MAMA'S BOY: Though Hill claims to have "the best mom in the world," he competed with John C. Reilly (right) for the affections of on-screen mom, Marisa Tomei (center), in the film Cyrus.
Everett Collection

Though only 23 at the time, Hill was mindful that his newfound currency could be easily squandered, should he succumb to playing again and again the lovable, foul-mouthed teenage outsider. Instead of cashing quick paychecks for the next round of youth romps, Hill yearned for diversity and longevity, seeking out projects that would demonstrate his acting chops and range — and hopefully extend a lucky break into an actual career.

Hill found his perfect match in 2010’s Cyrus, a low-budget indie film from Mark and Jay Duplass, in which the actor plays an Oedipal mess tormented by his single mother’s deepening attraction to a new boyfriend. The performance reveals a temperamental and tonal collision, at once harrowing and hilarious, that marks Hill’s finest work. Mark Duplass, who co-wrote and co-directed the film, says, “Jonah has an innate interest in and understanding of the human condition. He understood that the character of Cyrus was simultaneously sad, funny and terrifying.”

For Hill, the role — more dramatic than the fare for which he’d become famous overnight — was exactly what he’d been looking for. “I love when you can sort of straddle that line between terror and hilarity,” he says. “That’s why Martin Scorsese is my favorite filmmaker, because there’s a real danger to his movies. It gets really dark and then it gets really funny and then it gets really dark again. To me, the best movies are all of those things in one. It doesn’t have to be so separate, like, ‘This is a serious movie, and this is a funny movie.’ Life’s not like that.”

Cyrus paved the way for Moneyball, in which Hill gave a sly, understated, Oscar-nominated performance as a baseball number cruncher, which in turn led to his Wolf of Wall Street audition. Hill was ecstatic at the opportunity but revealed it to no one, figuring the job would go to another actor.

On the day of the meeting with Scorsese, Hill — who hadn’t auditioned for a film in six years — was incredibly nervous. The pair met in Scorsese’s New York screening room, where the air conditioner had recently conked out, leaving Hill an “anxious, sweaty mess,” he recalls. “I was just thinking, ‘Oh, this is going to be a disaster.’ ”

Moving the audition to Scorsese’s much-cooler office, they punched through a number of scenes together. The actor relished every last moment. “I walked all the way back to my hotel in New York — like, 70 blocks — just feeling like this is the most amazing experience in my life,” he says. “I never expected to get the part, and if it had ended there, I was still the luckiest guy in the world.”