Jack O’Brien Has Stories About Everyone on Broadway

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It doesn’t take long for Jack O’Brien, while at Nice Matin on the Upper West Side, to start scrolling through his iPhone and reciting the names of everyone he chatted with at Tom Stoppard’s funeral. He even mentioned people he spotted in the crowd but didn’t get to speak to, like Mick Jagger.

“You can’t believe the people who were there,” he says.

At 86, John O’Brien is a lively storyteller with a long career in theater, starting in the 1960s. He’s won four Tony Awards, including one for the hit musical Hairspray, and has countless stories to tell. He directed major American productions of plays by Tom Stoppard, like The Invention of Love and the three-part The Coast of Utopia, which earned him his third Tony. Speaking while enjoying breakfast, he fondly remembers a mentor who recently passed away. “I was incredibly lucky to learn from the best,” he says, referencing a line from the play The Heiress.

An unexpected opportunity arose for O’Brien to appear on television later in life, despite having virtually no acting experience. He joined the third season of The Comeback as Tommy Tomlin, the new hairdresser for Valerie Cherish, after the actor who previously played the role, Robert Michael Morris, passed away in 2017. The show’s creators, Lisa Kudrow and Michael Patrick King, discovered O’Brien through a YouTube interview he did with Playbill. In the interview, he discussed his career while promoting The Roommate, a play he was directing with Patti LuPone and Mia Farrow (who are his neighbors in Connecticut). O’Brien says he was happy to do anything asked of him, and the interview lasted nearly an hour. King, reaching out through a friend named Victor Garber, asked O’Brien if he’d ever considered acting. O’Brien jokingly responded that it was something on his “bucket list.” He explained that he’s at a point in his life where he simply says “yes” to every opportunity.

The comedy series The Comeback is known for being intentionally awkward – many viewers find it uncomfortable, but creator Lisa Kudrow is a fan. The show follows Valerie, an actress trying to revive her career in the cutthroat world of television. It originally aired on HBO in 2005, satirizing the then-emerging genre of reality TV. After being canceled, it gained a dedicated following and was revived in 2014. Now, almost twelve years later, it’s back for what’s billed as its final season. In this season, Valerie finds herself starring in a sitcom written by artificial intelligence called How’s That?! While filming a low-budget movie at a retirement home, she reconnects with Tommy, a playful and adventurous resident. Tommy, like Kudrow, loves a good joke. On his first day on set, he jokingly reveals a bright red wig, deadpanning, “If anyone asks, I’m 70.” Kudrow describes the wig as “adorable,” adding that it was modeled after one worn by Robert Redford!

Tommy’s character wasn’t meant to be a copy of Mickey, and the actor, O’Brien, portrays him that way. He plays Tommy as more straightforward and less soft-spoken than the previous actor’s portrayal of Mickey.

The third episode of the show honors Morris and features a conflict between Tommy and Valerie. She’s struggling with grief and upset that the wig she requested isn’t quite right. According to O’Brien, Tommy serves as a voice of truth for her, offering a unique kind of support that reflects his role in life. Tommy describes his honesty as similar to that of a director – he’s spent decades working with talented actors and can identify genuine truth when he sees it. He explains that while honesty can’t be taught, it’s immediately recognizable. He knows it when he sees ‘the truth’ in someone’s performance.

Jack O’Brien began his career writing musicals at the University of Michigan and doing comedy with his fraternity. He stopped acting early, around age 22, when he started losing his hair. He recounts a particularly embarrassing moment when a hairpiece slipped off in front of the legendary Helen Hayes, leading him to realize it wasn’t authentic to who he was. After college, he worked with the APA Repertory Company and in 1976, directed a revival of Porgy and Bess. He’s been moving between projects ever since, only acting when unavoidable. While managing the Old Globe theater in San Diego in 1990, he stepped in to perform in Love Letters during Thanksgiving week when no one else was available. His co-star, Michael Learned, even asked him to cry during the final scene. He managed it on opening night, but once he started thinking about performing the emotion, he couldn’t do it again. This is why he finds it difficult to watch himself in the show The Comeback.

O’Brien’s career as a director hasn’t followed a typical, easily defined route. He deliberately avoids developing a signature style or an air of artistic mystery, playfully suggesting he isn’t captivating enough for a compelling story. (He recommends speaking with Joe Mantello, the director of Broadway’s Wicked, joking that Mantello’s success means he doesn’t need to work.) Despite this, some common themes do emerge when looking at O’Brien’s work.

I’ve always admired how director John O’Brien unlocks truly natural comedy in his actors. He has this fantastic technique – for Hairspray, he had everyone write ‘you’re not funny, it is’ on their makeup mirrors to encourage them to just trust the material. He tried to achieve that same unselfconsciousness with Tom Stoppard, or at least bring some of that energy to the surface. He describes Stoppard as incredibly charismatic – almost seductive, actually. He even tried to mimic how Stoppard would deliver notes, though he admitted he couldn’t quite nail the accent (apparently Ethan Hawke is much better at it!). What O’Brien realized was that Stoppard’s intellectual playfulness resonated deeply with British audiences, but to connect with American viewers, they needed an emotional core. So, he focused on infusing that compelling side of Stoppard into the work, making it relatable and engaging for everyone.

O’Brien is having fun trying acting, though he’s not sure if he’ll continue. He draws a parallel to John Houseman, who also helped launch O’Brien’s career and later starred in the 1973 film The Paper Chase. However, O’Brien insists he doesn’t plan to become a full-time Hollywood actor. He finds the long filming days and repetitive lines tiresome – he jokingly mentions having to say things like “I did guest-cast hair for I’m It!,” a line Tommy delivered on Valerie’s 1980s sitcom.

He’s not slowing down anytime soon! Recovered from an ankle injury, he’s currently involved with three plays and a musical. There’s even talk of bringing back Hairspray for a 25th-anniversary production next year. Plus, he’s still promoting Shucked, which received nine Tony Award nominations in 2023 and is now traveling the country on tour.

At the Nice Matin restaurant, O’Brien is wearing a hat that says “get shucked.” He points out they’re sitting at the booth where he used to chat with John Lithgow and is curious how audiences will react to his own acting performance on Broadway. Early reviews look promising – “so I guess it’s okay,” he says – but it’s difficult to know what later critics will think. “Actors will let you know if they have feedback,” he explains, “especially if you’re the director.”

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2026-04-06 14:55