From his early start in Judd Apatow films such as The 40-Year-Old Virgin and Knocked Up, and then his breakout role in Superbad, to his Oscar-nominated turns in Moneyball and The Wolf Of Wall Street, he has proved his chops as a funnyman and a dramatic actor.
But now he’s taken a different tack, one that has landed him in the director’s chair.
“This is what I wanted to do my whole life,” the 35-year-old says earnestly.
“I accidentally fell in love with acting and I definitely – probably – will act again, but this is what I always wanted.”
His debut, which he also wrote, is Mid90s, a nostalgic indie film about a 13-year-old boy living in Los Angeles in the 1990s, who spends his summer navigating between his troubled home life and a group of new friends he meets at a skate shop.
While many first time directors get to make their first film in relative obscurity, free to explore their learning curve away from too many prying eyes, Hill knew there would be particular attention paid to his.
“There is good and bad to everything, everything is multiple things. I wouldn’t have gotten to make this movie as purely as I did if I wasn’t a successful actor.
“It’s not a very pop, big, giant, subject matter and film – it’s a small emotional film, so I understand the rewards of that, but at the same time, people bring in all their judgements of my prior work to this film.
“I have a lot of great friends and mentors who are filmmakers and one of my closest is Spike Jonze [the director of Adaptation, Where The Wild Things Are and Her] and when he saw the cut of the film, he said: ‘This is a great film and you had to make a good film to get to zero. Now on your next film, you will be judged as a filmmaker.’
“So this just gets you to zero, because everyone is just thinking you’re an actor that has made a movie.
“But now this affords me to make my next movie, which is great, it’s all I ever wanted.
“Every director’s goal should just be: did your movie do well enough where they let you make another one?”
While Mid90s isn’t strictly autobiographical, the film is strongly reminiscent of Hill’s own childhood in Los Angeles.
“It’s not my story but definitely there are elements of things I went through,” he says, “and things that friends of mine went through.
“There are also things I completely made up, but as far as the tapestry of skate culture and a skate shop and going to skate spots with your friends, that was stuff I understood.
“And when you’re the younger kid, you’re working your way up through the animal kingdom. When you’re the older kid, you’re watching them struggle to work their way up in the animal kingdom.
“It’s an animal kingdom movie, essentially, a young cub going in and learning to survive and build himself within a pack.
“It would be an unfair portrait of growing up to not show the things that are heartbreaking or sad, as well as the things that are joyous and fun, [and] all the things that are just kind of boring everyday stuff.”
Hill settled on writing a story about childhood during a conversation with Jonze while they were writing a play together.
“After we would work on the play, we would talk about what we were writing, individually. And he and I would tell each other a story, which is a good writing exercise, having to tell the story from the beginning to end, over and over.
“I was writing my first movie. I tell him the story. And it was about something completely different.
“But it would flash back to when they were 12, skating, when the main character was skating with his friends.
“And Spike said: ‘You look really bored when you’re talking about the main story, and you light up when you talk about the flashbacks. You should just write that movie.’
“That was the moment I decided to start writing Mid90s and for four years, it’s been, like, whenever I’ve been lonely or had any excess energy – negative or positive – it’s gone towards this thing. It’s like my best friend.”
The next things Hill will be directing his energy towards, are music videos.
He has already shot one for the band Vampire Weekend and has projects with Gucci Mane and Travis Scott in the pipeline, too.
“Those are people that I really admire.
“I would love to work with Jay-Z, he’s someone who has been the best for so long and I admire a lot of the directors he works with on his videos, but Gucci and Travis are people I listen to every day in my car.”
Mid90s is released in UK cinemas tomorrow.