Over the course of his varied career, Jonah Hill has appeared in everything from lowbrow comedies to Oscar-nominated features. Though he may have started off with small supporting roles in flicks like 40-Year-Old Virgin and Knocked Up, the actor has since proven himself a major Hollywood player, taking on versatile gigs that showcase both his impressive comedic timing and dramatic acting chops. Here’s a look back at seven of the most memorable roles of Hill’s career (listed in chronological order).
Hill’s real breakout moment came in this 2007 comedy, in which he starred opposite Michael Cera. While the film’s premise isn’t exactly groundbreaking (two teens try to find a way to buy alcohol so they can attend a party that will make them friends with the “cool” crowd before they leave for college), the chemistry between the two leads, combined with great writing, made this film a surprise hit. In addition to earning critical praise for his spot-on delivery of outlandish line after outlandish line, Hill also proved that that he had the comedic chops to help carry a film.
2. Forgetting Sarah Marshall
Hill only has a small supporting role in this 2008 comedy, but it’s a memorable one. As Matthew, the starstuck waiter in the restaurant of a Hawaiian resort, Hill is at the base of several standout funny moments — usually as he’s desperately trying to get the attention of his idol Aldous Snow (Russell Brand).
Case in point? When Matthew eagerly asks Aldous to listen to his demo, it leads the latter to deliver one of the most quotable lines of the movie: “No, I was gonna listen to that, but then, um, I just carried on living my life.” The hilarious give-and-take between the two actors later led to the Forgetting Sarah Marshall spinoff Get Him to the Greek.
Hill dipped his toes into more dramatic fare with this 2010 dark comedy from the Duplass brothers. The actor displayed new facets as the two-faced, openly hostile, and disturbingly clingy 21-year-old titular character. Under Hill’s silent, deadpan stare, Cyrus’s creepiness comes all too vividly to life, causing the film to strike a notable balance between humorously uncomfortable and borderline horror movie-like. Bolstered by great performances from Marisa Tomei and John C. Reilly, the flick proved that Hill can do serious and suspenseful just as well as he can do comedy.
4. Get Him to the Greek
Hill reunites with Brand’s Aldous Snow character in this 2010 comedy, in which he stars as a low-level record company executive assigned to escort a wild rock star to a high-profile comeback concert. Hill’s sheepish demeanor and passive tendencies make him the perfect foil to Brand’s over-the-top recklessness. The movie went on to earn widely positive critical reviews thanks to Hill’s winning performance and the hilarious dynamic between him and Brand.
Hill took both critics and audiences by surprise with his standout portrayal of Peter Brand, a young Yale grad with an economics degree who is also a student of sabermetrics pioneer Bill James. Though the 2011 film marked a radical departure from the Judd Apatow stoner comedies that moviegoers were used to seeing Hill frequent at the time, the actor aced the transition, proving he could hold his own among Hollywood vets like Brad Pitt.
“Hill has never been better than against Pitt’s rapid-fire machismo,” New York Magazine wrote of the movie, while Rolling Stone called his portrayal a “no-joke knockout.” Hill earned his first Oscar nomination for the role, in the category of Best Supporting Actor.
6. 21 Jump Street
The 2012 satirical action comedy earned overwhelmingly — and surprisingly — positive reviews, largely due to Hill and co-star Channing Tatum’s unparalleled chemistry. Though both actors earned praise for fully embracing the stereotypes their characters embodied, the movie continued a winning streak for Hill, who was just coming off his first Oscar nod at the time. In addition to once again showing off his impressive comedic timing with his performance, the actor also helped develop the story and served as one of the executive producers on the movie.
The 2014 follow-up was, in a rare occurrence, just as well-received as the original film, bringing a hilarious self-awareness to Hollywood’s long history of unnecessary sequels. The movie also marked a huge commercial hit for Hill, earning $330.5 million at the worldwide box office.
7. Wolf of Wall Street
Hill earned his second Best Supporting Actor Oscar nomination for his role as Jordan Belfort’s business partner and friend Donnie Azoff in this 2013 biographical black comedy. The actor’s portrayal earned high critical praise, more than holding his own against one of Leonardo DiCaprio’s biggest performances to date. As The Hollywood Reporter described, Hill’s “timing is terrific and he keeps offering surprises and nuances to the end.”
In addition to being a critical success, the film was a huge success at the box office, grossing more than $392 million worldwide during its original theatrical run and becoming director Martin Scorsese’s highest-grossing movie to date.