In Always Great, Awards Insider speaks with Hollywood’s greatest undersung actors in career-spanning conversations. In this installment, Josh Charles looks back at his teen breakouts in Hairspray and The Dead Poets Society, through to his recent acclaimed work in We Own This City and The Veil.
When Josh Charles first got a call from his old friend Ethan Hawke about appearing in a Taylor Swift music video, he assumed it was a prank. “I thought, Am I getting punked here?” Charles recalls. “But Ethan’s not the kind of guy that would punk me. He’s just not that dude.” Indeed, Hawke was serious—as was Swift, about having the two veteran actors reprise their breakout characters from 1989’s The Dead Poets Society for the flagship single from her new album, The Tortured Poets Department. It’s about as unusual as full-circle moments get in this business.
“Ethan and I just were like, How can we not do this?” Charles says. “It’s kind of amazing to see a film that you made so long ago still affecting so many people.”
Charles likes to take these moments in. He comes to our decades-spanning conversation ready to discuss high points as well as regrets. He’s been a working actor since childhood, and often finds himself fighting his industry’s worst tendencies. But then comes something like that video, or his a juicy supporting turn in a FX’s The Veil (now streaming on Hulu).
Charles portrays a CIA officer named Max, who’s both chasing and collaborating with Elisabeth Moss’s MI6 agent Imogen as she unravels an international conspiracy. The character is right in Charles’s wheelhouse: brashly charming, arrogant with some cause, commanding attention. “He’s a bit of, as they would say in Jungian terms, a trickster, and I dug that,” Charles says. “He fucks with things in a great way.” One could say the same thing about the man who plays Max.
Growing up in Baltimore, Charles idolized Richard Pryor and spent his childhood memorizing the comedian’s legendary routines. By 15 years old, he had secured a most auspicious—and local—debut movie role: Iggy, one of the teen council members in John Waters’s cult classic Hairspray. Charles didn’t feel any pressure on the set. “I got a lot of my own costumes for that from a vintage shop, and we did the dance rehearsals in my dad’s studio,” he says. “It was just very Baltimore.”
Then he auditioned for Dead Poets Society, a process that hardly felt so scrappy. He’d booked the key role of Knox Overstreet, a student at an all-boys prep school in Vermont, and felt its potential to change his life. Then development lagged, the original director Jeff Kanew left the project, and a week before Charles was supposed to fly to Georgia, the project was canceled, as far as he knew.
“I was devastated,” he says. “I just couldn’t get my head back into school because I was so ready to go and step into the world of which I saw would be my career.” A year later, Dead Poets was revived. Directed by Peter Weir, it became an Oscar-nominated Robin Williams vehicle. “We got to go to Venice and Italy and London and Japan and do press—I mean, things that an 18-year-old at that time just doesn’t get to do,” he says.
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Inevitably, a roadmap was laid out for Charles. As offers came in, he became acquainted with the machine that greets many young actors on the rise. “You realize very quickly that not a lot of movies are like” Dead Poets, says Charles. Some work still satisfied, like working with Alan Arkin in the TV film Cooperstown or playing a risqué gay twentysomething in the maligned 1994 erotic comedy Threesome. “I’m not saying it’s the greatest movie ever made, but it wasn’t a time when people were doing those types of roles, and I felt like that was me taking a leap into something,” Charles says. “Through the lens of today, it seems really dated, but at the time it wasn’t. And you know what? A lot of gay men have come up to me and talked about what that movie meant to them in their younger years.”
After the movie came out, Charles wasn’t getting many offers for characters that weren’t gay: “You sit there and go, What is wrong with people in this business? They can only literally think about what’s right in front of them.”
This push-and-pull defined Charles’s twenties. He wonders now if he was too picky, if he overthought everything, if he should’ve taken some time away when the noise was at its loudest. “I wish in a way that I wasn’t a child actor, because I would’ve liked to have had a college experience,” he says. “I don’t think I was always as conscious as I am now about things.”
Charles hadn’t done much TV before Sports Night came his way. Playing the lead in the first show from Aaron Sorkin, already a hot screenwriter by that point, seemed like a major step forward. But though the half-hour series was a critical hit, making it was not especially pleasant for the actor. (The show ran from 1998-2000.) “I’m really proud of some of the work in it, despite it not being the best experience for me creatively working with Aaron—and it wasn’t. I’m not going to lie about that. I really don’t give a shit,” Charles says. “It made me not want to do TV again because I thought, ‘Is that what TV is like, working with people like this? I don’t want to do that again.’” (He’d rather not elaborate, but does later say, “Sports Night wasn’t a collaboration—not the way I would like it as an actor.”)
Charles recalibrated by taking roles on stage, earning strong reviews for work off-Broadway in Neil LaBute’s The Distance From Here and Adam Bock’s The Receptionist. He also made a name for himself in the Steppenwolf company in Chicago, and collaborated with director Anna D. Shapiro on an experimental play called A Number in San Francisco. “I was terrified, but I tackled it and I remember the feeling of facing something shit-scared and just getting through it—like I redeemed myself in some way.”