (2019)

Holiday 100 Peak: N/A

Why It’s a Gift: Appearing on his overlooked holiday two-pack High 4 Da Highladays, Smino’s “Sleigh” is a cozy track that finds the singer-rapper fully embracing his neo-soul sound. With help from frequent collaborator/producer Monte Booker and singer-saxophonist Masego, the trio create a vibe perfect for an adult Christmas Eve party full of drinking, card games — and of course, getting high for the holidays.

Schmaltz Factor: 1. As unique as Smino is as an artist, he created an equally original holiday song(s) while staying true to his soulful artistry and sound. And for “Sleigh” to make this list only being two years old, he obviously did something right. — CYDNEY LEE
Johnny Mathis, “The Sounds of Christmas” (1963)

Holiday 100 Peak: N/A

Why It’s a Gift: Considering Johnny Mathis’ run of Christmas albums coincided with the rise of rock on radio in the ’60s, his fealty to traditional vocal stylings put him on the outs with the ‘cool crowd’ of the Boomer generation. A pity, since his buttery vibrato is every bit as warm and heartening as a hot toddy after a long trek through a blizzard, which could not be clearer than on this immaculately packaged confection.

Schmaltz Factor: It’s a 10, but that’s no knock on “The Sounds of Christmas.” In 1963, the then-closeted Mathis, like any good friend of Dorothy, could deftly deliver delicious kitsch without ever delving into false histrionics. — JOE LYNCH
La Rondallita, “El Burrito Sabanero” (1972)

Holiday 100 Peak: N/A

Why It’s a Gift: “El Burrito Sabanero” has been covered by many artists, including Juanes and Aloe Blacc, but it’s the original 1972 release by children’s musical group La Rondallita that endures, almost 50 years later. A simple yet rhythmic Venezuelan folk song has become a timeless staple across Latin American countries and injects nostalgia every holiday season.

Schmaltz Factor: 9. In addition to being a children’s tune, “Burrito” has a religious background, telling the story about the pilgrimage of the shepherds to meet at the birth of the child Jesus. That’s not the cheesy part though — it’s the galloping beat and the ever-famous “tuki tuki tuki” for us. — JESSICA ROIZ

Britney Spears, “My Only Wish (This Year)” (2000)

Holiday 100 Peak: No. 81 (Jan. 2015)

Why It’s a Gift: At the absolute height of Britney Spears’s cultural dominance in 2000, she decided to spread some holiday cheer (via melancholic lyrics) with this Christmas banger. From the cheesy lyrics about having Santa deliver a lover for the holiday to her iconic vocal runs and fries throughout the song, Britney put in the work to make sure that Santa heard her wish.

Schmaltz Factor: 9. Even for an early-2000s pop track, this song is absolutely dripping with the sugar-soaked, overly-sentimental lyrics that made Spears a star. Opening the song’s lyrics up with a sad walk in the snow while watching other couples hold hands is a peak set-up for the hokey (yet still incredibly catchy) chorus. — STEPHEN DAW

!!!, “And Anyway It’s Christmas” (2013)

Holiday 100 Peak: N/A

Why It’s a Gift: Dance-punk outfit !!! (pronounced chk chk chk) melt the heart while heating up the dancefloor with the twinkling shimmy of this holiday romance rave-up. Cascading piano and bubbling bass set the sentimental glow for the song’s brief encounter, while frontman Nic Offer offers the swoon-worthiest moment on the opening verse: “I’ve been ’round the world, seen all kinds of girls/ But I’ve seen nothing better than you in that sweater.”

Schmaltz Factor: 5. “And Anyway It’s Christmas” is too limber to ever totally give way to schlock, but Offer leans into his crooniest impulses throughout, and it’s hard to call any song whose second verse ends with a dramatically whispered “Merry Christmas” schmaltz-free. — ANDREW UNTERBERGER

Dan Fogelberg, “Same Old Lang Syne” (1980)

Holiday 100 Peak: No. 97 (Dec. 2013)

Why It’s a Gift: Fogelberg’s melancholy ballad describes a chance encounter by former lovers. Drawn from a real-life experience Fogelberg had in the mid-’70s, “Same Old Lang Syne” tells its story with honesty, insight and empathy; like the best songs by Fogelberg’s contemporary Harry Chapin, it’s really a movie in a five-minute pop song. The writers of those glossy Christmas movies on the Hallmark Channel should listen to this for inspiration.

Schmaltz Factor: 3. It’s an emotional song, no two ways about that, but it steps over the line into schmaltz just once, near the end, with the line, “And as I turned to make my way back home, the snow turned into rain.” But then Michael Brecker’s soprano sax solo closes the track on a graceful note. – PAUL GREIN

Destiny’s Child, “Carol of the Bells” (a.k.a. “Opera of the Bells”) (2001)

Holiday 100 Peak: N/A

Why It’s a Gift: “Carol of the Bells” has long been known as a traditional, old school Christmas carol, but Destiny’s Child’s take feels modern without sacrificing its festive magic by checking off everything on our wish list to Santa – soaring harmonies, Beyoncé’s unmatched runs, and spirited vocals from all three members that make it hard to believe that the song is performed a cappella. I mean, who needs instruments when you’re Destiny’s Child?

Schmaltz Factor: 3, and that’s only because of the stereotypically merry lyrics – “Christmas is here / Bringing good cheer / To young and old / Meek and the bold.” Destiny’s Child significantly tones down the schmaltziness by tastefully opting for a rich vocal performance instead of the usual jingle bells and festive instrumentals. — RANIA ANIFTOS

Pansy Division, “Homo Christmas” (1992)

Holiday 100 Peak: N/A

Why It’s a Gift: Queercore punk vets Pansy Division’s alt holiday gem is undoubtedly the most sexually explicit song on our list, but it’s also one of the funniest and one of the sweetest — a gleeful and truly merry celebration of getting what you really want most for Christmas, even if it’s a gift that rhymes with sock.

Schmaltz Factor: 3. In its own way, “Homo Christmas” is as corny as it is horny, but ultimately it’s only as schmaltzy as a song that prominently features the rectal insertion of candy canes can really be. — A.U.

The Flaming Lips, “A Change at Christmas (Say It Isn’t So)” (2003)

Holiday 100 Peak: N/A

Why It’s a Gift: Although the C-word appears in the title, this track from the Lips’ Ego Tripping at the Gates of Hell EP is not your typical holly jolly horses–t. It’s a melancholy meditation — with a heady bass drum kick — about how the world “embraces peace and love and mercy instead of power and fear” at Christmas. “But then,” frontman Wayne Coyne laments, “it passes along with the season” and “we just go back to the way we were.”

Schmaltz Factor: 2. Despite all the glockenspiel-and-sleigh bell-accented realism, “A Change at Christmas” evokes hope instead of pathos. “I think it’s all going to work out just fine,” says Coyne at song’s end. And for that one shining musical moment, you want to believe him. — F.D.

Mecano, “Un Año Más” (1988)

Holiday 100 Peak: N/A

Why It’s a Gift: Legendary Spanish pop trio Mecano (made up of Ana Torroja and siblings José María and Nacho Cano) included “Un Año Más (One More Year) in their 1988 album Descanso Dominical, which wasn’t a holiday album. The set would become the top-selling album in Spain that year, and the nostalgic synth-pop third single “Un año” reprised every year since as a New Year’s celebration staple that’s been covered by dozens of artists in varying formats and languages.

Schmaltz Factor: 7. “Un año más” is a laundry list of every New Year’s celebration customary in Spain. Compounded by a message of togetherness (“Among shouts and whistles, Spaniards big and small do something together, for once”), it could come off as cringe-worthy — save for a dreamy, gorgeous melody that saves it from triteness. — LEILA COBO

Tom Petty and the Heartbreakers, “Christmas All Over Again” (1992)

Holiday 100 Peak: N/A

Why It’s a Gift: Classic rock cachet. When Jimmy Iovine asked Tom Petty to record something for his 1992 A Very Special Christmas Vol. 2 compilation, Petty trekked to his native Florida with a ukulele gifted to him by George Harrison and with it wrote “Christmas All Over Again,” in an attempt to emulate the larger-than-life sound of 1963’s A Christmas Gift for You from Phil Spector (“That was the only one we could relate to,” Petty said in the liner notes for 1995’s Playback) — and he succeeded wildly.

Schmaltz Factor: 3. If you dropped the bells and changed the lyrics, this would just be a really solid Tom Petty and The Heartbreakers song. — K.B.

Willie Nelson, “Pretty Paper” (1964)

Holiday 100 Peak: N/A

Why It’s a Gift: To a sweet country box-step rhythm, Nelson sings the holiday tale of a street vendor calling out to Christmas shoppers “hoping you won’t pass him by” as he offers “pretty paper, pretty ribbons of blue” to “wrap your presents to your darling from you.” Before Nelson recorded the song, Roy Orbison’s version reached No. 15 on the Billboard Hot 100 in 1963. Covers followed, from Glen Campbell to Dolly Parton, while Kenny Chesney’s version (featuring Nelson) went to No. 45 on Hot Country Songs in 2004.

Schmaltz Factor: 4. The backstory of the song was revealed in a 2008 Nelson biography in which author Joe Nick Patoski wrote that Nelson was inspired by a disabled man, who could not walk, but sold paper and pencils outside a department store in Fort Worth, Texas. — THOM DUFFY

Kate Bush, “December Will Be Magic Again” (1980)

Holiday 100 Peak: N/A

Why It’s a Gift: Kate Bush is the gift here. With “December Will Be Magic Again,” she takes the traditional concept of a holiday record and makes it her own — the tingling, opening piano chords and her limitless vocal range break right through those conventions with a magical force that only Kate Bush can conjure.

Schmaltz Factor: 3.Its gentle hints of holiday atmosphere give it some schmaltz, but it’s a Kate Bush record above all else. — E.J. PANALIGAN

Fats Domino, “I’ll Be Home For Christmas” (1993)

Holiday 100 Peak: N/A

Why It’s a Gift: Bing’s original from 1943 was a WWII era hit for overseas troops, but this 1993 rendition from an AARP-eligible Fats Domino gives the oft-covered classic an amiable New Orleans flavor. Countless singers can rock out a Christmas classic; few but Fats knew how to imbue an endlessly covered tune with that distinct roll on the ivories.

