Jonah Hill’s 10 Best Dramatic Movies, Ranked

Jonah Hill’s career has evolved significantly ever since his breakout role in Superbad back in 2007. Hill had initially been seen as a purely comedic actor and often collaborated with co-stars like James Franco, Seth Rogen, Michael Cera, and Danny McBride. However, Hill has proven in recent years that he can play characters that aren’t just there for comic relief. He has matured as an actor and even managed to prove himself as both a writer and director. In the last few years, Hill helmed the A24 coming-of-age drama Mid90s, the mental health documentary Stutz, and an episode of the HBO historical sports series Winning Time: The Rise of The Lakers Dynasty.

Hill’s transition towards more serious material was well-timed. While he epitomized a certain type of raunchy character with his Superbad performance, he couldn’t just play a character like “Seth” for the rest of his career. It’s to Hill’s credit that he recognized this, as some of his comedy vehicles hadn’t shown his full abilities as an actor. It’s remarkable how much he has grown; who would have guessed that the star of The Sitter and Get Him To The Greek would become an Academy Award-nominated dramatic performer? Here are Jonah Hill’s best dramatic roles, ranked.

10 ‘How To Train Your Dragon’ (2010)

Directed by Dean Deblois

The 2010 animated film How To Train Your Dragon was a breakthrough within the medium. The first film in the popular fantasy series is one of the few “family” films that appeal to both adults and children. How To Train Your Dragon has enough colorful action, goofy humor, and fun characters to engage children; however, the film also deals with themes of cultural stigmatization that are more serious.

Hill has a relatively brief role in the first How To Train Your Dragon film as Snotlout Jorgenson, a childhood friend of Hiccup (Jay Baruchel). While Snotlout may not be the most intelligent Viking in Hiccup’s circle of friends, he is incredibly loyal and supports Hiccup when he’s threatened by his overbearing father, Stoick the Vast (Gerard Butler).

Watch On Prime Video

9 ‘Funny People’ (2009)

Directed by Judd Apatow

Judd Apatow is often criticized for the extended length of his films; there’s rarely a legitimate reason for a comedy film to be longer than 90 minutes. However, Apatow’s 2009 comedy film Funny People is one of the rare films on his resume that actually justifies its extended running time. Adam Sandler gives one of his stronger dramatic performances as George Simmons, a comedian who learns that he is dying of a critical illness.

Hill has a supporting role as George’s friend and fellow comedian, Leo Koenig. While playing a comedian allowed Hill to use some of his comic sensibilities, he was able to make the film’s drama work as George begins to deal with the ramifications of his illness.

Watch On Hulu

8 ‘Hail, Caesar!’ (2016)

Directed by Ethan and Joel Coen

Hail, Caesar! is one of Joel and Ethan Coens’ funniest films, but that doesn’t mean that its intentions aren’t serious. The Coens used their over-the-top version of the “Golden Age of Hollywood” to show how radically different the film industry is in practice compared to more idealized versions. The Coens satirize this period in film history by featuring eccentric caricatures of celebrities, actors, and directors that work for Capitol Pictures.

Hill appears as the bond agent Joseph Silverman, who must do his best to ignore the illustrious swimming star DeeAnna Moran (Scarlett Johansson) when she enters his office. He takes his role so seriously that the rest of the film’s comedy stands out even more in comparison; a departure from his usual persona.

Watch On Hulu

7 ‘True Story’ (2015)

Directed by Rupert Goold

Hill and Franco have co-starred occasionally, but True Story is a much different project than Sausage Party or This Is The End. As the title suggests, the film follows a “true story” about the journalist Michael Finkel (Hill), who conducts a series of interviews with the convicted murderer Christian Longo (Franco). Over the course of Finkel’s research, he finds himself drawn to Longo’s story.

Hill does a great job at showing that Finkel is not everything that he appears to be on the surface. While initially Finkel appears to be sympathetic, he begins to manipulate Longo’s testimony in order to fit within his preconceived notions. Anytime Hill and Franco team up, viewers expect absurd scenarios to occur, but True Story shows that their working relationship can be just as emotional.

Watch On Max

6 ‘Accepted’ (2006)

Directed by Steve Pink

As recent documentaries like Operation Varsity Blues have shown, the college application process is fundamentally flawed. The 2006 coming-of-age drama Accepted explores how challenging it can be for young scholars who struggle to determine their future when they are rejected by their top choices for secondary education.

