10 Most Rewatchable 2010s Rom-Coms, Ranked

The Big Picture

• Romantic comedies like ‘Crazy Stupid Love’ and ‘Easy A’ offer effortless humor and intimate relationships for an enjoyable watch.
• Movies like ’10 Things I Hate About You’ and ‘Love, Simon’ cater to a wide audience, providing comfort and rewatchability.
• Films such as ‘To All the Boys I’ve Loved Before’ and ‘Crazy Rich Asians’ offer heartwarming stories and relatable characters for a fun movie night.

Romantic comedies are a lighthearted entertainment option for anybody in the mood for a film with humor, the odd bit of drama, and all the romance they could want. They are an easy option to put on in the background or sit down with some friends on a cozy evening, and they’re something everyone can enjoy.

Being something a viewer can have on in the background while they do chores means a movie’s versatility can be one of its strongest features. It’s a sign of a comfort film and proves its rewatchability, even if someone’s attention isn’t solely on the TV as they do other stuff. Movies like the underrated Crazy Stupid Love and the popular Emma Stone-starring Easy A have gripped their audiences for years, with their effortless humor and intimate relationships at the forefront of entertainment. There have been dozens and dozens of success stories in the rom-com genre over the last one hundred years, but these ten are some of the most reliable contenders for a rewatch.

10 ’10 Things I Hate About You’ (1999)

Directed by Gil Junger

10 Things I Hate About You is a twenty-five-year-old teen rom-com from 1999. The film stars the late Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Allison Janney, David Krumholtz, Gabriella Union, and a plethora of other famous faces as they tell the story of a boy who moves to a new high school and comes face to face with the teenage difficulties of love and the comedic problems that can rise.

Award-nominated and positively received by critics and audiences, 10 Things I Hate About You has become a cult classic and garnered quite a following in the years since its release. It served as a breakout role for three of its main actors, propelling Heath, Joseph, and Julia into the spotlight of prominent young performers, and its storyline is easy to get into no matter how many times it’s been on.

Watch on Disney+

9 ‘Love, Simon’ (2016)

Directed by Greg Berlanti

Another teen rom-com with a hint of drama thrown into the mix came eight years ago with the release of Greg Berlanti‘s Love, Simon. The film stars Nick Robinson, who gained recognition following a memorable performance in the first installment of the Jurassic World trilogy back in 2015, as only his second film appearance.

The following year saw him lend his talents to a movie so full of heart that it had audiences hooked from the trailer alone. It tells the story of a young closeted teenager as he deals with the day-to-day life of a teen, a brewing romance, and a blackmailer making his life trouble with threats of outing him. Critically and commercially successful, the film has already reached classic status for many, and its story showcases acceptance of oneself perfectly.

Watch on Disney+

8 ‘To All the Boys I’ve Loved Before’ (2018)

Directed by Susan Johnson

This Netflix original from 2018 took critics and audiences by storm the moment it was released on the platform six years ago. To All the Boys I’ve Loved Before is arguably one of the most rewatchable Netflix original romance movies, as its characters are very relatable and easy to like.

The popularity of the original performed so well that it sparked the creation of a trilogy with two further sequels called To All the Boys: P.S. I Still Love You and To All the Boys: Always and Forever, which did almost as well as their predecessors in the eyes of critics. All three of these films provide an entertaining binge-watch for a movie night full of romance, comedy, and heartfelt interactions between characters that anyone can enjoy.

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7 ‘Set It Up’ (2018)

Directed by Claire Scanlon

Netflix is typically a good streaming platform to gravitate towards when looking for anything someone might be in the mood for. Whether it’s a gripping drama, hilarious comedy, true documentary, or, in this case, a lighthearted rom-com like 2018’s Set It Up, there’s never a lack of things to watch.

The Claire Scanlon-directed romantic comedy from the mind of writer Katie Silberman follows two assistants in New York whose bosses push them to their limits. In an effort to get them to loosen up, the two women (Zoey Deutch and Glen Powell), strangers until they connect over their similar situations, attempt to set them up on dates, with some unexpected results. Positively received by those who saw it in the weeks after its release on the platform, the movie is more than capable of a rewatch thanks to its charismatic characters.

Watch on Netflix

6 ‘The Big Sick’ (2017)

Directed by Michael Showalter

The Big Sick is a multi-award-winning movie from 2017 with a total of sixty-three nominations across dozens of organizations, with categories ranging from Best Original Screenplay and Best Picture to Best Actress and even winning the title of Best Film of the Year from the American Film Institute.