Schmaltz Factor: Unlike most versions, this is a 3 on the schmaltz scale. Given the lyrical content of this one, singers tend to ham up its homesickness. Not Fats: The rock n’ roll architect makes this standard feel like a long-lost friend whose warm, easy personality makes you wonder why you ever lost touch in the first place. — J. Lynch

Alexander O’Neal, “Our First Christmas” (1988)

Holiday 100 Peak: N/A

Why It’s a Gift: “Our First Christmas” hails from an Alexander O’Neal album literally titled My Gift to You — and when it’s delivered care of peak Jimmy Jam and Terry Lewis, who produced the whole LP and penned the set’s five originals, it’s certainly worth a thank you note. The song’s chorus crackles like a hearth, with incandescent synths and harmonies wrapped around O’Neal’s hearty delivery of the central question: “It’s our first Christmas/ Will you still love me on New Year’s Eve?”

Schmaltz Factor: 7. The bumping late-’80s production keeps it from being suffocating, but lyrics like “I caught you in the toy department/ We met under the mistletoe” are much better heard in O’Neal’s robust belting than read on paper. — A.U.

Dean Martin & Marilyn Maxwell, “Baby It’s Cold Outside” (1949)

Holiday 100 Peak: No. 17 (Dec. 2018)

Why It’s a Gift: While the jury’s still out on whether this winter classic is flirty or creepy (man trying to coerce woman into sleeping over after a date?), “Baby, It’s Cold Outside” remains a sing-along staple around the holidays. Dean Martin’s billowing vocals gently overlapping with Marilyn Maxwell’s delicate tone make for a cozy-by-the-fire feel, as described in the 77-year-old song written by Frank Loesser.

Schmaltz Factor: 4. Considering there’s no actual mention of Christmas or any holiday, combined with the track’s originality as a wintertime duet, this cut ranks relatively low in the schmaltz department. — NEENA ROUHANI

DeJ Loaf feat. Kodak Black, “All I Want For Christmas” (2016)

Holiday 100 Peak: N/A

Why It’s a Gift: If you’re going to release a holiday song keyed around the phrase “All I really want for Christmas is you,” better make sure it has a vibe entirely of its own. Luckily, rapper DeJ Loaf’s “All I Want For Christmas” accomplishes that fairly effortlessly, with a down-home sentimentality that focuses on a familial” you” rather than a romantic one — climaxing with a nostalgic spoken-word outro reflecting on how Christmas spirit is more about who you’re celebrating with than which new sneakers are waiting for you under the tree. “You can’t take those type of things for granted,” she allows; too true.

Schmaltz Factor: 5. The tender keys and jingling bells lay it on pretty thick, but DeJ Loaf’s delivery sounds so matter-of-fact — and feels so hard-earned — that the song never veers into mawkish territory. — A.U.

Kacey Musgraves, “Christmas Makes Me Cry” (2016)

Holiday 100 Peak: N/A

Why It’s a Gift: With the holiday exerting such a powerful emotional pull in all directions, even the most chipper of Christmas enthusiasts rarely can make it through the whole season without finding themselves in at least one maudlin moment. It’s a reality evocatively recognized by Kacey Musgraves’ downbeat “Christmas Always Makes Me Cry,” which finds the country star trying to get in the spirit but perennially pulling up short. “It seems like everybody else is having fun,” she frets, slumped on the shoulder of plucked acoustics and moaning strings. “I wonder if I’m the only one….” Yeah, don’t worry about that one too much, Kacey.

Schmaltz Factor: Maybe a 6 — the song and production unquestionably go straight for the heartstrings, but Kacey’s delivery eschews high melodrama for the gentle frustration of Charlie Brown getting the Christmas football pulled out from him yet again. — A.U.

Tony Bennett, “Winter Wonderland” (1968)

Holiday 100 Peak: No. 87 (Dec. 2017)

Why It’s a Gift: Since the song’s creation in the ‘30s, artists spanning countless genres have tried their hand at “Winter Wonderland” — including Selena Gomez, Blake Shelton and even Snoop Dogg in recent years. Still, it’s Bennett’s jazzy rendition that captures the song best more than five decades later. It’s airy enough to create the sensation of a pleasant stroll, and saves its brightest moments until the very end to make all the surrounding scenery sparkle.

Schmaltz Factor: 5. The legendary singer mostly keeps it snappy as listeners frolic through winter-themed bliss, but don’t be mistaken: Bennett takes advantage of moments, both small (expanding “fire” into “fi-yah-ah-ahhh”) and large (the song’s rousing conclusion), to remind people that he knows how to work a crowd. — JOSH GLICKSMAN

Carla Morrison, “Jesús” (2016)

Holiday 100 Peak: N/A

Why It’s a Gift: Carla Morrison’s Navidad anthem “Jesús” is a gauzy indie rock ballad off her 2016 EP La Niña del Tambor. A solemn oath to remember and honor the birth of Jesus, the poignant lyrics also serve as a moment of reflection: “Today is Christmas and although it seems like any other day, you came to remind me that you gave everything up for my dreams, that I should love everyone equally and celebrate that we’re a part of you.”

Schmaltz Factor: 5. If anything, “Jesús” is an ultra-sentimental song that serves as a reminder of the real meaning of Christmas. “This day is special because today you were born, to become flesh and bones, to embrace us and love us,” Morrison emotionally sings. — GRISELDA FLORES

Dolly Parton, “Hard Candy Christmas” (1982)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 97 (Jan. 2015)

Why It’s a Gift: Originally featured in the musical The Best Little Whorehouse in Texas (and the subsequent 1982 film, starring Parton as the madam), it may be the only Christmas song set in a brothel. The wistful ballad, poignantly rendered by Parton, is more about rising above one’s circumstances and desired new beginnings than the holidays, especially when all Santa has in his bag is a few pieces of hard candy.

Schmaltz Factor: 4  There’s a little melodrama to be sure, but when Parton sings “I’m barely getting through tomorrow, but still I won’t let sorrow bring me way down,” it’s like an angel’s blessing promising a brighter day is coming. — MELINDA NEWMAN

The Ronettes, “Sleigh Ride” (1963)

Holiday 100 Peak: No. 9 (Dec. 2020)

Why It’s a Gift: This version of the holiday standard “Sleigh Ride” has it all: a horse neighing, jingle bells, the clip-clopping of hooves. But all the cutesy bells and whistles have nothing on Ronnie Spector’s casually cool delivery and her Ronettes’ ring-a-ling-a-ling-a-ding-dong-ding backing vocals. Our cheeks are nice and rosy thanks to the song’s warm Wall of Sound production and sped-up tempo — that horse is really moving!

Schmaltz Factor: 3. This song can be so cheesy, but The Ronettes somehow make it cool. – KATIE ATKINSON

Perry Como, “(There’s No Place Like) Home For the Holidays” (1954)

Holiday 100 Peak: No. 13 (Dec. 2018)

Why It’s a Gift: This is a fine example of American pop music in the decade between the end of World II and the arrival of rock and roll. Its relative blandness while exhorting the superiority of spending the Christmas season at the homestead is part of its charm.

Schmaltz Factor: 8. It’s pure Americana, from the line about “homemade pumpkin pie” to the recurring lines about motoring cross-country to spend time with loved ones. You want to call that schmaltz? OK, but “when you pine for the sunshine of a friendly gaze,” this tune will be waiting for you. — P.G.

Sufjan Stevens, “That Was the Worst Christmas Ever!” (2006)

Image Credit: Courtesy Photo

Holiday 100 Peak: N/A

Why It’s a Gift: In the middle of Sufjan Stevens’ 2006 five-disc box set Songs For Christmas is an understated folk gem that wraps Stevens’ songwriting strengths during the Illinois era — harmonized refrains, graceful myth-making, Christian undertones, banjo — in holiday-friendly packaging.

Schmaltz Factor: 2. Sure, there are warm recollections of snow-shoveling and sled-riding, but that bit about the father “throwing gifts in the wood stove” helps explain the song title here. — JASON LIPSHUTZ

Hector Lavoe y Willie Colón, “Aires de Navidad” (1970)

Holiday 100 Peak: N/A

Why It’s a Gift: As if a collaboration between salsa icons Hector Lavoe and Willie Colón isn’t gift enough on its own, this ’70s classic brings a tropical Christmas to any household. In Puerto Rico, especially, it marks the beginning of the island’s nearly three-month-long holiday season.

Schmaltz Factor: 5. A salsa song that takes you on a journey through a Puerto Rican Christmas, especially an asalto navideño, which is how the barrios celebrate, “Aires de Navidad” has just the right amount of sentimental value. — J.R.

Simon & Garfunkel, “7 O’Clock News/Silent Night” (1966)

Holiday 100 Peak: N/A

Why It’s a Gift: “7 O Clock News / Silent Night” is more of a political art piece than a holiday charmer, but that is why it remains one of the most powerful renditions of “Silent Night” to date. In juxtaposing the soft savior ballad with a raucous retelling of the 7 O Clock News — complete with racism, war, and murder — it acts as an apt reflection of American life in 1966. And while it was made prior to today’s 24/7 news cycle, it foreshadowed the ever-presence of Bad News and the plight we all face, trying to find peace despite it all.

Schmaltz Factor: 1. “7 O Clock News / Silent Night” is one surefire way to sober up after too many spiked egg nogs. — KRISTIN ROBINSON

Nat King Cole, “O Come All Ye Faithful” (1960)

Holiday 100 Peak: No. 38 (Dec. 20)

Why It’s a Gift: Cole, a wildly talented jazz pianist with an implacable cool, was gifted with one of the richest, most distinctive voices of his era. Bing Crosby’s version from the ’40s of this 18th century Christmas carol (originally known as “Adeste Fideles”) was stately and genteel, but Nat sings it with a warmth and familiarity — even when he switches to Latin, no small feat — that makes this religious favorite resonate for all, even the less-than-faithful.