Hill has an important supporting role as Sherman Schrader, a struggling high school graduate who tries to attend a top university in order to appease his parents. The film served as an early example of Hill’s more mature sensibilities; he was able to add dramatic weight to a film that is otherwise dismissed as a “crowd pleaser.”

Watch On Prime Video

Directed by Gus Van Sant

Don’t Worry, He Won’t Get Far On Foot is a powerful film about the power of healing, and more often than not, laughter is the best medicine. Joaquin Phoenix gives one of his most underrated performances as John Callahan, a cartoonist who was severely injured in a serious car accident. As Callahan adjusts to his new life in a wheelchair, he tries to get sober with the help of his sponsor, Donnie Green (Hill).

Hill does a great job of showing how Green’s frankness appeals to Callahan. Green does not deny his struggles with sobriety, and his matter-of-fact attitude is just what Callahan needs during this difficult period in his life. Director Gus Van Sant treats these intimate issues with respect as he explores the addiction and recovery process.

Watch On Prime Video

4 ‘I Heart Huckabees’ (2004)

Directed by David O. Russell

Even though I Heart Huckabees was Hill’s feature film debut, it manages to encapsulate all the genre hallmarks that he would pursue later in his career. Dustin Hoffman and Lily Tomlin star as a pair of “existentialist detectives” who attempt to help their clients use transcendentalism to solve their personal problems. I Heart Huckabees satirizes corporate culture and American pop culture, but at times it’s weird just for the sake of it.

Unfortunately, I Heart Huckabees’ production wasn’t nearly as pleasant as the film itself ended up being. Director David O. Russell earned a reputation for being “hard to work with” after reports circulated about his toxic behavior on the set of the film. Regardless, Hill proved his talent as a serious actor, working alongside Hollywood legends like Hoffman and Tomlin.

Rent On Amazon

3 ‘War Dogs’ (2016)

Directed by Todd Phillips

War Dogs wasn’t just a dramatic departure for Hill; it was also the first non-comedy film by director Todd Phillips. Phillips worked strictly within the comedy genre through his work on Old School and The Hangover trilogy, but later earned an Academy Award nomination for Best Director for his work on the 2019 comic book film Joker. War Dogs was the film that proved that Phillips, like Hill, was more than just a comic artist.

War Dogs centers on the American arms dealers Efraim Diveroli (Hill) and David Packouz (Miles Teller), who begin traveling to the Middle East to deal with advanced weapons technology. Hill does a great job at making Efraim as unlikable as possible; he shows no consideration for the countless lives that his work threatens. It’s impressive that an actor as inherently likable as Hill was able to sink his teeth into the role and play a real-life monster.

Watch On Hulu

2 ‘Moneyball’ (2011)

Directed by Bennett Miller

Moneyball is arguably the film that proved that Hill was a capable dramatic actor. The 2011 sports biopic starred Brad Pitt as Billy Beane, the manager of the Oakland A’s. Beane introduces a groundbreaking new baseball strategy that uses math to come up with the ideal “winning team.” Although Beane’s ideals are initially dismissed by skeptics within the sports industry, his strategy is proven effective after the Oakland A’s win a series of successive victories.

Hill co-stars as Peter Brand, Beane’s assistant and only real ally in the team. Even though Beane constantly has to silence his doubters when promoting his strategy, Brand remains loyal to him. Hill’s performance earned him his first Academy Award nomination for Best Supporting Actor.

Watch On Prime Video

1 ‘The Wolf of Wall Street’ (2013)

Directed by Martin Scorsese

Working with the great Martin Scorsese is a treat for any actor, and The Wolf of Wall Street is certainly one of the director’s more unique projects. Based on the shocking true story, the film follows the notorious Wall Street scammer Jordan Belfort (Leonardo DiCaprio), who defrauded his shareholders by convincing them to buy unsustainable stocks. The Wolf of Wall Street showed how influential men like Belfort and his cronies were able to get away with their crimes through the power of influence.

Hill has a supporting role as Donnie Azoff, Jordan’s right-hand man. Donnie is just as ruthless as Jordan, and perhaps even more cunning. Even though Donnie’s behavior gets pretty ridiculous at times, Hill never makes him feel like a joke; it’s obvious that his crimes are actually ruining people’s lives. Hill’s performance earned him a second Academy Award nomination for Best Supporting Actor; with all due respect to Jared Leto in Dallas Buyers Club, it’s an award he should have won.

Watch On Netflix

KEEP READING: In Jonah Hill’s ‘Stutz,’ Filmmaking Is a Metaphor for Exploring One’s Mental Health