The movie’s plot centers on Kumil Nanjiani‘s fictionalized version of himself as he stars alongside Zoe Kazan as two people who grow closer as the story progresses. The movie is classed as a romantic comedy-drama for the occasional emotional damage it can cause its audience. However, it’s a lighthearted viewing experience more than deserving of all its success.

Watch on Amazon Prime

5 ‘Friends With Benefits’ (2011)

Directed by Will Gluck

Justin Timberlake decided to try his hand at acting before becoming a successful solo artist following his split from NSYNC in 2002. His first on-screen appearance was in the 2000 comedy film Longshot, in which he played himself. But this only gave him a taste of the movie world, and his career as an actor only grew as the years progressed.

In 2011, he starred alongside Mila Kunis as Dylan Harper in the popular rom-com from director Will Gluck. Set against the backdrop of New York, Friends With Benefits follows Dylan and Jamie (Kunis) as they engage in a friendship with the added titular benefits, only for romantic feelings to develop and go ignored by both parties. It’s an entertaining watch with two lead personalities capable of keeping audiences engaged and amused throughout its entirety.

Watch on Netflix

4 ‘Easy A’ (2010)

Directed by Will Gluck

The second movie on this list from director Will Gluck comes with the 2010 release of the iconic Emma Stone-starring Easy A. The film has a star-studded cast whose performances helped aid in its success. Alongside Emma Stone, stars Lisa Kudrow, Stanley Tucci, Dan Byrd, Patricia Clarkson, Aly Michalka, Thomas Haden Church, and many more.

The teen rom-com takes its audiences on an incredibly entertaining journey as The Scarlet Letter-inspired film’s witty dialogue and entertaining plot keep people hooked from the start. Easy A won five awards, many for Emma’s performance of Olivia Penderghast, and earned her her first Golden Globe Award for Best Actor.

Watch on Netflix

3 ‘Crazy Rich Asians’ (2018)

Directed by Jon M. Chu

Box office tycoon Crazy Rich Asians became an instant critical and commercial success after its release six years ago. The Jon M. Chu-directed rom-com grossed a whopping near-eight times its budget of just $30 million when it brought in $239 million, which made it the highest-grossing romantic comedy of the entire decade.

Its success wasn’t undeserved. Cast performances from Constance Wu, Gemma Chan, Henry Golding, Michelle Yeoh, Ken Jeong, Lisa Lu, and Awkwafina were highly praised by critics, with many nominated for various accolades, including Best Acting Ensemble at the Critics Choice Awards. The movie follows a couple who fly to Singapore to meet the country’s most wealthy family, whom Henry’s character, Nick, just so happens to be a part of, unbeknownst to his girlfriend.

Buy on Amazon

2 ‘Always Be My Maybe’ (2019)

Directed by Nahnatchka Khan

Always Be My Maybe was written by Michael Golamco, Ali Wong, and Randall Park, of which the latter two also star in the lead roles as Sasha Tran and Marcus Kim. It also stars Keanu Reeves and many more in supporting roles, but the plot primarily centers on Marcus and Sasha when they reunite after years following a teenage fling.

When it dropped on Netflix in 2019, Always Be My Maybe debuted with a 90% Rotten Tomatoes score and plenty of positive feedback from critics. The leading characters’ charm paved the way for many a favorable viewing and earned Ali Wong a Comedy Movie Star nomination at the People’s Choice Awards for her captivating performance as Sasha.

Watch on Netflix

1 ‘Crazy Stupid Love’ (2011)

Directed by Glenn Ficarra and John Requa

Crazy Stupid Love is a 2011 rom-com from the minds of directors Glenn Ficarra and John Requa and writer Dan Fogelman. It stars Ryan Gosling, Steve Carell, Emma Stone, Julianne Moore, Kevin Bacon, Marisa Tomei, and some talented young performers in a story that had the audience’s attention from the opening scene.

Telling the story of Cal Weaver (Carell) as he deals with the sudden separation from his wife (Moore), Crazy Stupid Love is an incredibly enjoyable journey of life with someone cared for, the love held for them, and for Cal, rediscovering the manhood he lost a long time ago, at least according to Jacob Palmer (Gosling). With strong character development throughout and brilliant portrayals of relationship aspects, this 2011 gem is more than worthy of a rewatch, even if just to see that unexpected and hilarious twist at the end.

Watch on Netflix

NEXT: 30 Best Romantic Comedies of All Time