Schmaltz Factor: It’s an 8. Ralph Carmichael’s orchestral arrangement is alternately swelling and subdued; those backup singers, however, are exactly the kind of saccharine drip that rock would soon exile from radio. But with Cole‘s casual vocal precision in play, this 1960 recording of a centuries-old classic feels like a fitting tug-of-war between play-acting and authenticity. And what’s more Christmas than that? — J. Lynch

De La Soul, “Millie Pulled a Pistol on Santa” (1991)

Holiday 100 Peak: N/A

Why It’s a Gift: De La Soul’s brilliantly bleak tale of a young girl finally fighting back against the domestic abuse that no one around her (including the song’s narrating rappers) takes seriously isn’t an obvious holiday song, save for the titular confrontation taking place over Christmas. But it’s that holiday setting that makes the story unforgettable: So many seasonal classics focus on the importance and safety of being home for the holidays that framing Xmas as the backdrop for a traumatized Millie’s revenge makes it a particularly knuckles-out gut punch.

Schmaltz Factor: Even a 1 is probably too high for a song this gritty and chilling. — A.U.

Eagles, “Please Come Home For Christmas” (1978)

Holiday 100 Peak: No. 18 (Jan. 2013)

Why It’s a Gift: Originally released in 1960 by blues singer/pianist Charles Brown, the Eagles scored a top 20 Hot 100 hit with this most melancholy of Christmas tunes. Brown’s version is sad enough, but the Eagles even changed his lyrics from “bell’s will be ringing the glad, glad news” to “bells will be ringing the sad, sad news” for their 1978 take. If your holiday is a bummer, this song is a reminder that the poor sap in the song has it worse… every single year.

Schmaltz Factor: 2. While soulful isn’t always a word associated with the Eagles, Don Henley pours it on here as he pleads with his loved one to say they’ll be home for Christmas and he can be happy once again. It’s more heartbreaking than corny. — M. Newman

Marco Antonio Solís / Los Bukis, “Navidad Sin Ti” (1987)

Holiday 100 Peak: N/A

Why It’s a Gift: Most recently covered by emerging regional Mexican acts Fuerza Régida and Eslabon Armado, “Navidad Sin Ti” is a gift that keeps on giving and is played on loop during the holidays in Spanish radio stations. Penned by Marco Antonio Solís and originally released in the mid-’80s by his Los Bukis outfit, what makes his version so special is Solís’ melancholic interpretation, which gives you chills as he sings, “Christmas is here and I’m without you, in this solitude/ I remember the day I lost you and I don’t know where you are/ But really, for your happiness, I will cheer for that on this Christmas.”

Schmaltz Factor: 6. Here, Solís validates whoever is feeling alone on Christmas. It’s not all “Jingle Bells” and “Feliz Navidad” — sometimes you just want to be in your feelings on Christmas, and that’s OK too. — G.F.

Celine Dion, “O Holy Night” (1998)

Holiday 100 Peak: No. 44 (Dec. 2017)

Why It’s a Gift: This song dates back to the 1800s, but the pop rendition we’re familiar with today was ushered in by producer David Foster’s piano-forward arrangement for Michael Crawford in 1993 – and Foster returned to the song with Dion five years later to prove what an epic vocal showcase it can be. Dion gets the dynamics of the plaintive ballad just right: starting the song in barely a whisper and ending with her patented power note.

Schmaltz Factor: 4 — It’s a bombastically earnest performance. – K.A.

Bing Crosby & The Andrews Sisters, “Mele Kalikimaka (Merry Christmas)” (1950)

Holiday 100 Peak: No. 25 (Dec. 2020)

Why It’s a Gift: You need more than two hands to count the number of holiday standards that Bing Crosby has done definitive versions of, but on none of them does he sound like he’s having nearly as much fun as he does on this warm-weather (and perhaps somewhat appropriative) collab with the Andrews sisters, a jaunty instruction to folks on the mainland in “Hawaii’s way to say, ‘Merry Christmas to you.’” Maybe that’s why “Mele Kalikimaka” is the one where, despite its many covers, it’s still nearly impossible to imagine any other voice but Crosby’s bouncing along its title phrase.

Schmaltz Factor: 5. It’s still Bing, but it’s too sunny to be all that schmaltzy. — A.U.

Andy Williams, “Happy Holiday/The Holiday Season” (1963)

Holiday 100 Peak: No. 12 (Dec. 2019)

Why It’s a Gift: Williams introduced this spirited medley on The Andy Williams Christmas Album in 1963 — the same year his Days of Wine and Roses topped the Billboard 200 for a remarkable 16 weeks. Bing Crosby and Marjorie Reynolds sang Irving Berlin’s “Happy Holiday” in the 1942 film Holiday Inn. Kay Thompson wrote “The Holiday Season.” Marty Paich (father of Toto’s David Paich) arranged this spiffy coupling of the two songs.

Schmaltz Factor: 4. With the swinging tempo and Williams’ spry vocal, you barely notice some of the cornball lyrics, like, “Leave a peppermint stick for old St. Nick/ Hanging on the Christmas tree.” — P.G.

James Brown, “Santa Claus Go Straight to the Ghetto” (1968)

Image Credit: courtesy Photo

Holiday 100 Peak: N/A

Why It’s a Gift: With it’s signature JB horn stabs, urgent ad-libs and funky bass, Brown’s loving 1968 snapshot of what the holiday looks like in the inner city was a welcome relief from the traditionally lily-white strains of old school Christmas pop music.

Schmaltz Factor: 3 — Brown is not going for nostalgia or soft-focus memories with this R&B burner. Instead, he offers a funky plea to help those who don’t have from someone who knows how it feels to wake up to an empty space under the tree on Christmas morning. — GIL KAUFMAN

Stevie Wonder, “Someday at Christmas” (1966)

Holiday 100 Peak: No. 76 (Jan. 2016)

Why It’s a Gift: “Someday at Christmas” is a rare Christmas song that speaks about more than just the holiday. Released in 1966 – partially in response to the Vietnam War – the song calls for an end to global conflict and a world where every person is free, along with a gorgeous bassline and a joyous melody that makes it feel at home amongst Christmas classics.

Schmaltz Factor: 3. The song doesn’t rate high on the schmaltz factor since Wonder sings that he hopes all men are free, but “Maybe not in time for you and me.” But Wonder is still celebrating the holidays every year with his Toys For Tots concerts and let’s hope he sees peace “someday at Christmastime.” — TAYLOR MIMS

U2, “Christmas (Baby Please Come Home)” (1987)

Holiday 100 Peak: N/A

Why It’s a Gift: U2 took perhaps the highest degree-of-difficulty assignment with their choice of cover for 1987’s first all-star A Very Special Christmas compilation — and delivered like they’d been prepping their entire life for it. Bono in particular wrings every ounce of desperation possible from the song’s subtitular plea, saving a couple extra “BAAAAAABY PLEASE COME HOME!”s for a post-chorus that probably made even Darlene Love marvel at how bad he was down.

Schmaltz Factor: 8. Love’s original was dramatic without going over the top, but Bono is practically rabid with his scenery-chewing here. — A.U.

Vince Guaraldi Trio, “O Tannenbaum” (1965)

Holiday 100 Peak: No. 29 (Jan. 2019)

Why It’s a Gift: Vince Guaraldi’s jazzy take on “O Tannenbaum” sheds the somewhat formal nature of the classic Christmas carol with casual yet jolly piano runs that provide a warmth that feels like the holidays at home, cozied up by the fireplace. No wonder it’s a fan favorite from the A Charlie Brown Christmas Soundtrack – it’s innocent, intimate and heartwarming, just like the Peanuts holiday special itself.

Schmaltz Factor: 6. It’s unexpectedly sentimental, and its association with Charlie Brown, Snoopy, Linus and the rest of the bunch makes Guaraldi’s “O Tannenbaum” cozy, cute and at least slightly schmaltzy by default. — R.A.

Clarence Carter, “Back Door Santa” (1968)

Holiday 100 Peak: N/A

Why It’s a Gift: Christmas isn’t only for the good little girls and boys, and the perpetually funky Clarence Carter was happy to sneak in to give the Christmas pop canon its first classic entry that could be described as “raunchy.” By later Blowfly standards, the PG-13 nefariousness of “Back Door Santa” is still pretty tame, but its sexy (and sax-y) strut leaves little mystery about what it intends, and the song even puts the stankiest of its many double-entendres right in front as its title.

Schmaltz Factor: 1. Any schmaltz deployed by Clarence Carter is strictly for diversional purposes. — A.U.

Pandora, “Los Peces en el Rio” (1986)

Image Credit: Courtesy Photo

Holiday 100 Peak: N/A

Why It’s a Gift: Although Billboard can’t confirm the song’s origins, there’s no doubt that “Peces en el Rio” was made popular by ’80s music trio Pandora. Its edgy alternative beat turned this symbolic Christmas carol into a Xmas jam that all generations will forever enjoy.

Schmaltz Factor: 8. It’s not the song so much as how it features on the very nostalgic festive album Eterna Navidad, which includes Latin ‘90s pop stars (Mijares, Yuri, Daniela Romo & more) doing their own renditions of Christmas carols. Now if we were talking about the music video, this would be an easy 10! — J.R.

Whitney Houston, “Do You Hear What I Hear?” (1987)

Holiday 100 Peak: No. 35 (Dec. 2011)

Why It’s a Gift: “A voice as big as the sea,” you say? Then Whitney Houston is the right woman for the job. This performance — from 1987’s A Very Special Christmas charity compilation — is a showcase for what made Houston such a singular pop star, as she marries her church-choir upbringing with a top 40 sensibility to create a spiritual experience even for the non-believers.

Schmaltz Factor: 6. There’s a lot of over-the-top moments in these lyrics, but with Houston’s vocal delivery, it all works. — K.A.

Charles Brown / Johnny Moore’s Three Blazers, “Merry Christmas Baby” (1956)

Holiday 100 Peak: N/A

Why It’s a Gift: Recorded by Johnny Moore’s Three Blazers in 1947 and by Rock and Roll Hall of Famer Charles Brown in 1956 after he departed that group, this frisky blues ballad boasts an all-time great lyric (“I haven’t had a drink this morning / But I’m all lit up like a Christmas tree”) and has been covered by everyone from Chuck Berry to Bruce Springsteen — but never bested.

