La Jolla Playhouse’s outgoing artistic director Christopher Ashley reflects on his 18-year legacy

Next month, San Diego theater audiences will say goodbye to Christopher Ashley, the company’s  Tony Award-winning artistic director who has led the company since 2007.

During his nearly two decades at the artistic helm of the Playhouse, Ashley has sent 20 shows to Broadway, created the company’s popular annual WOW Festival, established the DNA New Work Series, which has produced more than a dozen world premiere plays, and has directed nearly two dozen plays and musicals.

Christopher Ashley names his 13 favorite La Jolla Playhouse productions

He also established an annual residency program for itinerant local theater companies, provided a new home for the Latinx Play Festival, which was left homeless by the shutdown of San Diego Repertory Theatre in 2022, and has helped launch several new programs including the annual Director Fellowship, paid internships and the Veterans Playwriting Workshop.

And perhaps most thrilling for local audience members, Ashley’s deep roots in New York’s theater community have helped him lure some of the industry’s top artists to La Jolla to develop new work, including playwrights like Moisés Kaufman, John Leguizamo and Anna Deavere Smith, musical theater composers like Joe Iconis and David Bryan and Broadway stars like Idina Menzel and Matthew Broderick.

In January, Ashley will begin the process of moving back to New York City, where he has an apartment near Washington Square on a street recently renamed in honor of playwright Terrence McNally. Ashley will serve as the new artistic director of Manhattan’s Roundabout Theatre Company, one of the largest and most prestigious nonprofit theaters in America. He will oversee programming for its three Broadway and two off-Broadway theaters.

La Jolla Playhouse’s Christopher Ashley tapped to lead New York’s Roundabout Theatre Company

Ashley was hired for the Roundabout job in September 2024, so it has been a long goodbye. But he said it’s still a bit sad because he’ll miss his friends and colleagues here, as well as the region’s sunny, laid-back lifestyle. “I love the indoor-outdoorness of San Diego. That’s so delightful. And during the craziness of the pandemic, there was no place I’d rather have been.”

Earlier this week, Ashley spoke with the Union-Tribune in a wide-ranging conversation about his proudest achievements, how the Playhouse audience has changed over the years and his favorite shows. These answers have been slightly edited for length and clarity.

Q: As you wind down your time at La Jolla Playhouse, do you feel like you accomplished everything you hoped for?

A: I don’t think you can ever could accomplish everything, but I definitely also appreciate change in theater organizations and in the arts. There’s something about making room for new ideas, new blood, new people. It feels like 18 years is a good sweet spot. We did a big long runway of almost a year and a half from when I said I was leaving, so that’s given time for a lot of really beautiful conversations about what La Jolla (Playhouse) has been, what it is now and what it could be in the future. So it’s certainly bittersweet, but mostly sweet.

Q: Are there any lessons that you learned in La Jolla that you’ll take to Roundabout?

A: My experience of running the Playhouse has been the relationships that I have built here.

I’ve been working with an incredible staff that’s top notch. I do think the staff is full of people who understand our mission and are passionate about the work they do and they are true artists.

I could not imagine the last decade without my partnership with the incredible (Managing Director) Debby Buchholz, who I cannot say enough amazing things about.

Our board is second to none. They really understand our mission here. I’ve enjoyed the experience of working with them for 18 years as they charted the long-term course of the Playhouse, figured out how do we solve the problems we have, how do we make new opportunities and how do we create the most humane organization that we can.

Then the third group I want to talk about is San Diegans, both other theater-makers and also our audience.

I think it’s such an exciting theater community and it’s been a real privilege to be a part of it. I’m going to miss going to all the amazing shows that the San Diego theatermakers make.

I’m also going to miss the buoyancy and ambitions of our audience. One of the things I’ve always loved about our audience is that they’re adventurous in the best way.

I feel like so many of the people who come back to the Playhouse year after year want to see something new, want to stretch themselves and want to be part of making a mark on the American theater.

Q: One thing I’ve noticed in covering the Playhouse over the past 30 years is how it has cultivated an audience hungry for ambitious new work. How did that happen?

A: This audience has dug deeper and deeper into the sense of empowerment and ownership in the creation of the work in a way that I love.

You talk to the people in the aisles and lobbies and it’s amazing to see how complete their understanding is of the life that these shows have after they leave the Playhouse. Many of our audience members can tell you where it went on to, how long it ran, whether it was made into a television show and whether it’s been published. This audience feels like they’re midwifing new life into the world.

I think I’d argue that that audience does have something to do with that show finding its best self. A lot of artists will say to me ‘Can you consider programming our play? Please do it in the winter so I can come to La Jolla in the winter,’ but also they say ‘I want to watch my show take its first steps with your audience.’”

Q: During your tenure here, you’ve sent far more new shows to Broadway than your predecessors. What do you credit that to?

A:  It’s all relationships. I have been in the world of making new plays and musicals for enough years that I know a lot of the players, so when I got here they immediately started to call, as I know they did for (previous Playhouse artistic directors) Des McAnuff and Michael Greif.

