Jack O’Brien Has Stories About Everyone on Broadway

The Comeback’s secret weapon is a four-time Tony Award winner who isn’t afraid to name-drop.

Jack O’Brien hasn’t been sitting at Nice Matin on the Upper West Side for long before he pulls out his iPhone to read aloud the boldface names of every person he talked to at Tom Stoppard’s funeral last year. He also listed off those he saw at a distance but didn’t get a chance to speak to, such as Mick Jagger. 

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

O’Brien, 86, is a gleeful raconteur who has worked as a director in the theater since the 1960s, picking up four Tony Awards along the way, including for Hairspray, and has enough anecdotes to fill at least two memoirs. He was the American entrusted with major productions of Stoppard plays such as The Invention of Love and The Coast of Utopia, a three-part epic for which O’Brien won his third Tony. “I have not recovered from his death,” he says, biting into his French toast and doing bits with the waitress, who keeps coming back to check if we have enough coffee. “I had the best of it. As they say in The Heiress, I was taught by masters.”

A death, as it happens, led O’Brien to an unexpected late-in-life foray into television despite almost no acting credits, certainly not onscreen. In the third season of The Comeback, he plays Tommy Tomlin, sitcom star Valerie Cherish’s new hairdresser; Robert Michael Morris, who played her friend and hairdresser Mickey in the first two seasons, died in 2017. The show’s co-creators, Lisa Kudrow, who plays Valerie, and Michael Patrick King, cast O’Brien after they caught a YouTube interview he did with Playbill reminiscing about his career while promoting The Roommate, the play he was directing starring Patti LuPone and Mia Farrow (who live near him in Connecticut). “I’ll do whatever anybody says,” he says. “I talked for 50 fucking minutes.” King, getting in touch by way of mutual friend Victor Garber, asked O’Brien if he’d ever thought about acting. “I said, ‘Does the phrase bucket list mean anything to you?’” O’Brien recalls. “I’m at the point right now in my life where I just say ‘yes’ to everything.”

The Comeback is an abrasive comedy — O’Brien’s a fan, but “it makes a lot of people very uncomfortable; the word cringe comes up” — about Valerie’s attempts to make it back to relevance in a cruel industry. It premiered on HBO in 2005, taking on the relatively new universe of reality TV. Then it got canceled, developed a cult following, returned in 2014, and is now back nearly 12 years later for a season, supposedly its last, in which Valerie ends up on an AI-written sitcom titled How’s That?! She needs someone to do her hair and runs into Tommy while filming a no-budget indie at the retirement home where he lives. Like O’Brien, Tommy is puckish and up for anything, especially a good gag. On his first day on set, Tommy pulls off a hat to reveal a bright-red hairpiece. “If anybody asks,” he deadpans, “I’m 70.” “It’s adorable,” O’Brien says. “And they based that wig on Robert Redford!”

The part of Tommy wasn’t written as a replica of Mickey, and O’Brien plays him accordingly. He’s less gentle than his predecessor, more direct. 

In the show’s third episode, which acts as a tribute to Morris, Tommy and Valerie butt heads as she works through her sense of loss and her frustration that he doesn’t have the exact wig she wants. “I’m her truth-teller, which is a very different kind of support system, and that’s basically what I do in life,” O’Brien says. Tommy’s honesty is something like a director’s honesty. “I’ve sat in front of some of the greatest actors we’ve produced over 60 years,” he says, “and it’s not that you can learn it from osmosis, but you can recognize it when you see it. You can say, ‘That’s the truth.’” 

O’Brien got his start in the theater writing full-length musicals at the University of Michigan and fooled around with skits for his fraternity but gave up acting mostly — he gestures to his skull — because he started going bald at 22. (He tried a hairpiece once, and it slipped out of place in front of Helen Hayes at a pool party. “I saw Ms. Hayes go” — he mimes a giant gasp. “I went off to the bathroom, saw myself in the mirror, and said, ‘Jack, this isn’t who you are.’”) After graduating, he worked for Ellis Rabb and Rosemary Harris’s famed APA repertory company and directed a calling-card revival of Porgy and Bess in 1976. He has moved from project to project ever since, dipping back into acting only when absolutely necessary. In 1990, while running the Old Globe theater in San Diego, he filled in during a run of Love Letters when nobody wanted to work the week of Thanksgiving. He recalls Michael Learned, his co-star, asking him to cry at the end of the play. “On opening night, I cried and everything,” he says. “But then, the minute I thought I’m good at this, I couldn’t do it again. Which is why I can’t watch the rest of The Comeback.”

As a director, O’Brien has followed a path that’s intentionally difficult to summarize. He’s not one to leave a trademark, nor does he cultivate a sense of auteurist mystery, which means, he jokes, he’s not interesting enough to make good copy. (Talk to Joe Mantello instead, he suggests, referring to the director of Wicked on Broadway: “He’s got to be the richest person, so he doesn’t have to work.”) But it is possible to point to a few key threads.

O’Brien’s a go-to for coaching unselfconscious comedy from a performance — in Hairspray, he told his actors to write you’re not funny, it is on their makeup mirrors so they’d trust the script. With Stoppard, he aimed at unself-consciousness, too, or at least a little heat. “I found him one of the most seductive human beings I’d ever known,” O’Brien says. (He tries to imitate Stoppard’s stentorian way of giving notes, then says he can’t do the accent; he tells me Ethan Hawke, one of the stars of Utopia, could do it better.) “And I thought, Where is that on the page? Brits love that intellectual tilting,” he says. “Americans have to feel something to be engaged or we think it’s fake. So I concentrated on putting that part of him into the work.”

O’Brien is enjoying his brush with a new medium, if ambivalent about keeping it up. He compares his star turn to John Houseman’s, another director who helped O’Brien’s career early on and who ended up in front of the camera in The Paper Chase in 1973. But O’Brien makes it clear he is not about to turn Hollywood full time. He has his gripes about the long days of filming television and repeating tongue twisters for the camera, like “I did guest-cast hair for I’m It!,” which was Tommy’s job on Valerie’s ’80s sitcom.

And anyway, he’s got more Broadway left in him. Recently free of the cane he was using after an ankle injury on Marsha Mason’s porch, he’s working on three plays as well as a musical and is in talks about a 25th-anniversary revival of Hairspray next year. He’s also still spreading the word about his last Broadway outing, Shucked, which got nominated for nine Tony Awards in 2023 and is now touring.

At Nice Matin, O’Brien wears a hat that reads get shucked. He notes we’re sitting across from the booth where he used to catch up with John Lithgow and wonders how his turn in screen acting will be received on Broadway. So far, the reviews seems positive, “so I have to say I guess it’s okay.” But it’s hard to predict the later notices. “You know, actors will tell you” if they have notes, he says. “Particularly if you’re a director, actors will tell you.”

Thank you for subscribing and supporting our journalism. If you prefer to read in print, you can also find this article in the April 6, 2026, issue of New York Magazine.

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