It was the role of a lifetime: the central character in a timely play at a well-respected Manhattan theatre. For Sandra Caldwell, who left a successful acting career in Toronto 13 years ago and moved to New York, it had next-level-break written all over it.
But to embrace the role of the transgender Mama Darleena Andrews in Philip Dawkins’s play Charm at MCC Theater, Caldwell felt compelled to publicly declare a truth she’s kept hidden for over 40 years: that she is trans herself, having gone through gender transition in her native U.S. in her early 20s.
Many Toronto arts lovers will likely find this surprising. Some might remember Caldwell, who is now 65, from her 1997 Dora-nominated performance in Sophisticated Ladies; or from her featured role in the musical Anything That Moves at Tarragon in 2001. Among her nearly 50 TV and film appearances is the role of Georgia in The Book of Negroes. Music lovers may recall her Sunday afternoon Jazz FM show.
During her over two-decade Toronto career, Caldwell was accepted as a woman — by her own description a “little whippersnapper fireball,” a Tina Turner type. If anyone suspected that she was trans, they didn’t let on.
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In the early 2000s, though her career in Toronto was still going well, Caldwell became overwhelmed by the new societal openness around gender and sexuality. “I heard the words LGBTQ, all these new words, and I felt like a crazy person. . . . The more I saw the more confused I got, about how much I could do or how much I could realize.”
Writing and performing a one-woman show around that time added to her distress, because she didn’t include her gender transition in the story: “I erased the first half of my life. It sent me into a depression.” The person she felt she was most letting down was her mother, now 85, who supported her at every stage of her transition.
“I disrespected my mom because she’d held my hand for so long . . . that’s when I walked away.”
She moved to New York: the city where, as a teenager, she’d first discovered the transformative potential of theatre at a production of Stephen Sondheim’s Follies. While her personal life got on track — she’s been with her current partner for nine years and they live in Rhinebeck, N.Y., about an hour north of the city — she was still “waffling in and out of her career,” feeling more and more she was living a lie by not identifying publicly as transgender.
About a year ago, as the profiles of trans people in public life and the entertainment industries reached a certain peak, Caldwell finally felt ready. She flew back to Toronto and, with her close friend and former agent Carol Amirault by her side (the only person in the business who knew her secret), came out as trans to her current agent, Alicia Jeffery.
“Alicia said, ‘Well, how do we proceed?’” remembers Caldwell, relieved that Jeffery didn’t show her the door. Two weeks later, Jeffery started including the fact that Caldwell is trans in her approach to casting agents and “we couldn’t believe what started to happen,” says the actor. “We had calls from four separate companies who wanted to see me; it was amazing.”
Then came the call to read for the part of Mama Darleena — a trans woman who starts an etiquette class for LGBTQ youth in Chicago, based on the real-life figure Gloria Allen — and it was like “the universe opened up and handed me a gift,” says Caldwell.
She got the part and was two weeks into rehearsals when another opportunity presented itself: a high-profile story in the New York Times arts section, revealing her connection to the role. Her nerves flared up again — “which is not a good thing, when the play is 94 pages long and I am on 86 of them!” — but response to the story was generous and gratifying.
“The first text I read was from my partner’s brother,” who had not known her background. “He said, ‘I want you to just remember that the world is always filled with haters, but you have done a most courageous thing and you are loved. Our family loves you.’”
The critics loved her too. Variety’s Marilyn Stasio called Caldwell a “black transgender woman of immense poise, beauty and — pardon me, I can’t help myself — charm,” and New York magazine’s Sara Holdren praised her as “classy and charismatic.”
More opportunities have arrived, including meetings with American network television and, to Caldwell’s delight, not just for transgender roles. “They are seeing me for anything and everything . . . nobody’s saying, ‘Send me that trans woman’; they’re saying, “Send me Sandra Caldwell I saw in that play.’”
Caldwell has written a new version of her one-woman show, this one telling the full story, and she’s shopping it around to theatres in New York and Toronto.
To come back here and perform her whole truth? “What a dream that would be.”
Karen Fricker is a Toronto Star theatre critic. She alternates the Wednesday Matinée column with critic Carly Maga.