And the first show I directed here was “Memphis,” which went on to Seattle and on to Broadway (where it won the 2010 Tony Award for Best Musical). That helped pave the way.

Our space (the Mandell Weiss Theatre) is exactly what you’d want to try out a show that has Broadway aspirations. It’s got the width, the height, the traps, the flys and the backstage space, and its only 500 seats so it’s kind of the perfect space. And if you want to do something that’s outside the box, the Potiker is also a beautiful space, that’s where we started “Come From Away” and “Redwood.”

But I also always think about how do we center the work that isn’t Broadway-bound and never will be or should be. This is a theater that has had real success in moving things to Broadway and also incredible investment in shows made in San Diego for San Diegans.

Q: Over the years you’ve brought a lot of high-profile artists to the Playhouse. Who are some of your favorites?

A: Moisés Kaufman’s play “33 Variations” was in the first season I programmed 18 years ago. I have loved having Moises as a peer and collaborator and he’s an incredible artist who has made a home here.

La Jolla Playhouse aspires to be one of the great theaters, and you are only as great as the artists who make a home here. So the opportunity to make a home for artists is the center delight of this job.

I think of (San Diego resident) Delicia Turner Sonnenberg who is about to direct her fourth play for us and she also sits on our board. I think of Des McAnuff, who has very much remained in our lives.

I think of Anna Deavere Smith, who I worked with before I got here on “Fires in the Mirror.” We did a wonderful production of “Let Me Down Easy” with San Diego Rep in their space and she did “Love All” here (in 2023). She’s one of the great artists of the world.

I also think of Charlayne Woodard has also been on our board and we’ve produced several of her plays.

Q: The WOW Festival must be your most popular signature program. How did you come up with the idea?

A: When I arrived I was talking a lot about the idea of a festival and San Diego is such a natural place for one.

The regular theatergoing model is where you buy your ticket a couple months ahead, sit in the same chair facing the stage and maybe you’ll talk about the show on the car ride home. What I love about festivals is that you show up, there’s going to be food, there’s going to be drink and there’s going to be impulse. You might have tickets for something but then you hear about something else while you’re waiting in line and run over and see a show that you had no idea until that momen that you were ever going to experience.

With the WOW Festival, I do love how that kind of a form challenges artists to think differently about their story. And boy was it useful to us in the pandemic. We went to all the artists we’d produced WOW shows with and said do you want to make something digital and virtual? We created 14 pieces during the pandemic. It was a very satisfying time to be able to write a paycheck to artists.

Q: Your DNA New Work Series  has been very successful at turning play readings into world premiere productions. In its 12 years, more than a dozen scripts have gone on to season productions.

A: I give huge props for that to Gabe Greene (the Playhouse’s director of artistic development), who runs it. He arrived the same month I did 18 years ago and he’s very much been the producer and motor of that reading series. It’s been amazing.

We very much try to think about programming plays that had not been read extensively. We were more interested in giving authors a first look at their show, the first time it’s ever been read or first time with professional actors. That’s been a real service to the authors but also tremendously useful for us in finding new material for subscriptions.

Q: You launched the Resident Theatre Program in 2010, which has provided free performance space and technical support for San Diego theater companies without a permanent performance space. Some of those resident companies have since closed down, but some have grown and established permanent homes. Where did the idea for the program come from?

A: I looked at our calendar when I arrived and saw that we have four spaces which we share with the university, but there were big chunks of time when we weren’t using them. That seemed sacrilegious to let the theaters go empty.

Alsom during  my first couple of months here (in 2007), I tried to get to every small, medium and large-size theater in town to see what everybody was up to. There was so much strong work and so many programs in San Diego between UCSD, SDSU, USD and City College. All these great programs are training new generations of artists who were going to make their home in San Diego. So it seemed to be such a natural fit.

It turns out that a rent-free space with some lighting and sound help is actually incredibly helpful to certain organizations right when they’re at the pivot of making a step toward more institutional maturity. The ones that continue on I’m so proud of them, and the ones that burned bright but are no longer with us, I champion the memory of their work.

And all of those artists and their work has been a kind of lifeblood for the Playhouse.

Q: Besides serving as artistic director, you have also directed 21 plays and musicals at the Playhouse, as well as some WOW and DNA shows. Why has it been important for you to do both?

A: For the way that I did the job, it’s indispensable.

As an artist who makes their work here and also as an administrator who runs it, that time spent in the rehearsal room turns out to be a key part of reinvigorating the mission and understanding why we do what we do.

Q: Do you have any advice for the Playhouse’s incoming artistic director Jessica Stone?

A: I resist giving advice. The way that she finds would be better than anything I’d chart out for her.

But I definitely suggest getting out to see as many things in San Diego as you possibly can and dive deep into the theater community here. Make yourself as accessible to the audience as you can. That’s been a great part of the job.

And I do think this is an organization that can dream big, so don’t edit yourself ahead of time. Just think about the most exciting theater you can make it, and I know she will.

Veteran stage director Jessica Stone named La Jolla Playhouse’s next artistic director