On an afternoon last month at La Jolla Playhouse, the director Christopher Ashley was everywhere — at the lip of the stage, on the stage, then at a desk balanced across a row of seats in the darkened auditorium, then crowded around a piano in a rehearsal room, helping an actress learn a new version of a song. He whispered with actors, conferred with choreographers, huddled with designers. Blocking out a wedding scene, he adjusted a dancer’s stance inch by careful inch.
Ashley was preparing for a preview performance of a new musical adaptation of “Working Girl,” the beloved 1988 Cinderella story of ambition and moxie. The film had been reworked by the writer Theresa Rebeck and set to new music by Cyndi Lauper. Before the curtain rose that night, Ashley had to implement a new Act I finale, reworking about 15 minutes of stage time in a single day. Through it all, he was remarkably serene, at least on the outside.
“I learned over the years how to seem calm,” he said, smiling benignly.
Rebeck, who was also at the rehearsal, compared him, favorably, to an octopus. “There’s a central intelligence and then there’s all sorts of arms with other kinds of intelligence that reach out to all the different kinds of people involved in an enterprise like this,” she said.
In “Working Girl,” a fake-it-till-you-make-it-parable about a financial services secretary with corner office dreams, the heroine has to pretend expertise she doesn’t yet possess. Ashley doesn’t have that problem.
A Broadway director since the late 1990s, Ashley, 61, has spent the last 18 years at the Playhouse, situated in a bucolic spot in San Diego. During that time, 20 shows that the Playhouse has helped to develop have made their way to Broadway, winning 16 Tony Awards. Ashley directed four of those, and took home his own Tony for his direction of “Come From Away.”
“He has the magic touch,” said Amanda Zieve, a lighting designer who has worked with Ashley often. That magic sometimes eludes him, though: Ashley directed the recent Broadway flop “Diana.” And then there’s “Escape to Margaritaville.” Still he claims to love them all. “You learn the most from the things that don’t gel,” Ashley said. “Those are the ones you keep thinking about, like, ‘OK, what could I have done differently?’”
On Broadway, Ashley occupies a nifty position. A specialist in musical comedy, his taste skews populist. (“He is kind of a man of the people,” Rebeck said.) For worse and mostly for better, he is committed to imparting delight.
“I don’t forget joy,” he said.
A few years ago, Ashley began thinking about one further career milestone. He also missed the change of the seasons, and the zing and pizazz of the New York theater ecosystem. He wanted a place that could combine two impulses, “to make a home and to make a town square.”
That place was the Roundabout, which had been searching for a new leader since the 2023 death of Todd Haimes, its longtime artistic director and chief executive. One of New York’s largest nonprofit theaters, the Roundabout oversees three Broadway houses, one Off Broadway space and a black box. Katheryn Patterson Kempner, the chairwoman of Roundabout’s board, said Ashley’s La Jolla tenure and his respect for what Haimes had built had impressed the search committee.
“He understands the multiple missions of, and challenges for, a not-for-profit theater,” she wrote in an email. Ashley’s appointment was announced in September 2024, with a start date of July 2026. “Working Girl” will be his final show at La Jolla as a director.
“It feels like a great last project because of how much fun I hope it’s going to be,” Ashley said.
Before he was a director, Ashley was a child actor. His parents married early and divorced early, and his childhood was largely itinerant. But he did theater — school plays, summer stock — anywhere he could. Onstage, however, his mind was busy, wondering about a better place to stand, a different way to deliver a line. “I was always directing myself, which is not really a great way to act,” he said. He took up directing in high school and continued it at Yale, where he studied English.
After a few years as a systems analyst, a job meant to chip away at his student debt, he returned to theater, taking internships and fellowships. His early successes include two solo plays, Anna Deavere Smith’s “Fires in the Mirror” and Claudia Shear’s “Blown Sideways Through Life,” as well as Paul Rudnick’s 1992 play “Jeffrey,” a comedy about AIDS that he directed just as he was coming out as gay. “It was answering the need to laugh in those situations,” he said of “Jeffrey.”
By the early 2000s, he had taken several shows to Broadway. Moving to a sleepy, moneyed enclave like La Jolla wasn’t the most logical next step. But two of the institution’s previous artistic directors, Des McAnuff and Michael Greif, had built the Playhouse into a year-round artistic hub and a space devoted to the development of new work. And after more than a decade spent as a freelance director, a professional state of being that he compared to dating, he felt ready to commit to an audience.
“I was really hungry for the kind of relationship with them that you can have across six plays a year,” he said.
After 18 years, he has presented more than 100 plays, as well as Without Walls, a free festival of immersive work that Ashley inaugurated; a new works series; and a resident theater program open to local companies. Ashley also moved the Playhouse to a paid internship system, established a fellowship for directors of color and oversaw other initiatives, including a performance outreach program that tours local schools.
“We were in quite good shape, we were on the map, and still he came in and transformed the Playhouse,” Debby Buchholz, the Playhouse’s managing director, said.
Buchholz said she was sad about Ashley’s departure, though excited to see what he would next achieve. “I cannot think of a single person who is happy to see him go,” she said. “But there’s a recognition that he has been with us for a wonderfully long period of time, that he has grown the theater in a beautiful, intentional way.” (The Playhouse has named Jessica Stone, who directed “Kimberly Akimbo” and “Water for Elephants,” as its next artistic director.)
Before Ashley’s departure, he allocated two directing slots for himself: “Working Girl” and “The Heart,” a new musical, based on a French novel about a heart transplant, which premiered in August. A story about generosity and what even strangers might give and what they might owe, “The Heart” had a humanity that felt, Ashley believed, like useful counterprogramming to the current political moment.
I attended a run-through of “The Heart” shortly before previews began and watched Ashley move among the cast and the creative staff, giving his notes gently and privately. “He does not insert himself with a heavy hand, ever,” Ian Eisendrath, the co-composer of that musical, said in a recent phone interview. “He’s very considerate and aware of others.”
Ashley showed that same consideration to “Working Girl,” a heftier affair, with a 19-person cast, based on a beloved pop culture artifact. If Ashley were readying the show for Broadway, he would want it to be perfect. At La Jolla, he could hold himself a little more loosely, knowing that the Playhouse was one step in the musical’s development.
He agreed, mordantly, with the adage that musicals are never really finished, just abandoned, but during a long rehearsal he kept any frustration in check, stopping to chat and to recommend a favorite fish taco stand. “This chaos, this whole environment, creating a new musical, and all these moving parts that may or may not need adjustment, that is the world where he lives,” said Zieve, who had spent the long rehearsal day with him.
A few hours later, Ashley stood before an eager audience and thanked them for coming, saying, “Your presence here is crucial as we develop this new American musical.” Then he slipped back into the dark, ceding the stage to the story.
The audience seemed enthusiastic — laughing, cheering, rising to their collective feet at the close of the title number, which is also the current finale. (Lauper had written one further number, “Picture It,” but Ashley hadn’t had time to stage it.) At its fifth preview, “Working Girl” wasn’t the weightiest show or the most relevant. For those assembled, it could still dispense delight.
“I’m glad the joy is visible,” he said on a phone call the following morning. “Because it’s definitely one of the things theater does best.” Certainly, it’s what Ashley does best. And as he prepared for his own professional final act, it was enough.
Alexis Soloski has written for The Times since 2006. As a culture reporter, she covers television, theater, movies, podcasts and new media.
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