"It derailed me for 16 years."

Hill's "amazing derailment" put him in front of the camera, where he went on to co-star in Superbad, Moneyball and The Wolf of Wall Street, among other films. But throughout it all, his desire to make films never subsided.

Now he's written and directed his first movie, Mid90s, which centers on a group of teenage skateboarders in '90s-era Los Angeles. The characters in the film display a mix of small-mindedness, prejudice and misogyny — as well as camaraderie and unexpected tenderness.

Hill says the film springs from his own experience as a teen skater: "[There's] just a general recklessness which I related to. ... Even though this isn't my story, I wanted to show someone going through deep pain and a real sense of hope through community."

Hill isn't sure how Mid90s will be received, but regardless, he feels lucky: "My goal my whole life was to be a writer and director. To say, 'This is a dream,' what's happening now, is like an understatement."


Interview Highlights

On taking a lot of risks with Mid90s

[I did] all the things they say you're not supposed to do: work with kids, work with first-time actors, take on a subculture that hates being talked about, mentioned or represented. ... So for me there's something about me that draws me to things that are difficult and maybe I'm uncomfortable with comfort and I think my acting career says that when I really dissect it, as well.

On portraying the way some kids spoke in the '90s, including using the word "gay" as a synonym for lame

That is something that a kid would have said to another kid. But how absurd and messed up is that? That that was the mentality or wasn't blinked at, when things like that were said back then. That was a choice I made, some of the language is really hard to watch for me, some of the actions are really hard to watch for me, but ultimately I felt it was more unfair to rewrite history than to show it as bluntly and as uncomfortable as it was.

And the difficulty of watching it is deliberate at times. And also these young men are also very there for one another. And my point is that things aren't so black and white. People can do horrible things and still do kind things. People can do kind things and still do horrible things.

On toxic masculinity and learning to express himself and show vulnerability

As I've grown up as a human being, and have had the emotional maturity and confidence to become a filmmaker, [I've reflected on] how I learned to communicate as a man and why that was problematic. ...

I was taught and maybe culturally we were taught at that time, if you're a man and you express your feelings or you express that something hurts you, then you should be made fun of. And that kind of repression leads to anger, and anger leads to bad behavior. And I think I wanted to show a film about young men with an inability to express themselves. And in my life, it's been a real joy being able to blossom and to feel free and comfortable in my own skin enough to express myself.

On reflecting on a line his teenage character says in Superbad about wanting to "be that mistake" — wanting to be the man a woman regrets having sex with

This young man is hoping the young woman is so inebriated that her judgment would be so poor that she would make a mistake by sleeping with him. And that is incredibly wrong. ...

Comedy has a really hard time in the aging process, because things that are funny at a moment or people might laugh at, as times change. ... For some reason it was OK to make a joke about [taking advantage of drunk teenage girls] at that point, whereas of course it's not. ...

I was 23 — not that that's an excuse, but I don't think I had the emotional maturity to understand that those words, or that joke, would be so horrible, because that's the reality. I don't think I ever thought of that as a reality, because it's not my experience, and so now thinking of that as a reality is very hard to hear.

I literally can only speak for myself as an actor in that moment. I didn't see how hard that is and how ugly that joke is. But I don't want to speak for the filmmakers, because this is such a larger, hard issue where a 13-year-old joke stands now. When I hear that, it's very disturbing. But I also know those people that wrote it, and they're really good people. So, it's just so complicated I never want to be hurtful to anybody, either side.

On something he learned from working with Martin Scorsese on The Wolf of Wall Street

I guess the main lesson I learned was that it's OK not to judge your characters, to just show their behavior as people. And the characters in his films often do really ugly things and you still find humanity in them. I like how unabashedly and unapologetically he shows human behavior, for better or worse. ... Which is, I think, something that really speaks to me in art in general and something I'm going to strive to do if I'm lucky enough to get to make another film, and something that I tried to do in Mid90s.

Lauren Krenzel and Thea Chaloner produced and edited this interview for broadcast. Bridget Bentz, Molly Seavy-Nesper and Beth Novey adapted it for the Web.

Copyright 2018 Fresh Air. To see more, visit Fresh Air.

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