Tony-award winning director Jack O'Brien talks about career, life in CT

It’s a misty autumn afternoon and along a winding country road in New Milford, a housing development emerges of stately though modestly-scaled homes with manageable lawns and pristine porches.

In one of the dozen or so homes in this quiet mini-village is where theater director Jack O’Brien has lived for the past 10 years.

“I call the style of home ‘Early Ozzie and Harriet,’ ” he said laughing, as he greets his visitors.

Like the avuncular man himself, the two-story house reflects a sense of the classic, the playful and the practical.

Over a six-decade career in the theater and nearly 50 Broadway credits, O’Brien has earned three Tony Awards and in June received another for lifetime achievement.

At 85, he’s still achieving plenty.

This fall on Broadway he directed close chums Patti LuPone and Mia Farrow — who live nearby — in the Jen Silverman comedy “The Roommate.” He also launched the national tour of the 2023 Broadway musical “Shucked,” which earned him his seventh nomination. He is readying to cast the musical for its London premiere and for 2025 he will be working on a Broadway-bound revival of “The Sound of Music.”

“Let’s go upstairs,” O’Brien eagerly said, leading his guests to a large alcove whose walls are covered with production photos, design sketches and posters of some of the hits (and misses) of his career. To comfortably take it all in there’s a butterscotch-colored leather couch, accented with a colorful variety of textured pillows.

“Isn’t this fun?,” he said taking a seat, clearly pleased in showing off the room to a theater aficionado. “And this isn’t even everything!”

It’s a theater archivist’s dreamscape: memorabilia that goes back to the start of his career with the APA Phoenix Repertory Company in the ‘60s; the launch of his Broadway career — in the ‘70s with an acclaimed production of “Porgy and Bess;” his years as artistic director of San Diego’s Old Globe and its Broadway transfers in the ‘80s and ‘90s; a string of hit musicals and collaborations with Tom Stoppard in the 2000s; more awards and nominations in the 2010s; and his latest nomination in the 2023 for “Shucked.”

For each piece of the past, there’s inevitably a backstage tale and O’Brien is known to be one of the best theater storytellers in the business, the person you most want to sit next to at dinner. He has authored two anecdote-filled memoirs, the last being “Jack in the Box or, How to Goddamn Direct.”

The airy second floor is for overnight guests and those who might enjoy looking at his theater collection, he said. For himself, well, O’Brien is just too busy to overindulge in nostalgia, residing on the ground floor.

“I have no rear-view mirror,” said the upbeat director. “I only look forward.”

Connecticut — and specifically Litchfield Country — has been O’Brien’s refuge from the demands and chaos of Manhattan for nearly 25 years, initially wooed by theater pals who lived here.

“Lindsay Law, who produced all my television shows (for PBS’ “American Playhouse” in the ‘70s) lived in Roxbury and I would come up to visit every weekend,” he said.

Following the death of his partner, composer James J. Legg Jr., in 2000, O’Brien decided to create new memories in the serene corner of Connecticut. He bought a sprawling homestead which he named “Imaginary Farms,” after the 2002 Broadway play he was directing at the time, “Imaginary Friends.”

”It was the house that ‘Hairspray’ built,” he said, referring to his 2002 hit musical.

“It was gorgeous,” he said of that first home, noting its swimming pool, guest house and 20 acres. “We always had loads of friends there. I traditionally cooked Thanksgiving or Christmas for (composer Stephen) Sondheim and all our friends.”

“But several years ago my financial advisor said to me, ‘You can’t keep this house because it takes three staffs of people to run it.’ So I said OK, and I made a video of the place and sent it to all my theater people, most of whom had been guests there at one time or another.’

Ethan Hawke, whom O’Brien directed in Stoppard’s “The Coast of Utopia” trilogy and Shakespeare’s “Henry IV” and “Macbeth,” bought the house “And everything in. He said, ‘We want to live like you live.’ I feel so wonderful about how it all turned out.”

After selling his apartment on Central Park West 10 years ago, he sought a return to Connecticut. He learned that a new development was being built in New Milford, and that he could customize a home to his tastes, which one might call a slightly different kind of directing.

“The entire development looks like the back lot of MGM in 1945,” he said. “And by that I mean quite charming. It’s perfect for me now.”

O’Brien leads his guests to his ground-floor bedroom where on display are shelves of his multiple awards — including his Tonys, an armful of Drama Desk trophies, and the Theatre Hall of Fame honor. On the floor there’s a throw rug created by stage designer David Rockwell completely made up of colorful satin bow ties.

In the living room, he eases into an oversized, wing-chair next to a marble fireplace, as Coda, as if on cue, jumps into his lap.

“I’ve had four Yorkies in my lifetime and Coda (is) the last of a distinguished line,” he said, seemingly a nod to his own age more than his dog’s.

It is pointed out to him that legendary theater director George Abbott lived to be 107 and continued working until his death in 1995.

“I met him when he was 105,” he said, referring to the time O’Brien directed a revival of “Damn Yankees” starring Jerry Lewis. Abbott was protective of his original script which O’Brien sought to rewrite. “Those extra two angry years kept him alive,” he said.

“I guess there’s something about theater directors. Twenty years ago, I didn’t know anyone in their 90s. Now I know a lot and many of them are still working. I’m working all the time now, too. It’s ridiculous. I thought it was going to stop — but it didn’t.”