Schmaltz Factor: 2. In an era best-known for producing heartstring-tugging holiday ballads, the post-WWII “Merry Christmas Baby” is the slow, cool secular Christmas song the other half needed, a slice-of-life salute to “good music on my radio” and kisses “beneath the mistletoe” borne on a bluesy piano roll. — J. Lynch

The Chipmunks With David Seville, “The Chipmunk Song (Christmas Don’t Be Late)” (1958)

Holiday 100 Peak: N/A

Why It’s a Gift: Written by Ross Bagdasarian (a.k.a. Seville) for his high-pitched cartoon band Alvin and the Chipmunks, this amusing and still fairly tender Grammy-winning novelty was the first Christmas record to reach No. 1 on the Billboard Hot 100 — later making a No. 70 Hot 100 comeback in 2007, thanks to the animated group’s self-titled live action film — before Mariah Carey again claimed the holiday throne in 2019.

Schmaltz Factor: 8. While the Chipmunks and mischievous frontman Alvin were popular among baby boomers and their families in the late ‘50s and ‘60s, and Nickelodeon still airs a revamped offshoot of the band’s ‘80s cartoon series, “The Chipmunk Song” has lost some of its comedic charm against animated fare like Spidey and His Amazing Friend, Paw Patrol and popular recurrent A Charlie Brown Christmas. — GAIL MITCHELL

Michael Bublé, “It’s Beginning to Look a Lot Like Christmas” (2011)

Holiday 100 Peak: No. 10 (Dec. 2012)

Why It’s a Gift: “It’s Beginning to Look a Lot Like Christmas” had been a hit for Perry Como and The Fontane Sisters with Mitchell Ayres & His Orchestra as well as Johnny Mathis, but Bublé’s descending cadence while crooning “A pair of hop-a-long boots and a pistol that shoots” makes the 1951 classic trot to a gentler, satisfying pace.

Schmaltz Factor: 6. He doesn’t adhere to the other versions’ merry yet choppy verses and makes the sparkling percussive intro more subtle, but the Canadian singer sprinkles his signature swelling jazz sound all over his extended “It’s Beginning to Look a Lot Like Christmas” before his orchestral grand finale celebrates, “Sure it’s Christmas once more.” — HERAN MAMO

Prince, “Another Lonely Christmas” (1984)

Holiday 100 Peak: N/A

Why It’s a Gift: Prince was so unbeatable in 1984 that he could relegate a wholly original and heartbreaking holiday song to B-side status (“I Would Die 4 U” was the A-side) and no one blinked. It’s almost a shame, because his virtuoso performance and the song’s sly lyrics (“Remember the time we swam naked in your father’s pool? / Boy, he was upset that night, but boy, was that ever cool”) make it the rare Christmas recording that demands your attention every time.

Schmaltz Factor: 3. The setup and delivery of “Another Lonely Christmas” would be total schmaltz in the hands of most artists, but Prince was the rare artist who could make an over-the-top performance feel as genuine and serious as your last words to a lover. Which, come to think of it, is exactly what this is. — J. Lynch

The Muppets, “We Need a Little Christmas” (1987)

Image Credit: Courtesy Photo

Holiday 100 Peak: N/A

Why It’s a Gift: With all due respect to Dame Angela Lansbury, this peppy song from the 1966 Broadway musical Mame is best performed by Muppets. The road-trip sing-along – featured in 1987’s A Muppet Family Christmas – is the ideal vehicle for all the wassail wordplay (“haul out the holly,” “we need a little snappy, happy ever after”) in this impatient Christmas carol, as Fozzy Bear drives a truck packed with his fuzzy friends through the snow.

Schmaltz Factor: 5. It’s hand puppets singing a song from a Broadway musical, so there must be some schmaltz. – K.A.

The Jackson 5, “I Saw Mommy Kissing Santa Claus” (1970)

Holiday 100 Peak: No. 45 (Jan. 2012)

Why It’s a Gift: What makes this Motown version of a 1952 Christmas staple stand out among the rest is a 12-year-old Michael Jackson’s show-stopping pipes and adorable ad libs. In the soulful rendition, the youngest Jackson brother attempts to convince his brothers that he really did see mommy kissing Santa Claus, between big production and cheerful composition.

Schmaltz Factor: 8. The very things that make this song a gift are also what make it so cheesy. Despite it being MJ, the track is still sung by a 12-year-old, and combined with Jackson’s pleas (“Come on, fellas, believe me!”) and the classic Christmas sleigh bells, the track can incite a little bit of reflexive cringe. — N.R.

Taylor Swift, “Christmases When You Were Mine” (2007)

Holiday 100 Peak: N/A

Why It’s a Gift: Taylor Swift’s five-track Holiday Collection was 80% an inessential seasonal stopgap between her first two albums — but the lone exceptional track was an absolute knockout. With its underplayed acoustic lilt and teardrops-on-her-guitar-stained vocal, “Christmases When You Were Mine” carries with it a brutal ache and longing that the then-17-year-old Swift should’ve been a decade away from truly understanding, let alone being able to vocally translate in such heartbreaking fashion.

Schmaltz Factor: 4. The sentiment is heavy but never really cheesy, and you have to wonder if the fact that it sounds so unmistakably personal is the reason why no one’s really tried to cover it yet. — A.U.

The Drifters, “White Christmas” (1954)

Holiday 100 Peak: No. 30 (Jan. 2016)

Why It’s a Gift: Hard to imagine anyone had really been missing the swing in “White Christmas” until The Drifters showed up, swaying with their organ and hi hat groove and irresistible “dub-dub, dub-da-dub” backing vocals. But what really makes the song an essential version of the biggest Christmas pop standard ever is the contrast of Bill Pinkney’s lead bass vocal and Clyde McPhatter and the rest of the quartet’s higher harmonies when they come soaring in late in the verse, a masterful moment from one of the most storied groups in R&B history.

Schmaltz Factor: 5. Nobody’s totally de-schmaltzing “White Christmas,” but a cover this lithe and rubbery is about as close as you can get. — A.U.

Ramones, “Merry Christmas (I Don’t Want to Fight Tonight)” (1987)

Image Credit: Courtesy Photo

Holiday 100 Peak: N/A

Why It’s a Gift: Punks need to rock around the Christmas tree too, right? The famously battling “brudders” managed to keep it civil while paying homage to their favorite girl group sound on a surprisingly joyous ditty about sharing love and good cheer while avoiding the usual Christmas crack-ups.

Schmaltz Factor: 6 (10 if you’re a true punk) The idea of punk OG Joey Ramone writing a semi-sweet song of the season seems absurd at first. But the combo of the group’s signature buzz saw guitars, sleigh bells and Joey’s search for the holiday’s hallmarks (“Where is Santa and his sleigh?/ Tell me why is it always this way?/ Where is Rudolph, Where is Blitzen,baby?”) makes this an enduring cretin carol. — G.K.

Merle Haggard, “If We Make It Through December” (1973)

Holiday 100 Peak: N/A

Why It’s a Gift: This Haggard-penned song is a stark reminder that the holiday season doesn’t always mean presents piled high beneath a gilded tree. Here, a father was laid off from his factory job just before Christmas and can’t offer a bountiful harvest of gifts that year. He does his best to convince himself that better times are ahead if they can make it to Spring. The song was a four-week No. 1 on Billboard‘s Hot Country Songs chart, and while it has been covered by artists like Alan Jackson, the Pistol Annies and Phoebe Bridgers, it’s Haggard’s grim yet hopeful delivery that remains the benchmark.

Schmaltz Factor: 1. It would be easy for a song about surviving through a hard-scrabble holiday season to become melodramatic, but The Hag’s heart-weary vocal, paired with understated instrumentation, renders the song with a stoic dignity. — JESSICA NICHOLSON

The Temptations, “Silent Night” (1980)

Holiday 100 Peak: No. 27 (Jan. 2014)

Why It’s a Gift: Recorded by a Who’s Who of major artists since its 1818 inception, “Silent Night” got the Tempts’ traditional treatment in 1968, helmed by Eddie Kendricks’ heavenly falsetto — and then this more popular soulful interpretation captained by the soothing, sonorous voices of Dennis Edwards, Melvin Franklin and Glenn Leonard.

Schmaltz Factor: 2. Between its gospel undertones, ad-libbed verses like “If I had one wish in this world / It would be that all men would be free” and Franklin’s deep bass wishing everyone a heartfelt “Merry Christmas,” this 1980 “Silent Night” truly hits home 41 years later in the wake of the ongoing pandemic and social unrest. — G.M.

Kanye West feat. CyHi da Prynce & Teyana Taylor, “Christmas in Harlem” (2010)

Holiday 100 Peak: N/A

Why It’s a Gift: “Christmas in Harlem” is as wholesome a holiday posse cut as you’re going to get from this GOOD Music collective — Teyana Taylor’s angelic, reminiscent hook on the beauties of the holidays is paired with picture-painting verses and classic Kanye-isms: “My only question is, ‘Where my present?’/ She said, ‘Shhh,’ she got a gift for me that ain’t for the kids to see.”

Schmaltz Factor: 5. The “winter wonderland”-esque instrumental and Taylor’s lovely chorus lean heavily into the sentimentality of the holidays, but Kanye’s signature charisma and contributions from the rest of the song’s star-studded rap lineup reels it in and keeps things level. — E.J.P.

Los Tigres del Norte, “Navidad de los Pobres” (1993)

Holiday 100 Peak: N/A

Why It’s a Gift: Los Tigres del Norte are the voice of the pueblo, and they gifted the pueblo with this Christmas anthem, which translates to “Christmas of the poor.” “They said God comes down on Christmas Eve on a white star, to share with us, poor and rich,” the song says. “But he stays longer at the poor people’s table to take away our hardships.”

Schmaltz Factor: 7. Los Tigres del Norte never fail to deliver a poignant corrido, and this Christmas anthem is no exception: “That’s why, as a poor man, I feel fortunate when Christmas Eve comes because I know God is by my side.” — G.F.

Elton John, “Step Into Christmas” (1973)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 84 (Dec. 2017)

Why It’s a Gift: Elton John promises to help find a way to entertain listeners in the Christmas bop’s second verse and he does not let down. “Step Into Christmas” is meant to make its way into the holiday song rotation at that perfect point of celebratory bliss, when just enough eggnog has been consumed, torn wrapping paper litters the floor and no distant relatives have started talking politics.

Schmaltz Factor: 8. It doesn’t get much schmaltzier than Elton John asking the listener to “hop aboard the turntable.” The song is playful and a beautiful ode to end any year. — T.M.

