The 20 best Jonah Hill movies

It’s the classic tale of two BFFs determined to get rid of their V-cards before they go off to college. Hill and Michael Cera make an adorable pair of dweeby teens who just want to have one epic night before summer ends, and this movie is epic in its own right.

Hill plays the right-hand man to Leonardo DiCaprio’s Jordan Belfort, the real-life stockbroker turned felon who set 1990s Wall Street buzzing. Hill’s slightly timid, slightly sleazy Donnie Azoff steals a surprising number of scenes with this Oscar-nominated role.

Sports movies aren’t just about the big game anymore. They’ve become narratives of real human challenges and triumphs, and this true story featuring Brad Pitt, baseball’s Oakland Athletics and Hill in his first Oscar-nominated spot is no exception.

Hill proves to be surprisingly adept at dramatic portrayals, rolling with his stint as shamed and defamed journalist Michael Finkel, who takes it upon himself to peel back the dark and disturbing layers in a close-to-home case of stolen identity.

Paired with Channing Tatum’s equally unmotivated cop character, Hill plays a police officer with a knack for slacking in this reboot of the original 1987 TV series that sends the pair back to high school in an attempt to nab a surprisingly stealthy drug dealer.

Only Judd Apatow’s supervision could take this would-be tragic tale about mega-star Adam Sandler’s terminal illness to a place of poignancy and humor. Costars Leslie Mann and Seth Rogen join Hill in bringing about the bright spots.

As a resort worker in this comedy led by Jason Segel and Kristen Bell, Hill steals scenes as Matthew, the small-town waiter—and the No. 1 fan of Aldous Snow (Russell Brand)—with big showbiz goals and a demo to peddle.

Rejected from any and every opportunity for a traditional college education, a band of slackers (including Hill as Sherman Schrader III) finally pursue a goal in this easy comedy. They open up South Harmon Institute of Technology, a bastion for high school losers who might have something going for them yet.

A conceivable reality meets utter ridiculousness when actors step into caricaturistic roles of themselves, with the impending apocalypse thrown in for good measure. Watch this generation’s comedic band of brothers (including Hill, Rogen, James Franco and Jay Baruchel) survive the rapture in slapstick fashion.

In the 2014 sequel to 21 Jump Street, Hill and Tatum return—just like their characters are instructed—for the meta task of doing the same thing all over again, but on a college campus. One takes the hippy route while the other goes jock (surprise—it’s Hill!).