At 86, Jack O'Brien Is Starring on The Comeback—And It's Because of Playbill

Have you heard about HBO's hottest new actor? Why, it's none other than four-time Tony honoree Jack O'Brien, the director of such Broadway favorites as The Coast of Utopia, Hairspray, and Shucked. Yes, the esteemed Broadway director has gone to the other side of the curtain, and so far that he ended up outside the theatre, off the stage, and in front of a camera as hair stylist Tommy Tomlin in the much anticipated third season of Lisa Kudrow and Michael Patrick King's The Comeback, which premiered March 22 on HBO and is now streaming on HBO Max (new episodes premiere weekly on Sundays).

At first brush, it seems odd, or at least unexpected, to see a director suddenly getting an acting gig. But The Comeback has been anything but expected since it premiered in 2005. The show tracks a middle-aged former sitcom star named Valerie Cherish (played by Kudrow) who's working on a multi-camera sitcom and a reality show aimed at documenting her comeback, no matter how humiliating that might be. The show is something of an acquired taste—don't expect big punch lines. But its fans are many and tend to be quite passionate. That's why the show was initially cancelled after its first season, but then made an unlikely return for a second season a decade later, in 2014. A decade after that, the show is back for a third season, with Valerie now tackling another multi-camera sitcom, but one written by AI. The season opener is one for the theatre girlies as Valerie tries, and fails, to give 'em the old razzle dazzle in Chicago on Broadway.

If you're a Comeback fan, you can probably already correctly guess that O'Brien's character is a spiritual successor to Mickey Deane, played in the first two seasons by Robert Michael Morris, who passed away in 2017. Like O'Brien, Morris was not a professional actor when King asked him to play the role (another example of how The Comeback is anything but a traditional television series). Morris had been King's college acting professor, and the showrunner offered him the part as a thank-you for the years of mentorship and influence. The role turned the retired educator into a beloved acting figure. When he died in 2017, obituaries declared him a TV star.

And so, it's perhaps not surprising that when it was time to fill the hole left by Morris' absence, King and Kudrow stuck to the non-traditional casting; they reached out to O'Brien. But how did they find him? It wasn't from an audition.

"Well, it's all your fault!" O'Brien tells Playbill. Turns out that King, along with many of you, happened to catch O'Brien's episode of our My Life in the Theatre series, and realized the director's free-wheeling energy was perfect for The Comeback. "He called out of the blue. He got my number through Victor Garber," O'Brien says. "I just thought it is one of those things you just can't say no to. You can't—it'd be anti-life."

To find out more about O'Brien's journey becoming a screen actor at the age of 86, we caught up with the esteemed director. The conversation has been edited for length and clarity.

I know from your episode of My Life in the Theatre that your early career had a little acting, but how did that suddenly come back into your life?
Jack O’Brien: Well, it’s all your fault! I did that thing for Playbill, and with no thoughts in my head about it. The day we showed up to do it, I didn’t quite understand what I was doing. They put me in that little room with that little desk and the two cameras, and away I went. I must have talked for an hour. 

But Michael Patrick King—who is the creator of The Comeback, and Sex and the City, and a lot of other things—he saw this thing. He must have seen something in me that registered with him, not only as an artist, but as a fellow traveler. He called out of the blue. He got my number through Victor Garber. He said, “Have you ever thought about acting?” And I said, “Does the phrase ‘Bucket List’ mean anything to you?” I had acted in college, but then I lost my hair, which made me think what roles would I be playing? The only other time that I had to act at all was when I was running The Old Globe in San Diego. We had booked Love Letters through November, but no one would come down to the theatre during Thanksgiving week because they all wanted to be with their families. Someone said people would pay to see me, and I guess… well, I’d directed the production, and I figured there were probably a couple people I could get to do this with. One of them was Michael Learned, because we’d been really good friends. I called her and asked if she would do it with me, and she said, “Under one circumstance. You have to cry at the end. I’m dead, and if you don’t cry at the end, the audience won’t think you loved me.” 

And I did! It’s such a perfect script. If you follow it honestly, it leads you to a cliff and you just fall off. I wasn’t showing off. I was just serving the material. But I had no delusions about moving into acting. I was running a theatre, so I had no time to do that!

So had you been wanting to get back to that this whole time?
No. One of my many mentors was John Houseman. Late in his career, he got tapped by a former acolyte, Jimmy Bridges, who was doing a movie called The Paper Chase. James Mason had been cast, I think, and he suddenly couldn’t do it. Jimmy turned to his friend, his mentor, Houseman (who was running Juilliard at the time) and said, “Could you do this?” And Houseman said, “You must test me. I don’t think I can do this.” And of course, he won an Oscar for it. So that was kind of in my head when this call came in.

Were you familiar with The Comeback when Michael called.
Of course. I’m such a fan of [Lisa Kudrow’s]. I’ve been a fan of hers forever. When this happened, I just thought it is one of those things you just can’t say no to. You can’t—it’d be anti-life.

Tell me about your character!
He was a friend, a colleague of Mickey’s. Apparently I did guest star under him on her sitcom in the first couple years. When he went on vacation, I must have stepped in and helped her. That’s how it works. I had some cognizance as a character of what was going on, but my character doesn’t know that Mickey died. She tells me that. We hadn’t seen each other in years, and we weren’t that close, but I didn’t know that he died. My character is 85 years old. In fact, I’m 86, but I stretched myself down to do the part.

