Hill then made a brief appearance in Judd Apatow’s directorial debut The 40-Year-Old Virgin, which eventually led to him appearing in the role of a virgin video game tester in the comedy Grandma’s Boy (2006) and starring in a larger supporting role in the Apatow-directed Knocked Up (2007). On television, Hill played the “RA Guy” on the first season of the Oxygen Network sitcom Campus Ladies. He guest-starred in an episode of Clark and Michael.
His first leading role was in the Apatow-produced comedy Superbad. Hill starred in the film alongside Michael Cera, in roles based on the film’s writers, Seth Rogen and Evan Goldberg. The film is often cited as the film that launched the careers of the two actors. He followed it with an uncredited role as Dewey Cox’s grown-up brother, Nate Cox, in Walk Hard: The Dewey Cox Story in December 2007. He was scheduled to host Saturday Night Live on November 17, 2007, which would have featured musical guest Kid Rock, but the episode was canceled due to the Writers Guild of America strike, which took place between November 5, 2007 and February 12, 2008. Instead, he hosted the March 15, 2008, show, which featured musical guest Mariah Carey (who replaced the originally scheduled musical guest Janet Jackson).
He turned down a role as one of the three principle comedic actors in the The Hangover so he could work with directors Jay Duplass and Mark Duplass in Cyrus (2010). Hill was in negotiations for a part in Transformers: Revenge of the Fallen as Sam Witwicky’s sidekick, but this did not go through. He guest-starred in an episode of Reno 911!, which aired on April 1, 2009.
He next starred in Judd Apatow’s third directorial feature, Funny People (2009), which also starred Adam Sandler, Eric Bana and Seth Rogen. He was an associate producer of the 2009 Sacha Baron Cohen mockumentary Brüno. He guest starred on an episode of The Simpsons called “Pranks and Greens”, portraying an immature man named Andy Hamilton who was hailed the best prankster in Springfield Elementary School history.
In July 2011, Hill appeared at ESPN’s ESPY awards sporting a much slimmer physique. He stated he had lost 40 pounds. In November 2011, Hill, along with Sam Worthington and Dwight Howard, starred in commercials for the video game Call of Duty: Modern Warfare 3, making his first appearance with his new look.
Also in 2011, Hill, alongside Andrew Mogel and Jarrad Paul, created Allen Gregory, a cartoon series that received widely largely negative reviews and was officially cancelled by Fox on January 8, 2012.
Hill received a Golden Globe nomination, his first nomination, for Best Performance by an Actor in a Supporting Role in a Motion Picture for his performance in the 2011 sports film Moneyball, in which he portrayed his first dramatic role as Peter Brand. In late January 2012, Hill received his first Oscar nomination for Best Actor in a Supporting Role for his role in Moneyball. In 2012, Hill co-starred with Channing Tatum in the film 21 Jump Street, and with Ben Stiller and Vince Vaughn in the film The Watch. In 2011, it was announced that Hill was in talks to appear in Quentin Tarantino’s film Django Unchained. Hill almost had to decline a possible role due to his prior commitment to The Watch, lamenting that to act in a Tarantino movie was “the perfect next step” in his career. Hill later rejoined Django Unchained, which was released in 2012. He was invited to join the Academy of Motion Picture Arts and Sciences in June 2012 along with 175 other individuals.
In 2013, Hill appeared in This is the End as himself and the biographical film The Wolf of Wall Street. Hill was nominated for his second Academy Award for his work in the latter film. In an interview with Howard Stern on January 21, 2014, Hill said he earned US$60,000 for his role in The Wolf of Wall Street because Hill took SAG’s “minimum wage”. Hill told Stern he did not mind getting minimum pay because he “would have done anything in the world” for a role in a Scorsese film.
He voiced the Green Lantern in the adventure comedy The Lego Movie in February 2014, which blends computer animation and live action. Hill reprised his role as Morton Schmidt in 22 Jump Street (2014), the sequel to 21 Jump Street. His next performance was as Michael Finkel in True Story (2015), a mystery thriller, alongside James Franco. In 2016, he played a surety agent for a production company in the Coen brothers’ period comedy Hail, Caesar! and starred alongside Miles Teller in the biographical crime war comedy-drama War Dogs, playing arms dealer Efraim Diveroli, in August 2016. In The Guardian, Wendy Ide wrote of his performance, “Jonah Hill is so repellent – all swagger, sweat and unapologetic sexism – in War Dogs, that for a while, you don’t immediately realise what a blitzkrieg of a performance he delivers.” Hill also co-starred as sausage named Carl in adult computer-animated comedy film Sausage Party, alongside Seth Rogen, Kristen Wiig, Bill Hader, Michael Cera, and James Franco, in the same month.