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To Play Transgender, Sandra Caldwell Had to Open Up About Who She Is

The show’s casting director, Adam Caldwell, could tell she was nervous. (They are not related.) But he was struck by her energy and charisma, and how exactly she matched the description of the character. He and MCC had been struggling to cast the part for months.

He sent a message to William Cantler, an artistic director of the theater: “I think you should come to Studio 6.” Mr. Cantler did. After a work session with the director Will Davis and a callback — in which, Mr. Cantler said, Ms. Caldwell “took control of that room” — they offered her the part. She burst into tears. So did Mr. Dawkins.

Now in rehearsal, Ms. Caldwell has largely worked through those initial nerves. Her stage presence is powerful: On a recent afternoon, after a successful run-through of a tense early scene, she did a full-body dance around the perimeter of the room, then pumped a fist.


Left, Will Davis, the director of “Charm” and right, Philip Dawkins, its playwright. Center, Gloria Allen, the inspiration for the play’s lead character.

Da Ping Luo

“She’s working so hard,” Mr. Davis said. “She really wants to get this right.”

“Charm” follows a crew of teens and 20-somethings from wildly different backgrounds who attend etiquette classes at an L.G.B.T.Q. youth center in Chicago, taught by Mama Darleena. Many of the characters are transgender, and Mr. Davis, who is trans-identifying, felt strongly that the parts went to people whose gender identities matched the roles.

In a theater world where jobs still remain heavily white and male, it is not surprising that parts for trans-identifying actors are limited. In his experience, Mr. Davis said, theaters often give familiar reasons for not casting actors from historically marginalized groups: “The same two things get said. ‘One, I can’t find them, two, they’re not trained.’ So I feel very, very strongly that it’s actually the responsibility of the institution to find and train them.”

MCC used nontraditional methods to find actors for the nine-member cast. They put out a call on social media, tried networking through friends, and reached out to lesbian and gay youth centers and organizations. They tried to cast a net well beyond New York City and Los Angeles.

Mama Darleena was a particular challenge. “The fact that a trans woman of color in her 60s is alive is a miracle in and of itself because of the oppressive ways that that group of people has been treated in the last 60 years,” Mr. Davis said. “The idea that then on top of that, that person was an actor was a really tall order.”

In the 2015 world premiere production of “Charm” in Chicago, Mama Darleena was played by a cisgender man, meaning he identifies with the sex he was assigned at birth — though in three other productions, she has been played by transgender women.

Ms. Caldwell was born in Washington, D.C., but she ran away to New York several times, beginning when she was 13 — her way, she said, of “figuring things out.” When she was 18, she bought a $6 ticket to a Broadway show. “I didn’t know what it was, I just saw the lights,” Ms. Caldwell said. It turned out to be the Stephen Sondheim musical “Follies,” starring the original cast. “I knew right then that this was what I wanted to do,” she said.

She completed her transition around the age of 19. Her mother, with the help of two friends who were involved with L.G.B.T.Q. issues, brought her to counseling and psychiatrists, before she received hormone therapy. Afterward, Ms. Caldwell said, “I felt a lot of joy, and also relief.”

“Back then,” she added “the rules were, you did what you had to do and kept your mouth shut.” Outside of her family, only a small group of friends from Washington who had known her as a child were aware of her transition.

She auditioned for a role as showgirl in New York — and ultimately traveled to Europe and worked at the Moulin Rouge. She had success as an actress. She wrote a one-woman show seven years ago about her life and travels, “The Guide to Being Fabulous After You’ve Skinned Your Knee.” She performed it at Berkeley Street Theater in Toronto, where she lived for more than a decade.


At 65, Sandra Caldwell has begun to reveal that she is transgender. She’s playing a character who’s very similar to her in “Charm.”

Tony Cenicola/The New York Times

But she never mentioned her transition. After that show, “the bottom fell out because I felt like I was lying,” she said. “I had left myself out. I left the truth about me out.”

Eventually, Ms. Caldwell said, she came to a conclusion: She wanted to start sharing that truth with the world.

About a year ago, she approached Alicia Jeffery, her manager of 14 years. Ms. Caldwell confessed to her that she’d transitioned many years ago, and was ready to share it with the world.

“I had absolutely no idea,” Ms. Jeffery said. “She was known around Toronto to be this very foxy, sexy actress and singer. Which is what she is.” They discussed how she might rework her one-woman play to include her transition, and how she might begin to share her story publicly.

Shortly after, Ms. Jeffery saw a casting call for “Charm,” and the description of Mama Darleena. She asked Ms. Caldwell if she wanted to be submitted for the part, and Ms. Caldwell said yes. “Well, here we go,” Ms. Caldwell recalled saying.

Ms. Caldwell said she was drawn to the play in part because it wasn’t a tragedy. “Some movies with a trans theme — not so much anymore — but they always used to start with somebody being beat up,” she said. “Or somebody being hurt. This has nothing to do with that whatsoever. All it touches is this woman who has a gift, a skill to help these folks along.”

Ms. Allen, on whom her character is based, is 72 and still lives in Chicago. She no longer teaches etiquette classes, but she recently flew to New York to meet the cast of “Charm.”

Of Ms. Caldwell, she said, “I met her and I fell in love with her right then and there because she is so down-to earth, and so classy, and I said ‘O.K., I see myself in her.’” They’ve become friends.

Ms. Caldwell knows that once the play opens on Sept. 18, much more may change for her. This is the first time she is sharing her gender identity in an interview.

“I don’t know what it’s going to be like,” she said. “But I kind of want to live the rest of what I’ve got on this planet as if there’s such thing as complete freedom. I want to live in that.”

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