Otis Redding, “Merry Christmas Baby” (1967)

Holiday 100 Peak: No. 43 (Jan. 2020)

Why It’s a Gift: With his gritty yet supple voice and powerful gospel-style delivery, Redding made bluesy downers like “Fa-Fa-Fa-Fa (Sad Song)” and “Mr. Pitiful” crowd pleasers. So, when he recorded this happy, romantic Christmas classic, it became — and remains — an effective means of growing grinchy hearts three sizes in two minutes and 36 seconds.

Schmaltz Factor: 2. If the song didn’t arrive freighted with the tragedy of Redding’s death in a December 1967 plane crash, his version of “Merry Christmas Baby” would be schmaltz-free. Charles Brown and Chuck Berry’s cooler, slinkier (and similar) renditions from 1947 and 1958, respectively, are classics in their own right, but Redding’s radiates the kind of warmth that defines the season. — F.D.

Frank Sinatra, “Have Yourself a Merry Little Christmas” (1957)

Holiday 100 Peak: No. 20 (Dec. 2015)

Why It’s a Gift: Sinatra’s velvety voice fills the room like a warm embrace throughout his rendition of the quaint holiday classic. He opens the first eight seconds of the song strictly on the power of his own singing, with backing instruments — and soon thereafter, a choir — slowly swelling to join him, but you’ll have felt your troubles begin to melt away long before then.

Schmaltz Factor: 3. He spruced up a lyric or two from the original to make it more jolly, but the song is a down-the-middle effort that speaks for itself. Sometimes, it’s better to skip all of the bells and whistles, even during Christmastime. — J.G.

The Ronettes, “Frosty the Snowman” (1963)

Holiday 100 Peak: No. 82 (Dec. 2017)

Why It’s a Gift: Gene Autry popularized this song in 1950, but The Ronettes gave it extra verve and attitude in 1963 when they recorded it for Phil Spector’s legendary holiday album, A Christmas Gift for You. That was the same year they teamed with Spector to record the immortal “Be My Baby,” a No. 2 hit on the Billboard Hot 100.

Schmaltz Factor: 2. Not much schmaltz here; Spector’s Wall of Sound had a vigor and tautness that wouldn’t allow for it. – P.G.

Carpenters, “Merry Christmas Darling” (1970)

Holiday 100 Peak: No. 24 (Dec. 2012)

Why It’s a Gift: Karen Carpenter, Karen Carpenter, Karen Carpenter. Her vocal on “Merry Christmas Darling” as she longs for her loved one, who is away for Christmas and New Year’s Day, is pure, sublime perfection. She conveys the perfect mix of yearning, sadness and hope since she knows, even though it’s unspoken, they will be joyfully reunited after the holidays. Over 50 years since its release, it’s still the soundtrack for any college couples separated during the holiday break.

Schmaltz Factor: 7. There’s nothing schmaltzy about Carpenter’s wistful vocals on this 1970 gem — it’s the background singers that bring on the cheese, as does the somewhat clunky line “the logs on the fire fill me with desire,” and turning “Christmasing” into a verb. But they just add to the song’s dreamy reverie. — M. Newman

The Kinks, “Father Christmas” (1977)

Image Credit: Courtesy Photo

Hot 100 Peak: N/A

Why It’s a Gift: One of Ray Davies’ most indelible sing-alongs, “Father Christmas” pairs the biting humor of a department store Santa getting mugged by a hard-luck gang with a loping hook — easy enough to hum along with, even if you’re oblivious of the class warfare at its core.

Schmaltz Factor: 3. Although “Father Christmas” is largely a social satire, its final verse re-centers its focus on those less fortunate around the holiday season in an affecting way: “Have yourself a merry, merry Christmas / Have yourself a good time / But remember the kids who got nothin’ / While you’re drinkin’ down your wine.” — J. Lipshutz

Ella Fitzgerald, “Let It Snow! Let It Snow! Let It Snow!” (1960)

Holiday 100 Peak: N/A

Why It’s a Gift: This do-your-worst dare to the gods of winter has proven a timeless holiday classic since it was first written by Sammy Cahn and Jule Styne in 1945 — even though, strictly speaking, nothing about it is particularly December-specific. Regardless, it’s Ella Fitzgerald’s brisk, jazzy 1960 version (from the appropriately titled Ella Wishes You a Swinging Christmas) that’s proven the very coziest, a quick glance outside that just confirms that everything is as it should be inside.

Schmaltz Factor: 4. “I’ve brought some corn for popping” is about as…. well, corny a holiday lyric as they come, but Fitzgerald paces her way through it (and the rest of the song) so quickly and delightfully that there’s simply no time to get bogged down in the thickness. — A.U.

El Gran Combo de Puerto Rico, “No Hay Cama Pa’Tanta Gente” (1988)

Holiday 100 Peak: N/A

Why It’s a Gift: Can we please just party? While many think Christmas in Latin American countries is all about pious activity, dancing and jubilation is a central component to the season. El Gran Combo’s song was meant to be a party with every salsa name that mattered in attendance, with name-dropping galore (Perez Prado, Celia Cruz, Ralph Mercado, Hector Lavoe, to name a few), and became the de facto celebration track for the revelers.

Schmaltz Factor: 1. Here, Christmas is just an excuse to hit the dance floor til the early hours of morning. — L.C.

Thurl Ravenscroft, “You’re a Mean One, Mr. Grinch” (1966)

Holiday 100 Peak: No. 14 (Jan. 2017)

Why It’s a Gift: In a world where Christmas songs are usually serious, religious, romantic or tear-inducingly sentimental, “You’re a Mean One, Mr. Grinch” is refreshingly funny. The three-minute roast fest of the Grinch lays on burn after relentless burn, bringing a strange sense of levity to the holiday season. “Your soul is an appalling dump heap overflowing with the most disgraceful assortment of rubbish imaginable?” It’s hilarious. Imagine saying that to someone.

Schmaltz Factor: 7, just because Ravenscroft is so over-the-top in listing the reasons why the Grinch sucks, with enough bullying to keep his furry green heart two sizes too small. — R.A.

Bing Crosby & David Bowie, “Peace on Earth/Little Drummer Boy” (1977)

Holiday 100 Peak: No. 87 (Jan. 2014)

Why It’s a Gift: Nearly 45 years later, there is still nothing normal about watching one of most successful mainstream entertainers of the ’30s to ’50s share a mic with the transcendently weird/wired Bowie. Somehow, though, the forced marriage on this string-laden, soft rock duet recorded for Crosby’s 1977 Merrie Olde Christmas special has become one of the most enduring, beloved holiday classics. The key is the way it pairs Crosby’s mellow croon with Bowie‘s high harmonies and counter-melodies as they meld the two old chestnuts into one beautifully weird, warm modern carol.

Schmaltz Factor: 9. If you count the super awkward two-minute “getting to know you talk-up” at the beginning of the song’s video, this duet has enough cheese in it to clog your arteries worse than a straight egg nog IV. But those voices? If you don’t get chills from hearing these two masters bounce back and forth, then you deserve that lump of coal. — G.K.

The Jackson 5, “Santa Claus Is Coming to Town” (1970)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 24 (Dec. 2020)

Why It’s a Gift: Thanks to an arrangement that is equal parts funk and bubblegum soul, paired with a 12-year-old Michael Jackson’s precocious singing talent, this track became a righteously rocking holiday classic. A nod to its staying power, the song made its debut on Billboard’s Hot 100 in early 2021 — 50 years after its initial release.

Schmaltz Factor: 5. Lyrically, the song could be read as a stern warning to kids around the world eagerly awaiting Christmas Eve. However, Michael’s youthful falsetto, alongside the group’s exuberant harmonies, inject the song with an enduring vitality. — J.N.

Saturday Night Live Cast, “I Wish It Was Christmas Today” (2000)

Holiday 100 Peak: N/A

Why It’s a Gift: The joke of this 2000 SNL sketch song exists in the childlike simplicity of the musicianship, the dancing and the lyrics (“I wish it was Christmas today/ In the good old U-S of A”.) But for anyone who grew up on early 2000s SNL, “I Wish It Was Christmas Today” — performed by Horatio Sanz, Jimmy Fallon, Chris Kattan and Tracy Morgan — is simultaneously laugh-out-loud funny, legitimately catchy and, like so many of the best parts of Christmas, totally nostalgic.

Schmaltz Factor: 2, because it’s almost impossible to be schmaltzy and self-aware at the same time, and everyone involved in this sketch — from the four comedians who’ve performed it a half dozen times on SNL over the years, to Julian Casablancas, who covered it in 2009 — is totally conscious that this one is just pure fun. — K.B.

Justin Bieber, “Mistletoe” (2011)

Holiday 100 Peak: No. 1 (Jan. 2012)

Why It’s a Gift: Bieber makes his teen heartthrob status adaptable for “the most beautiful time of the year,” while making his listeners feel like they’re the apple of his eye in the swoon-worthy 2011 holiday love song.

Schmaltz Factor: 8. The song about an innocent kiss at Christmastime has quite the nod to Bieber’s unwavering Christian faith when he sings in the bridge, “Ayy love, the wise men followed the star/ The way I followed my heart/ And it led me to a miracle.” — H.M.

The Pogues feat. Kirsty MacColl, “Fairytale of New York” (1987)

Holiday 100 Peak: N/A

Why It’s a Gift: Over a majestic waltz, dreams of romance and Broadway turn into realities of breakup and the Bowery. As sweeping as it is ultimately heartbreaking, “Fairytale of New York” has become as close to a Christmas standard as any song from a band as Hallmark-unfriendly as Irish punks The Pogues could possibly be.

Schmaltz Factor: 3. The strings and bagpipes pack a dewy-eyed emotional wallop, but the song’s sweetness turns to sandpaper by the wince-inducing use of the hard “f” word in the combative second-to-last verse, and by the gut-wrenching back and forth between MacColl and Pogues frontman Shane McGowan that begins the concluding one: “I could’ve been someone/ Well, so could anyone.” — A.U.

Gene Autry, “Rudolph the Red-Nosed Reindeer” (1949)

Holiday 100 Peak: No. 7 (Dec. 2018)

Why It’s a Gift: This tale of a bullied reindeer who becomes the story’s hero after leading Santa’s team through a foggy Christmas Eve thanks to his shiny red nose is an enduring classic. It’s a relatable message for any child who has felt lonely and left out by other kids.

