Jonah Hill is in a moment of reinvention. At least, that’s what people keep telling him, usually with an eyebrow raised, as though his evolution from schlubby comedy star to sensitive indie director might be just another joke. It’s been more than a decade since Hill became famous as Superbad’s X-rated doodler, a fast-talking clown voted Most Likely to Get Hit by a Cop Car. Since then, he’s earned two best supporting Oscar nominations (for Moneyball and The Wolf of Wall Street) and yet audiences still seem to approach his serious roles tentatively, as though he might pop out and splat a pie in their face. The question isn’t just: is it time to take him seriously, it’s why is taking him seriously so hard?

“Anyone who knew me was very surprised that this first half of my life went the way it did,” says Hill on a recent afternoon in Beverly Hills. “My dream was always to be a filmmaker.” He’s dressed in a sweater and horn-rimmed glasses with just a pop of whimsy: the sweater is mauve and his hair is streaked platinum blonde.

Hill grew up pasting pictures of Stanley Kubrick and Martin Scorsese on his bedroom walls. His upper middle-class Los Angeles childhood was entertainment-adjacent – Hill’s parents were on the fringes of fame. His mother Sharon was a costume designer and his father Richard was an accountant for Guns N’ Roses. “But it wasn’t like rock stars and shit,” says Hill. “Dealing with finances is not really that interesting.”

Yet they encouraged their kids to create. The family’s natural performer was his younger sister Beanie Feldstein, the breakout star of Lady Bird and the upcoming comedy Booksmart. “She’s built for it,” says Hill. “I want to direct her really badly.” His older brother Jordan, who died suddenly in 2017 from blood clots that originated in his legs, managed the band Maroon 5.

‘My dream was always to direct’: Jonah Hill on the set of Mid90s with actors Lucas Hedges and Sunny Suljic. Photograph: Tobin Yelland

When Hill was eight, his parents explained that real humans were responsible for his favourite cartoon, The Simpsons, and it changed his life. Some adults did the voices, they told him, and others wrote the dialogue.

“I was like: ‘I can’t believe that’s a job!’” exclaims Hill. And then he made a prophetic choice. Instead of wanting to imitate Bart and Homer, young Hill began to write Simpsons screenplays, and kept at it until he was 16, a monomania seen more often in pianists and Olympians. The show remains his biggest influence; he learned about Scorsese from the Cape Fear-themed episode where Sideshow Bob stalks Bart. Recently, he flipped through his old scripts. “I don’t think they’re going to win any Emmys,” he admits.

He became an actor by accident. Dustin Hoffman’s son Jake was Hill’s classmate at his Santa Monica private school. Hoffman surreptitiously watched Hill make crank calls pretending to be Tobey Maguire’s assistant – he once convinced a hotel to install a tank for Maguire’s fictional pet seal. Impressed with Hill’s ability to improvise, Hoffman invited him to audition for a small role in I Heart Huckabees. He got a taste for it. From there, Hill kept landing gigs, sometimes in movies he still hasn’t seen, like Adam Sandler’s Click. Soon, he was welcomed into Judd Apatow’s troupe and gifted the blabbermouth Superbad role Seth Rogen had written for himself – his character was even named Seth – and his public persona solidified into a hard-charging, crash-landing obsessive who would say anything for a laugh.

“It’s a sliver of who you are at that age, and you exploit it and everyone else exploits it,” says Hill. “All actors are typecast, but I tried to change whatever pigeonhole I was in because I didn’t want to get stuck there.” When you watch those earlier roles, the young actor is already committed to giving his characters moments of unusual depth. Even when he is the joke, he’s planted in the reality of the scene. In Superbad, his sexually frustrated high school student literally sobs. “I just have something in both of my eyes,” he whimpers to Emma Stone. “I don’t cry.”

‘All actors get typecast. But I didn’t want to get stuck’: as Donnie Azoff in 2013’s the Wolf of Wall Street. Photograph: Sportsphoto/Allstar

Today, as he discusses his directorial feature debut, Mid90s, a film about boys growing up, this joke still resonates. “Young boys don’t have the tools to communicate their sadness or pain,” says Hill. Recently, when an Instagram troll called him a fat nerd, Hill replied: “Anger is just sadness held in too long. I’m here for you dude.” The Superbad kid is attempting to model manhood. “Things like that aren’t traditionally masculine subjects to explore, but I’m learning that’s what I’m interested in in filmmaking.”

Mid90s is a rough ride over the bumps of burgeoning manhood. It’s the opposite kind of film to the one his Superbad fans might have expected he would make.

“Along the way I could have directed plenty of mainstream comedies, films that reflected the success of the early work I did as an actor,” says Hill. “But it is important that my first film did not let anybody’s ideas of what they thought I should be making define what I make.” As in, a big, loud, brightly lit comedy with a bunch of guys barrelling through the frame telling dumb, irresistible jokes.

