Sandra Caldwell thought she'd lose her career for being trans. Instead, she was celebrated

Sandra Caldwell is a prolific actor and playwright with dozens of films and TV shows to her name, including The Book of Negroes, The Cheetah Girls and Shall We Dance.

Now, Caldwell is the writer and star of her own stage show, The Guide to Being Fabulous, which details her extraordinary life — a life started by her decision to run away from home.

"I wasn't running away from anything because there were no problems at home, everybody understood," she tells Q's Tom Power. "I don't know how they understood, [but] they understood that I was a gay child."

From her home in Washington, D.C., Caldwell made her way to New York City with dreams of Broadway and the legendary Ballroom Scene.

It's been a momentous journey for the actor, but there was something she'd been hiding her whole life.

"I didn't know what being trans was at 13…. Where would I get the reference from?" says Caldwell. 

Telling the world

After decades in the industry, it was only in 2017, in her 60s, that Caldwell came out publicly as a trans woman.

While performing as a 67-year-old, Black, transgender woman named Mama Darleena Andrews in the play Charm, Caldwell revealed her identity via the New York Times. 

"I thought, 'my career is over,'" she recalls. "I was more worried about my husband than I was worried about myself because I knew it was going to be in the New York Times, and that's not a small newspaper."

But much to Caldwell's surprise, the opposite happened, and soon she was being invited to meetings with major companies in film and TV production. After years of trying to claw her way to the limelight, her celebration as a trans woman initially annoyed her. 

"I was pissed off for a long time after Charm," she says. "Now you get all these freedoms. Now it's a good thing to be trans. It's free to live openly. I used to feel hurt that I didn't get to have that privilege."

In seeing the reaction to her show, Caldwell has now become much more comfortable with being an elder icon for a younger generation of trans people.

Her family was always understanding of her identity, especially her mother — who supported her through her transition. 

"She raised the money for me, she went through every psychiatry meeting, she went through it all," says Caldwell. "She never flinched. She never asked me if, 'This is really what you want to be?' She never questioned me."

Making it in New York

Having run away to New York at just 13, Caldwell found herself working the streets amongst people with similar stories. She would be involved in panhandling, as well as sex work, while there. 

"I moved to New York, and New York was a bit dangerous at that time," she says. "I sometimes want to recall how I lived or how I survived it, but it just happened. Life just started to happen [and] years just seemed to pass away, and I met the group that I would eventually hang out with."

Eventually, Caldwell found herself at the centre of the Ballroom Scene, where she would be inspired. 

"It was fantastic, it was glorious," she tells Power. "It was like you go into these three or four in the morning balls and you could see people that were changing their clothes on the streets and getting ready with the finery."

"It was very glamorous, but like everything that day it had a little hustle to it."

The full interview with Sandra Caldwell is available on our podcast, Q with Tom Power. Listen and subscribe wherever you get your podcasts.

Interview with Sandra Caldwell produced by Lise Hosein.

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