Schmaltz Factor: 8. The song’s subject matter, coupled Autry’s earnest, calm delivery can make for a cloying track, even if it is aimed at children. — J.N.

Band Aid, “Do They Know It’s Christmas” (1984)

Holiday 100 Peak: No. 14 (Dec. 2011)

Why It’s a Gift: Band Aid came together with the best intentions — if not always the best lyrics — to record this plea for a moment of universal holiday selflessness in 1984, a rare (effective) Christmas song that gives more consideration to the world outside the homestead than the one within. The song’s legacy is complicated, but the feeling it inspires isn’t, and as an early-MTV-era U.K. pop production and cultural snapshot, it’s absolutely peerless.

Schmaltz Factor: 10. Again, nothing schmaltzy about the subject of Ethiopian famine, but the song’s first line of defense against the issue is a level of cheese rarely heard before or since, peaking with the singalong outro: “Feeeeeed theeeee WO-ORLD!/ LET THEM KNOW IT’S CHRISTMAS TIME AGAIN!” — A.U.

Kurtis Blow, “Christmas Rapping” (1979)

Image Credit: Courtesy Photo

Holiday 100 Peak: N/A

Why It’s a Gift: The first major Christmas rap single was a standard-setter in all sorts of ways, with a disco groove that could’ve worked on the dancefloor any time of the year and Blow’s typically high-energy bars proving indeed that “this ain’t 1823 — ain’t even 1970.” It became a cultural staple in such short order that it was sampled by songs as far-flung as Public Enemy’s cautionary tale “Night of the Living Baseheads” a decade later — and then Next’s Hot 100-topping erection apology “Too Close” a decade after that.

Schmaltz Factor: 6. Blow’s Yuletide swagger probably caused some broken monocles in ’79 among those used to Bing Crosby and Nat King Cole, but after 40-plus years of rap outliving its fad predictions, its lessons about “not concealing the way you you feel about your friends” feels pretty sappy indeed. — A.U.

Pretenders, “2000 Miles” (1984)

Holiday 100 Peak: N/A

Why It’s a Gift: Lead Pretender Chrissie Hynde gives one of the great performances in holiday music history on this lonesome ballad, with her bleary-eyed, octave-bounding vocal giving unimaginable emotional heft to lyrics as simple as “He’s gone/ 2000 miles/ It’s very far.” As chiming guitar falls around her like sheets of snow, Hynde tries to keep the faith that “he’ll be back at Christmastime,” but she’s far more believable as she resigns herself in the song’s devastating bridge: “I’ll think of you wherever you go.”

Schmaltz Factor: 6. It’s as tearjerking a holiday torch song as they come, but there’s an unmistakable dignity to Hynde’s vocal that remains even at its most desperate. — A.U.

Paul McCartney, “Wonderful Christmastime” (1979)

Holiday 100 Ranking: No. 15 (Dec. 2018)

Why It’s a Gift: Paul was attacked by critics in the ’70s for giving the world light, joyous pop fare after his culture-shifting run with The Beatles in the ’60s. But when you take that yule log out of your ass, it’s hard to deny the charming ebullience of McCartney‘s seasonal synth sing-along. Like his best, its deceptive simplicity makes it an evergreen delight.

Schmaltz Factor: 8. Trying to keep the schmaltz out of a McCartney song is like withholding presents from children on Christmas Eve; sure, you can do it, but why not let a perfect pairing do its thing? The sweet, childlike holiday wonder of this 1979 single has a perfect counterpoint in the primitive, echo-laden synths that make “Christmastime” weirdly sentimental and strange at the same time. — J. Lynch

Kelly Clarkson, “Underneath the Tree” (2013)

Holiday 100 Peak: No. 8 (Jan. 2014)

Why It’s a Gift: If Kelly Clarkson’s full-length Wrapped in Red in an underrated holiday treasure, then “Underneath the Tree” is the shimmering diamond at it’s center. The boisterous big-band sound, optimistic lyrics and Clarkson’s unwavering vocals made “Underneath the Tree” an instant classic the moment it was released back in 2013.

Schmaltz Factor: 6. The key word here is earnest. Clarkson’s performance is sentimental and filled with the sort of Christmas cheer that gets us feeling all ooey-gooey around the holidays — lyrics like “Presents, what a beautiful sight/ Don’t mean a thing if you ain’t holding me tight” certainly bring the song’s number up. But rarely does Clarkson dip into performative overproduction; it’s a little mushy, yet you can’t help but believe what she’s singing. — S.D.

Burl Ives, “A Holly Jolly Christmas” (1964)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 3 (Dec. 2019)

Why It’s a Gift: For multiple generations, this boppy little jam is the sonic personification of the entire holiday season. Originally recorded by The Quinto Sisters in 1964, singer, actor and American folk song authority Burl Ives jingled-jangled it into ubiquity when he delivered his velvet-voiced rendition for the 1964 stop motion masterpiece Rudolph the Red-Nosed Reindeer. December hasn’t been the same since.

Schmaltz Factor: 9. A 20th century folk song in its own right, to the cynical ear “A Holly Jolly Christmas” is almost deliriously saccharine, but it’s got all the warmth, cheer and soothing innocence of Christmas baked right into it. — K.B.

Stevie Wonder, “What Christmas Means to Me” (1967)

Holiday 100 Peak: No. 51 (Jan. 2021)

Why It’s a Gift: In the middle of Stevie Wonder’s late-‘60s run of smashes came his first holiday album, 1967’s Someday at Christmas, and a bauble of joy titled “What Christmas Means to Me,” on which Wonder sounds giddy while listing his favorite details of the holiday season amidst a jaunty piano line, tinkling bells and his signature harmonica.

Schmaltz Factor: 8. “What Christmas Means to Me” moves briskly enough to not get bogged down in sentimentality, but tons of emotional modern holiday songs have descended from its listing of mistletoe, choirs and snow, as Wonder’s romantic depiction of the season is enough to sweep up any casual listener. — J. Lipshutz

*NSYNC, “Merry Christmas, Happy Holidays” (1998)

Holiday 100 Peak: No. 37 (Jan. 2016)

Why It’s a Gift: Nothing gives “’90s Christmas” like singing along to this poppy holiday singalong on your sky-blue Sony boombox. Released in 1998, the early *NSYNC track managed to gain classic status, sure to stick around as the embodiment of Y2K cheer for decades to come.

Schmaltz Factor: Considering how representative of the top 40 vanguard this track was when it was released, it’d have to be about a 6. Today though, it’s the quintessential cheesy ’90s holiday jam. — N.R.

Eartha Kitt with Henri René and His Orchestra, “Santa Baby” (1953)

Holiday 100 Peak: No. 18 (Dec. 2013)

Why It’s a Gift: Claiming to be “an awful good girl,” Kitt stirred up some controversy in ’50s-era America by seductively serenading listeners with her wish list to the title character in 1953’s “Santa Baby.” She inquires about “a 54 convertible” in light blue — and of course, “one little thing, a ring” as she summons him to “hurry down the chimney tonight.” Sixty-eight years after first hitting the airwaves, the song’s sex appeal endures — especially since these days, nothing is sexier than a woman who knows exactly what she deserves.

Schmaltz Factor: 8. As soon you hear the intro of “Ba boom, ba boom, ba boom,” you know it’s going down when all the ladies turn to their significant others and give them an inquiring look complete with a raised eyebrow — hinting at their own Christmas wish list. A ring, maybe? ‘Tis the season, after all. — MIA NAZARENO

John Lennon & Yoko Ono With the Harlem Community Choir, “Happy Xmas (War Is Over)” (1971)

Holiday 100 Peak: No. 9 (Dec. 2011)

Why It’s a Gift: For a holiday filled with musty platitudes and gift-giving anxiety, leave it to the late Beatle and his musical partner/wife to celebrate with this iconic combo homage to the season and Vietnam War protest. The 1971 single was part of the couple’s years-long promotion of peace, and it allowed Lennon to spike his activism with some sweet holiday sentiments in lines such as “And so happy Christmas for black and for whites/ War is over, if you want it/ For the yellow and red ones/ Let’s stop all the fight/ War is over now.”

Schmaltz Factor: 4. Lennon wrapped his serious message in recognizably cheery holiday trappings — sleigh bells, the Harlem Community Choir and swelling strings. But even as he wished you a happy holiday, biting lines about conflict and fear lurk around every corner, topped by the swelling, indelible mantra the couple posted on billboards around the world at the time: “War is over/ If you want it.” — G.K.

Chuck Berry, “Run Rudolph Run” (1958)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 9 (Jan. 2021)

Why It’s a Gift: There was a time when rock’n’roll and Christmas would have felt like conflicting themes, but Chuck Berry was up to the task of bridging them. With Berry’s signature guitar riffs, “Run Rudolph Run” could melodically fit on any secular rock record, but his whimsical lyrics of “Rudolph whizzin’ like a shootin’ star” make it a holiday staple.

Schmaltz Factor: 8. “Run Rudolph Run” may sound like Berry hits including “Johnny B. Goode,” but the track goes way up on the schmaltz factor when he suggests Rudolph the reindeer take the freeway to town. — T.M.

Bobby Helms, “Jingle Bell Rock” (1957)

Holiday 100 Peak: No. 2 (Dec. 2016)

Why It’s a Gift: Sure, the lyrics aren’t particularly complicated, nor do they always make perfect sense, but with Helms’ country influence and well-timed guitar twang, “Jingle Bell Rock” is a feel-good song that puts people in the festive spirit — and as of late, has translated to more Hot 100 success than ever, reaching a new No. 3 high on the chart in January 2020.

Schmaltz Factor: 7. The underlying sleigh bells ringing throughout the entirety of the song bumps up the score a few notches. Plus, despite Helms proclaiming “That’s the Jingle Bell Rock” twice throughout the song, most listeners would likely still be hard-pressed to define it. — J.G.

The Waitresses, “Christmas Wrapping” (1981)

Holiday 100 Peak: No. 67 (Dec. 2018)

Why It’s a Gift: “Christmas Wrapping” is the most — the only? — practical and true-to-adult-life Christmas story song ever released, treating the holidays as what they are for most folks over the age of 18: one more thing to make room for on an already-overbooked calendar. Supported by a lively new wave boogie and an indefatigable horn hook, lead Waitress Patty Donahue speak-sings about having no plans for Dec. 25 beyond survival with her sanity intact, declaring on the refrain, “Merry Christmas/ But I think I’ll miss this one this year.”

