He's a four-time Tony Award winner who isn’t afraid to name-drop.
 

APRIL 6, 2026

 

ENCOUNTER

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.

By Jackson McHenry

Photo: Erika Goldring/Getty Images

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 Playbillreminiscing 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.”

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