It must feel like a lot coming in essentially as the spiritual successor to a character that is truly so beloved.
Absolutely. You know, [the late Robert Michael Morris, who played Mickey on the show’s first two seasons] wasn’t an actor. He was Michael’s drama teacher. I thought that was so cool. Michael Patrick King is just the menschiest, most loving, most compassionate human being you could ever hope to find. He had cast him as a gift to this man that had made a huge difference in his life, and then he became kind of a star. When he died, he was referred to as a television star. Michael said that would have made him so happy, to know he had that effect on people. So I realized I had a sort of emotional obligation here, that I was carrying the proxy of a much beloved character, and I treated it that way.

Were you expected to re-create Mickey’s character as Robert Michael Morris played him?
No. From the beginning, it was clear I wasn’t being asked to either replace him or emulate him or act like him. It allowed me to just relax and be me. That’s what Michael wanted.

Did being you make you feel vulnerable at all, or was it just easy?
A little of both. I mean, please understand, Michael and Lisa, they wrote this for me. I wasn’t trying to be, you know, Pedro Pascal or somebody. The character is very much who I am, and so I was able to feel comfortable in my own skin and know that I wasn’t trying to be something I’m not. I just trusted their instincts, and I think I was able to do so well.

And what was it like becoming an actor—and not just acting, but also acting for the camera as opposed to the stage!
Well, it’s a lot of standing around. I’m not kidding, I think I had one day that my call was 5:15 AM and they delivered me back to the hotel at 8:30 PM. I was in every shot—and I only had four lines! People my age don’t stand for that long. I don’t know how I did it. I suddenly began to realize that I had a lot more energy, a hidden steel. It was helpful, because now over New Year’s, I broke my ankle. I fell on black ice and broke my ankle, so I’ve been in a cast and had an operation, and I’m just now getting off the cane. But for me to be inactive for that period of time was really complicated. But it’s been nice knowing what I was capable of, what I have the energy for. That was a great gift to me.

What new perspective or insight did the experience give you as you return to your normal directing career?
Well remember, we’re not in the same aisle. The film and television guys and women are very specific about what they need to get, what they need to achieve what they think they want to do. I’m in the business of putting heartbeat into a character, so they can sustain themselves on the stage. I don’t have to be as specific as a film and television person has to be in order to match in my head what we’re doing. Michael does. There were many times when he would say, “Say that again. Say it again.” 

It was terrifying, but kind of fabulous, because I felt what it was like to be on the other end of the spectrum, to reach into yourself and say, “I haven’t found it yet. How do I give this person who I really respect what they’re looking for?” That would never happen with me and an actor, because I don’t dictate. I try to give options. I try to illuminate. I try to solve, to unknot problems for them so they’re free to create themselves on stage. It’s not the same thing. And that was so helpful to know.

But was it strange not being in charge, to not have the final say?
The two of us were kindred spirits right from the get-go. I had such respect from him. I know something about how you create a company. It’s very important that you instill in the company their confidence and their generosity and their respect for each other. When that’s happening, you’re in the good shit. You’re in the good part of the spectrum. Michael does that. He was wonderfully supportive and encouraging, and I was deeply insecure. I mean, I didn’t know—I still don’t know. I haven’t seen all of it.

Right. In film world, you have to trust directors and editors to do all sorts of thing to your performance after you’ve given it. But then maybe that’s not unlike your experience as a stage director, leaving it in the hands of the actors after rehearsals are over.
Correct. It was a wonderful extra perk to be able to tune into Michael across the room from me, doing his version of what I do and with a different instrument. I could tell when he would be stressed but not showing it. I could tell when he needed to be encouraging for somebody who was insecure.

From Comeback fan to Comeback fan, tell us what you thought of this new season.
They delivered a miracle. It’s really about something. Lisa keeps saying it’s the perfect trilogy, that it puts the cap on everything they were playing with. The character, her journey, what she puts herself up against… some of it is so fucking funny you can’t believe, and she’s such a genius so you’re totally invested, too. I wouldn’t have thought it possible, but If I’m going to have one shot at this acting thing, this was definitely the one to do.

One shot? Does that mean this isn’t something you plan to pursue, that we won’t see you onstage on Broadway?
I don’t think so! I’m at the point in my life where I’m so grateful to still be working. I have three plays ahead of me and two musicals. Not announced, not guaranteed, but I’m working on five different properties right now, and I’m on my way to 87. I have to say thank God and thank everybody around me, because I’ve never had a better time. I guess if the question was posed to me, I’d be inclined to say yes!

I would be remiss if I didn’t ask if you think we’ll get Lisa on Broadway any time soon.
You know, she’s not a theatre animal. We had a long talk about it. She started with The Groundlings and what not, and I think she maybe did one play in her life. But she has no interest in it at all. And she’s not Valerie. She’s a very different woman—wonderful, dimensional, smart. She’s very much her own character. But she has room in her imagination and art to create something so remarkably real that the character touches us. It’s a character that carries with it a lot of our own insecurities and our own needs. You can’t ask for more than that.