Schmaltz Factor: 4. Though it spends most of its runtime as the least-sentimental popular Christmas song since Thurl Ravenscroft, it does wind down to a rather hard-earned “very happy ending” — as Donahue links up at the last second with a guy who’s also spending the holidays alone, and ultimately changes her tune to “Merry Christmas/ Couldn’t miss this one this year.” — A.U.

Joni Mitchell, “River” (1971)

Holiday 100 Peak: N/A

Why It’s a Gift: It’s been 50 years since listeners first heard the opening solo piano notes to “Jingle Bells,” shifting into a minor key, to introduce “River,” from Joni Mitchell’s landmark 1971 album Blue. With homesick lyrics by the Canadian-born California transplant (“It don’t snow here/ It stays pretty green”), the song soars on Mitchell’s soprano with one of pop music’s most evocative holiday lyrics of longing and regret: “I wish I had a river I could skate away on.”

Schmaltz Factor: 3. The song “redefined the way people look at Christmas music,” Brandi Carlile told her Carnegie Hall audience last month where she performed Blue in its entirety. “There needed to be a song that embraces the sorrow of Christmas.” — T.D.

The Beach Boys, “Little Saint Nick” (1963)

Holiday 100 Peak: No. 25 (Dec. 2017)

Why It’s a Gift: This enduring hit, which shares melodic and rhythmic elements with the group’s “Little Deuce Coupe” from earlier that year, gives a holiday slant to The Beach Boys’ trademark harmonies and penchant for lyrics about classic cars, this time around envisioning Santa’s sleigh as a candy apple red hot rod. The group followed the song’s success by releasing a Christmas album the following year.

Schmaltz Factor: 5. This upbeat confection has plenty of verve, though the group’s reedy, sugary harmonies mixed with sleigh bells and glockenspiel at times teeters on the edge of saccharine. — J.N.

Judy Garland, “Have Yourself a Merry Little Christmas” (1944)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 87 (Jan. 2019)

Why It’s a Gift: In a poignant scene from the 1944 movie musical Meet Me in St. Louis, Judy Garland introduces the now-classic, promising her kid sister that they’ll “muddle through somehow” as their family plans to move away from their beloved hometown. While the bulk of Christmas music is about the happy side of the festivities, the bitter reality is that the season can also be heartbreakingly painful, so a lot of people can relate to this melancholy-yet-hopeful ballad delivered with Garland’s reassuring, velvety voice.

Schmaltz Factor: 4. It is from a musical, after all, so Garland’s impassioned delivery is to be expected, but mostly this is an unfussy affair. — K.A.

Andy Williams, “It’s the Most Wonderful Time of the Year” (1963)

Holiday 100 Peak: No. 2 (Dec. 2018)

Why It’s a Gift: Andy Williams’ declaration of love for the holiday season is the unofficial theme song for Christmas. It plays at every department store on loop, it’s inescapable on the radio and even Will Ferrell parodied it – all for good reason. It embodies what makes Christmas so special: time spent with family, snow on the ground, mistletoe at cocktail parties and an overall sense of joy. It truly captures the “hap-happiest season of all.”

Schmaltz Factor: 10/10. Maybe even 11. The most schmaltziest schmaltz of them all. From gushing over the “parties for hosting/ marshmallows for toasting/ and caroling out in the snow,” to the “Ding Dong, Ding Dong” backup vocals and the jingle bells over the instrumentals, it’s like Santa flew in on his sleigh from the North Pole and wrote the song himself. — R.A.

Ariana Grande, “Santa Tell Me” (2014)

Holiday 100 Peak: No. 1 (Jan. 2015)

Why It’s a Gift: Despite the endless comparisons throughout her career to the Undisputed Queen of Christmas Mariah Carey, Ariana Grande did manage to stand out from her peers with 2014’s “Santa Tell Me.” A light-hearted, soft-pop jam, the twinkling, sleigh bell-infused single sees Ariana flipping the classic trope of asking Santa for a boyfriend on its head, instead making sure he’s not just going to send her another loser. It’s the kind of Christmas song that manages to worm its way in between some of the bigger, bouncier classics and just politely enjoy its stay in your head — and on the charts.

Schmaltz Factor: 4. When it comes to Ariana’s voice, “over the top” isn’t exactly a phrase that comes to mind. Grande keeps the song relatively mellow throughout, never quite letting the holiday spirit boil over into the treacly trappings of other holiday hits. — S.D.

Elvis Presley, “Blue Christmas” (1957)

Holiday 100 Peak: No. 12 (Jan. 2013)

Why It’s a Gift: “Blue Christmas“ had been a hit in the ’40s and early ’50s for artists like Ernest Tubb and Russ Morgan, but with one quivering “I’ll… have… a… bluuuuuuue… Christmas… without you…” — accompanied by gorgeous backing wheezes from the Jordanaires — the sublimely melancholy classic became The King’s for all time.

Schmaltz Factor: 6. The song is short and sweet, and Elvis’ delivery avoids histrionics, but “You’ll be doing all right, with your Christmas of white/ But I’ll have a blue, blue, blue Christmas” does lay it on a little thick. (Plus, who ever heard of “blue snowflakes”?) — A.U.

Vince Guaraldi Trio, “Christmas Time Is Here” (1965)

Holiday 100 Peak: No. 17 (Jan. 2017)

Why It’s a Gift: The 1965 TV special A Charlie Brown Christmas is such a seasonal staple that it’s easy to overlook the unlikely fact that a half-hour TV special based on the intelligent but hardly edgy Peanuts comic strip gave us the pinnacle of Christmas jazz cool. The six-minute instrumental version of “Christmas Time Is Here” is the star on top of this tree; the song’s languid yet inventive ivory tickling and that brush-on-drum technique ensure that this ostensible background music is always cooler than whatever is happening in the foreground of your festive fete. No wonder its parent set is Billboard‘s No. 1 Greatest of All Time Holiday Album.

Schmaltz Factor: 2. Even on the vocal version of “Christmas Time Is Here” with the children’s choir, there’s a clinical detachment to the delivery that keeps it from veering into proper schmaltz. Like Charles M. Schulz’s Peanuts strip, the Vince Guaraldi Trio’s music is suited for everyday Americana without personifying it. It’s a loving, heartfelt tribute to Christmas that doesn’t kowtow to its commercial expectations. — J. Lynch

Donny Hathaway, “This Christmas” (1970)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 25 (Jan. 2014)

Why It’s a Gift: Soul pioneer Hathaway’s prodigious talents as a songwriter, arranger, musician and vocalist perfectly capture the joy, fun, blessings and love that embody the spirit of the holiday season, set to an upbeat groove: “Presents and cards are here/ My world is filled with cheer and you/ This Christmas.”

Schmaltz Factor: 2. While everyone from Destiny’s Child and Pentatonix to John Travolta and Olivia Newton-John have covered this upbeat song with varying degrees of success — and schmaltz — none can eclipse Hathaway’s original take: a heartfelt holiday anthem for Black America that’s since become a popular modern standard. — G.M.

Bruce Springsteen, “Santa Claus Is Coming to Town” (1982)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 16 (Jan. 2012)

Why It’s a Gift: This 1934 standard has been covered by a fleet of heavyweights including The Jackson Five, The Supremes, Michael Bublé and Mariah Carey, but no rendition captures the rip-roaring excitement over Santa Claus’ impending arrival better than Springsteen’s boisterous 1975 live version, which features copious bells, a festive sax solo and America’s Dad riffing on how everyone in the audience is in trouble for not being good this year.

Schmaltz Factor: 5. Bruce is in full showman mode here, upping the cheese factor with those aforementioned bells and a riff about “the wind ripping down the boardwalk,” but anyone who doesn’t crack a smile when this one comes on is just plain miserly. (This writer wasn’t the only person in the audience crying Christmas morning-style happy tears when Springsteen & The E Street Band played “Santa Claus Is Coming To Town” during their encore at Bonnaroo 2009. In June. In the 90-degree heat. Pure joy.) — K.B.

Run-D.M.C., “Christmas in Hollis” (1987)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 22 (Jan. 2014)

Why It’s a Gift: Kurtis Blow’s 1979 “Christmas Rappin’” and the Treacherous Three’s 1984 “Xmas Rap” featuring Kool Moe Dee arrived first, but “Christmas in Hollis” quickly became the holiday’s definitive hip-hop song, Set in the then-primarily Black Queens, New York neighborhood of the title, where “Mom’s cooking chicken and collard greens,” Rev. Run and Darryl McDaniels melded their hard-edged rap style and a sample of Clarence Carter’s horny soul classic “Back Door Santa” with traditions and songs previously associated with the Bing Crosby crowd: eggnog, a yule log and interpolations of “Jingle Bells” and “Joy to the World.”

Schmaltz Factor 2. The song’s not exactly tougher than leather, but its hip-hop soul keeps the yuletide joy in check, as exemplified by the lyric, “The rhymes you hear are the rhymes of Darryl’s, but each and every year we bust Christmas carols.” — F.D.

José Feliciano, “Feliz Navidad” (1970)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 3 (Jan. 2012)

Why It’s a Gift: Feliciano wrote what he calls the “first ever bilingual Christmas song” in 1970 in the middle of summer in Los Angeles, in part because he felt homesick for Puerto Rico. The English lyrics were added to ensure radio play, but truth is, Feliciano didn’t think much of a song that he hammered out in minutes. However, the irresistible “Feliz Navidad” proved the gift that kept on giving, rising in popularity every year to achieve cult status. Today, it’s a favorite in two languages.

Schmaltz Factor: 7. Feliciano’s deadpan delivery contrasts with lyrics that go from childish to heartfelt: “I wanna wish you a Merry Christmas, from the bottom of my heart.” — L.C.

Brenda Lee, “Rockin’ Around the Christmas Tree” (1958)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 2 (Dec. 2012)

Why It’s a Gift: Little Miss Dynamite was just 13 when she recorded and first released this enduring holiday party-starter in 1958. The reference in the song’s title to rock, then just a few years old, and the rock and roll and rockabilly accents on the backing track gave this record a timely quality back then, and now are charmingly retro.