Mid90s is a similar melody, but played in a minor key. It’s a period piece about a scrawny 13-year-old named Stevie (Sunny Suljic) who charms his way into a crew of older skateboarders. They introduce him to drugs, alcohol and sex, and the kind of brotherhood that is literally bruising. When one boy, an amateur skate videographer named Fourth Grade, admits he wants to make real movies some day, they mock his goals. The gang have each other’s backs, but they also hold each other back.

‘I was under pressure to do more comedy movies’: in 2010’s Cyrus with (from left) Marisa Tomei, John C Reilly and Catherine Keener. Photograph: Rex/Shutterstock

That same discouraging moment happened to Hill. When he was 11, he began to hang out with skateboarders, too, which means he has spent most of the press tour convincing critics the film wasn’t autobiographical, while also having to convince young men he had enough street cred to tell their story. One day, young Hill told his cooler, older friends that he hoped to direct. They just made fun of him.

“I remember that feeling of prising open a lid to express what I wanted to do and feeling so stupid immediately after. At the time I thought: ‘Oh, they’re right. I can’t do that.’ At that age everyone’s so insecure, and so you put people down because you’re like, if they can do their dream and I can’t, then I suck.”

“Acceptance wasn’t easy,” he admits. In a clique based on street cred, Hill stood out as a well-off Jewish kid who, frankly, could barely skate. “I would walk in there at 11 and get made fun of for being Jewish – it’s insane,” says Hill. “My currency was humour.” He learned to use jokes as a tool, even if the joke was calling himself Jonah the Jew. In a way, skateboarding has proven to be his through-line from the kid who loved to write Simpsons scripts to the 20-something Apatovian berserker to the 35-year-old filmmaker he is today. “Skating definitely broke me out of a religious bubble,” he says, “a socioeconomic bubble, a racial bubble.”

Super good: in 2007’s Superbad with Christopher Mintz-Plasse and Michael Cera. In its opening weekend, it took $31.2m. Photograph: Melissa Moseley/ASSOCIATED PRESS

It’s tempting to see Mid90s as a parable about self- reinvention that’s similar to what Hill is undergoing himself. Stevie is so desperate to find his own identity that he studies his older brother Ian’s (Lucas Hedges) Tribe Called Quest tapes as if they hold the secret to being a boy. After he ingratiates himself with his new friends, he takes down his dinosaur posters and replaces them with tear-outs from skating magazines. Yet Hill is quick to point out that he’s most drawn to Stevie’s ability to go all-in on his passions. “There’s something heartbreaking and awesome about it,” says Hill. Especially because skating – unlike Hollywood – celebrates failure. When Stevie falls and cracks open his skull, the others cheer.

“When I was, like, 11 or 12, I wanted to feel something,” says Hill. He started skating at the same age. “It says something about the person who’s willing to slam on concrete over and over again,” he notes. “Extreme pain – what kind of person does that attract?”

Someone willing to take big risks. Just like when Hill was so frustrated with his comedy typecasting that he made the most pivotal choice of his career: he said no to The Hangover, the massively lucrative franchise, and yes to a tiny indie movie named Cyrus, directed by Mark and Jay Duplass, that would re-align him with his serious ambitions.

“I was getting lots of pressure to do movies like The Hangover – and obviously I love The Hangover, it’s hilarious – but it was a no-brainer for me,” says Hill. “I’d never read a script as beautiful as Cyrus.” Hill played the title character, a menacing man-child who sabotages his mother Marisa Tomei’s budding relationship with John C Reilly. For the first time, critics started to see that Hill wasn’t just his generation’s loudest comic – he was, perhaps, a real actor.

That role gave him the ability to split his career into what, for a while, felt like cacophonous stereo tracks. In the same year, a Jonah Hill movie could mean anything, from the Academy Award-nominated Moneyball to the disastrous slapstick comedy The Sitter.

“Nothing is black and white,” says Hill. “As an actor, some moments I’m joking around and really silly; some moments I’m serious. If I deny that, then I’ll go crazy, because then I’m just playing a character.”

For now, Hill wants the right to be the whole rainbow. “I know I’m a director and that’s what I’m here to do,” he says. But he’s not finished with acting. Is he gunning for a third Oscar nomination? “The people I know who won Oscars, it didn’t change their inner peace at all,” says Hill. His next ambition is to be directed by a woman. Though it says less about him and more about who gets hired for big studio comedies and Oscar films. “It’s insane that my perspective as an actor has only been a male’s vision. And I didn’t make this movie to win Oscars!” laughs Hill of Mid90s.

He realises that audiences are just starting to accept who he’s always been. Fellow skateboarder-turned-director Spike Jonze even gave him an ego-check. “Spike said to me that I’m carrying the baggage of 15 years of people thinking they understand who I am as an actor – and I have to make a great movie to get to zero,” says Hill. “When he saw the film, he was like, ‘You’re at zero now.’”

Mid90s is on general release in UK cinemas next month