As a three-time Tony Award winner and recent recipient of the special 2024 Tony Award for lifetime achievement, Jack O’Brien is back where he belongs: the theater. O’Brien is at the helm of one of this season’s most anticipated plays, the two-hander The Roommate, starring icons Mia Farrow and Patti LuPone. In the play by Jen Silverman, Farrow and LuPone play an odd couple of sorts who meet when Farrow’s character seeks out a housemate to help with the bills. Entertainment journalist from Spectrum News NY1 Frank DiLella recently caught up with O’Brien to discuss working with such entertainment luminaries, and more.

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Jack, you’re working with two entertainment legends: Mia Farrow and Patti LuPone. Tell me about the first time you met up to work on The Roommate.

The first day we met was quasi-social. We all live in Connecticut, very close to each other. And I suggested we all meet. The whole play connected when I sat in my living room, looked in my kitchen, saw the counter, and thought, “That’s where the play takes place.” So I thought I would have the ladies come over, just sit on the couch, and read the play. And they were willing to do that. And I had not been in a room with both of them together — ever. Patti and I had not been in a rehearsal room together in 50 years.

What were you and Patti doing 50 years ago?

I did the first thing she did, which was The Acting Company. We did a production of The Time of Your Life and she played Kitty Duvall.

How did this project start to come together?

[Producer] Chris Harper — we had worked together before. When I did Hairspray in London, Chris was doing publicity. We’ve been acquaintances for a long time and especially with his association with Marianne Elliott, because she and I are very good friends. Chris called me up and said there’s this play called The Roommate, and I said send it to me. I didn’t know anything about it and I flipped over it. And it was one of those moments where I thought, “Oh, I know how to do this!” And we went back and forth about casting — What about this one? What about that one? We had a lot of crazy ideas. We really didn’t make any calls. The play originally had the women in their forties, and I said, “I don’t know about you, but I’m 85 now and that’s not a number I would’ve ever associated with me ever.” So, it’s a different thing going on and life is longer and people get lonely. I have a half a dozen of my best friends in the world — Marsha Mason, Stockard Channing, Swoosie Kurtz. And all those women — no one is writing plays for these people. So I suggested why don’t we up the ante a little bit, and that’s how we got Mia and Patti.

This is Mia’s first real Broadway role since 1979. She did appear on Broadway in Love Letters in 2014, but she was part of a rotating cast and sat on stage reading from the script. This is a big deal having Mia back on the boards.

She’s unbelievable. And to be perfectly honest, I didn’t want to compromise her or embarrass her. I did say to Mia and Patti, “I want you off-book by the first day because I want this not to be about an acting exercise but about a relationship.” And Patti was doing her concert, and she is fresh anyway because she’s never not working. But then there was Mia in the woods after all of this time. And I honestly didn’t know. But Jeramiah, my assistant, and Marsha Mason, my beloved associate director, I put them both on Mia. They worked with her. Cued her. And would come back to me and say she’s perfect with her scenes. And I thought this is astonishing. Mia found that muscle and made it happen. Her ability to get comfortable on the stage took some time because she’s used to hitting her mark. She’s used to doing another take. The interesting thing about her is that she cannot mark. She starts to say her lines and she’s in the play. She and Patti have this bond that is unlike anything I’ve ever experienced.

What’s your favorite Mia role? What’s your favorite Patti role?

For Mia, how could you not remember Rosemary’s Baby? I’m a rep director and Patti came from a rep tradition at Juilliard. When I think of Patti over the years, none of the performances that’s she’s been decorated for look like any other. One of my favorite moments is when she did Gypsy. There’s a moment when Mama Rose is pushing the kids around and she pushes the farm animal cutouts on stage. And Patti, because she’s also a clown — she’s hilariously funny — she did a look to the audience and I almost thought I was going to wet my pants, I laughed so hard. There are very few people who can do that.

Most people don’t know this, but you actually worked with Mia Farrow in the short-lived Broadway play Getting Away With Murder by Stephen Sondheim and George Furth.  

We only ran 17 performances, Frank! [Laughs.] That was the first time I ever met Mia. She and Stephen Sondheim were very close. She did an answering message, “a call-in,” as a favor to him. We recorded her in the studio — she came in in Levi’s and a T-shirt, she looked like she was about 18 — and she was dancing around and funny as hell. And then she came up with this idea: She said, “I want to do it as if I have a cold.” I thought, OK. And she was perfect. She tossed it off and I thought, “To be that comfortable as a creative person means you’re in that fever all the time.” And I think that’s true.

Patti LuPone is truly one of the greatest stage actors ever. She is the ultimate, in my book. You got to meet her way back when. Did you know 50 years ago when you first met her that she was a star?

Yes. John Houseman took me to Juilliard and let me direct and had me work with The Acting Company. Even back then in Group 1 at Juilliard she stood out.

You received a special Tony for lifetime achievement this past year. So deserving, Jack. What went through your mind when you got the call that you were going to be honored for your contribution to American theater? 

I was quite stunned. I was very moved. I loved that it was George C. Wolfe and me together. I thought that was significant and important because we are contemporaries.

In your acceptance speech, you said a life in the theater is a calling. When did you receive your calling?

I witnessed it from my twenties on. I was in rooms with Rosemary Harris and Ellis Rabb and Uta Hagen and Tammy Grimes and Brian Bedford. I was on that edge my entire life. I watched people who were committed with passion and had pride in what they did.

You’re always working. What’s next for Jack O’Brien now that The Roommate is up and running?

When I finish this, I start with the national company of Shucked. Then I go to London to cast the British version of Shucked, which will be done next summer in Regent’s Park. Then I go to Lincoln Center to do Ghosts as my farewell to Andre Bishop and his regime. And then we’re hoping to revive Hairspray on Broadway next summer. And then another tour of The Sound of Music will go out.