Schmaltz Factor: 4. It’s not without its holiday sentimentality, but you probably love this record even if you wouldn’t be caught dead caroling and would (inexplicably) pass up a piece of pumpkin pie. — P.G.

Bing Crosby, “White Christmas” (1947)

Image Credit: courtesy Photo

Holiday 100 Peak: No. 5 (Dec. 2015)

Why It’s a Gift: Easily one of the finest pop compositions of the 20th century, “White Christmas” was recorded by Bing Crosby for the 1942 musical Holiday Inn but better is known by his nearly identical 1947 version. It’s a song written by a Jewish-Russian immigrant (Irving Berlin) and performed by America’s first true multi-media sensation (Crosby), which provided solace to overseas U.S. troops during World War II. In other words, it’s not just an exemplar of Christmas music, but of America at its best. Countless others have covered it, but in the hands of Crosby — who once sang it to American troops who would never return home — it attained immorality. With 50 million copies sold worldwide, it’s still the biggest physical single of all time, period.

Schmaltz Factor: 5. Thanks to Berlin’s deft lyrical detail and simplicity, it’s hardly hokey. Of course, “White Christmas” is inarguably sentimental, but in the right hands – such as Crosby’s – it’s a melancholy, even elegiac meditation on the simple things that make life worth living, even if you only realize it from afar. — J. Lynch

Wham!, “Last Christmas” (1984)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 3 (Dec. 2019)

Why It’s a Gift: Released by Wham! when the U.K. duo — principally, of course, singer and writer/producer George Michael — were at the very peak of their international pop powers, “Last Christmas” is likely the brightest jewel in the act’s catalog, a never-again torch song with an immaculate synth-pop sheen and a true broken-heartbeat at its core. As always, no one illustrates the helplessness of misguided affection better than Michael — “Now I know what a fool I’ve been/ But if you kissed me now, I know you’d fool me again” — but the song burns just as brightly decades later because of how the holiday spirit inspires him to try harder and do better: “Next year, to save me from tears, I’ll give [my heart] to someone special.”

Schmaltz Factor: 7. Undoubtedly, the song leans into the drama harder with each successive “You gave it/me awayyyyy” — and the ski chalet-set video is cheese central, natch — but the thing that gives the song its most stomach-dropping resonance these days is undoubtedly the memory of Christmas 2016. — A.U.

Nat King Cole, “The Christmas Song (Merry Christmas to You)” (1961)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 2 (Jan. 2014)

Why It’s a Gift: With a voice like hot chocolate poured over a lush string arrangement, there’s only one word for Nat King Cole’s recording of “The Christmas Song“: warm. The definitive version of the classic, which Cole’s jazz trio introduced in 1946, wraps listeners up in a thick wool blanket as they sit fireside roasting chestnuts, even as it invokes ice-cold images of Jack Frost and Eskimos. It’s no wonder that the song is generically titled “The Christmas Song,” because it perfectly encapsulates the best of Christmas music with its sense of homey familiarity and cozy warmth. (The marshmallows on top? That little taste of the “Jingle Bells” melody to wrap it up in a bow.)

Schmaltz Factor: 3 – Nat King Cole’s earnest delivery and the song’s understated string-and-piano production make for a timelessly tasteful listen. – K.A.

Darlene Love, “Christmas (Baby Please Come Home)” (1963)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 13 (Dec. 2020)

Why It’s a Gift: The centerpiece of one of the finest holiday albums ever made — Phil Spector’s 1963 A Christmas Gift for You from Philles Records set — Love’s signature song is a layered, lush pop symphony from first note to the last. Between Spector’s famed Wall of Sound and Love’s full-throttled vocals,  begging that her baby return home so they can frolic like they did last year, the song wraps itself around you like a warm, flannel Christmas blanket.

Schmaltz Factor: 1.  Nothing schmaltzy here… just the buoyant melody playing counterpoint to Love’s unparalleled vocals that still feels like a revelation every time the opening bells ring. — M. Newman

Mariah Carey, “All I Want For Christmas Is You” (1994)

Image Credit: Courtesy Photo

Holiday 100 Peak: No. 1 (Dec. 2011)

Why It’s a Gift: The twinkling percussion and the Queen of Christmas’ warm sugar “I-I-I don’t want a lot for Christmas” ballad-like intro have ushered in each of the last 28 Christmas seasons. And the ubiquitous 1994 yuletide carol just picks up from there, as the ’60s-inspired groove trots to the beat of church- and sleigh-like bells, and soars with her wintery whistle tones as she sings, “Oh baby, all I want for Christmas is youuuuuuuuu!!“

Schmaltz Factor: 10. “All I Want For Christmas Is You” is all about wanting a significant other more than anything for the holidays, and expert singer/songwriter Carey somehow manages to capture that warm, fuzzy feeling with almost Scrooge-like statements like “I don’t care about the presents underneath the Christmas tree” and “I don’t need to hang my stocking there upon the fireplace.” Of course, those aren’t about being anti-festive, but simply about Carey’s wishlist remaining focused on receiving the ultimate gift: love. — H.M.

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Louis Armstrong and the Commanders, “Zat You, Santa Claus?” (1953)

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Johnny Mathis, “The Sounds of Christmas” (1963)

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!!!, “And Anyway It’s Christmas” (2013)

Dan Fogelberg, “Same Old Lang Syne” (1980)

Destiny’s Child, “Carol of the Bells” (a.k.a. “Opera of the Bells”) (2001)

Pansy Division, “Homo Christmas” (1992)

The Flaming Lips, “A Change at Christmas (Say It Isn’t So)” (2003)

Mecano, “Un Año Más” (1988)

Tom Petty and the Heartbreakers, “Christmas All Over Again” (1992)

Willie Nelson, “Pretty Paper” (1964)

Kate Bush, “December Will Be Magic Again” (1980)

Fats Domino, “I’ll Be Home For Christmas” (1993)

Alexander O’Neal, “Our First Christmas” (1988)

Dean Martin & Marilyn Maxwell, “Baby It’s Cold Outside” (1949)

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Kacey Musgraves, “Christmas Makes Me Cry” (2016)

Tony Bennett, “Winter Wonderland” (1968)

Carla Morrison, “Jesús” (2016)

Dolly Parton, “Hard Candy Christmas” (1982)

The Ronettes, “Sleigh Ride” (1963)

Perry Como, “(There’s No Place Like) Home For the Holidays” (1954)

Sufjan Stevens, “That Was the Worst Christmas Ever!” (2006)

Hector Lavoe y Willie Colón, “Aires de Navidad” (1970)

Simon & Garfunkel, “7 O’Clock News/Silent Night” (1966)

Nat King Cole, “O Come All Ye Faithful” (1960)

De La Soul, “Millie Pulled a Pistol on Santa” (1991)

Eagles, “Please Come Home For Christmas” (1978)

Marco Antonio Solís / Los Bukis, “Navidad Sin Ti” (1987)

Celine Dion, “O Holy Night” (1998)

Bing Crosby & The Andrews Sisters, “Mele Kalikimaka (Merry Christmas)” (1950)

Andy Williams, “Happy Holiday/The Holiday Season” (1963)

James Brown, “Santa Claus Go Straight to the Ghetto” (1968)

Stevie Wonder, “Someday at Christmas” (1966)

U2, “Christmas (Baby Please Come Home)” (1987)

Vince Guaraldi Trio, “O Tannenbaum” (1965)

Clarence Carter, “Back Door Santa” (1968)

Pandora, “Los Peces en el Rio” (1986)

Whitney Houston, “Do You Hear What I Hear?” (1987)

Charles Brown / Johnny Moore’s Three Blazers, “Merry Christmas Baby” (1956)

The Chipmunks With David Seville, “The Chipmunk Song (Christmas Don’t Be Late)” (1958)

Michael Bublé, “It’s Beginning to Look a Lot Like Christmas” (2011)

Prince, “Another Lonely Christmas” (1984)

The Muppets, “We Need a Little Christmas” (1987)

The Jackson 5, “I Saw Mommy Kissing Santa Claus” (1970)

Taylor Swift, “Christmases When You Were Mine” (2007)

The Drifters, “White Christmas” (1954)

Ramones, “Merry Christmas (I Don’t Want to Fight Tonight)” (1987)

Merle Haggard, “If We Make It Through December” (1973)

The Temptations, “Silent Night” (1980)

Kanye West feat. CyHi da Prynce & Teyana Taylor, “Christmas in Harlem” (2010)

Los Tigres del Norte, “Navidad de los Pobres” (1993)

Elton John, “Step Into Christmas” (1973)

Otis Redding, “Merry Christmas Baby” (1967)

Frank Sinatra, “Have Yourself a Merry Little Christmas” (1957)

The Ronettes, “Frosty the Snowman” (1963)

Carpenters, “Merry Christmas Darling” (1970)

The Kinks, “Father Christmas” (1977)

Ella Fitzgerald, “Let It Snow! Let It Snow! Let It Snow!” (1960)

El Gran Combo de Puerto Rico, “No Hay Cama Pa’Tanta Gente” (1988)

Thurl Ravenscroft, “You’re a Mean One, Mr. Grinch” (1966)

Bing Crosby & David Bowie, “Peace on Earth/Little Drummer Boy” (1977)

The Jackson 5, “Santa Claus Is Coming to Town” (1970)

Saturday Night Live Cast, “I Wish It Was Christmas Today” (2000)

Justin Bieber, “Mistletoe” (2011)

The Pogues feat. Kirsty MacColl, “Fairytale of New York” (1987)

Gene Autry, “Rudolph the Red-Nosed Reindeer” (1949)

Band Aid, “Do They Know It’s Christmas” (1984)

Kurtis Blow, “Christmas Rapping” (1979)

Pretenders, “2000 Miles” (1984)

Paul McCartney, “Wonderful Christmastime” (1979)

Kelly Clarkson, “Underneath the Tree” (2013)

Burl Ives, “A Holly Jolly Christmas” (1964)

Stevie Wonder, “What Christmas Means to Me” (1967)

*NSYNC, “Merry Christmas, Happy Holidays” (1998)

Eartha Kitt with Henri René and His Orchestra, “Santa Baby” (1953)

John Lennon & Yoko Ono With the Harlem Community Choir, “Happy Xmas (War Is Over)” (1971)