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Sandra Caldwell, centre, on stage with Tiffany Deriveau, left, and Miss Niki Nikita, right, in her autobiographical show, The Guide to Being Fabulous.DAHLIA KATZ/Soulpepper

  • Title: The Guide to Being Fabulous
  • Book and lyrics by: Sandra Caldwell
  • Music by: Sandra Caldwell and James Dower
  • Additional music and lyrics by: John Alcorn
  • Additional dialogue by: Marilyn Jaye Lewis
  • Director: Weyni Mengesha
  • Actors: Sandra Caldwell, Tiffany Deriveau, Miss Niki Nikita
  • Company: Soulpepper
  • Venue: Young Centre for the Performing Arts
  • City: Toronto
  • Year: Runs to Nov. 12

Critic’s pick

“Child, this is a lot of words!” exclaimed Sandra Caldwell, while taking a pause during the opening night of her autobiographical show The Guide to Being Fabulous.

After the eclectic life Caldwell has led, she’s entitled to drop the occasional line, glance at an onstage video prompter and take a breather from her 90-minute show to just soak it all in. She’s earned it. Who cares about being word perfect when what you’re after – to borrow a term from the New York drag balls she took part in at one period in her life – is realness?

Search Caldwell’s name on and you’ll see dozens of credits, including The Book of Negroes miniseries, the TV show Soul Food and the Jennifer Lopez/Richard Gere movie Shall We Dance. Her Canadian stage appearances include her Dora Award-nominated performance in the Duke Ellington revue Sophisticated Ladies in the late 1990s as well as an earlier version of this show called The Guide to Being Fabulous After You’ve Skinned Your Knee.

But what none of her professional bios reveals is the hardscrabble early life she lived, or the fact that she had been assigned male at birth, transitioned in her early 20s and essentially hid this fact for decades until 2017, when she came out as a trans woman in Philip Dawkins’s off-Broadway show Charm.

In this version of her show, the second premiere in Soulpepper’s Her Words Festival, Caldwell bravely fills in some of the gaps in her story. And while she leaves some important questions unanswered, her storytelling savvy, innate musicality and undeniable stage presence still shine through.

Open this photo in gallery:

In the telling of her eclectic life, Caldwell leaves some important questions unanswered, but her undeniable stage presence still shines through.DAHLIA KATZ/Soulpepper

Wearing the classic Broadway veteran outfit of untucked white blouse and black cigarette pants (Ming Wong designed the costumes), Caldwell recounts her early life in the U.S. By 13, she had attended as many schools as she was years old. When her single mother moved the family to a Virginia farm ruled by an abuser, she ran away and soon discovered the seductions and gritty charms of Washington’s Dupont Circle.

Caldwell’s writing in this section is among the most vivid, as she describes the infamous neighbourhood as an alternate Oz, where the philosophy was to get money by any means necessary.

“My munchkins,” she tells us, “were pimps, prostitutes and runaways like me.”

Soon she’s learning how to panhandle and pick pockets. The latter activity leads to her first arrest. And when, at 16, she finds herself in a life-threatening situation with her first john, a neighbourhood sex worker named Joann (Tiffany Deriveau) rescues her and sets her up with work at a local cafe. Once there, she’s introduced to burlesque dancers who drop by after their shows, which leads to her own apprenticeship in live entertainment.Learning burlesque leads to discovering the then burgeoning drag ballroom scene in New York, which leads to work at the legendary Club 82 and a meeting with iconic European superstar Romy Haag (Miss Niki Nikita). When the latter extends an invitation to join her in Europe, Caldwell realizes she has no official documents. This in turn leads to one of the show’s quietest and most moving sequences in which she briefly reunites with her mother (Deriveau again).

There’s much more to come, including stories involving Mick Jagger and the Rolling Stones, performing at the legendary Moulin Rouge and moving to Montreal and becoming (of all things) a model for the wholesome Simpsons catalogue. There are also plenty more stints in jail, for everything from grand theft auto to illegal immigration. And then there’s her entrée into more serious theatre; her recreation of her first audition, which she did without a headshot, resume or sheet music, is one of the show’s funniest set pieces.

What Caldwell leaves out of the chronology, however, is her actual transition, which she’s said in interviews was supported by her mother and some friends. It results in a dramatic gap that makes her later revelations about her personal life less effective. I have a feeling this Guide will continue to evolve; Caldwell has lived so much life that her show could even extend from one act to two.

Director Weyni Mengesha enhances the show with her glittery yet classy staging. Anahita Dehbonehie’s set evokes nightclubs, with the four-person band (led by Michael Shand) to the left, the classic black stool in front, and a backdrop that resembles an oversized fan that lights up with archival images from Caldwell’s past (Frank Donato is the video and projection designer).

There’s also a runway down the middle of the stage that allows for some lively scenes in which Caldwell, Deriveau and Miss Niki Nikita instruct us on the art of burlesque and ballroom competitions. (For the latter there’s an opportunity for audience members to jump onstage and strut their stuff.) And while there’s traditional raked seating for much of the theatre, the front section features cabaret-like tables, complete with faux candlelight that – in Michelle Ramsay’s lighting design – contain a few surprises.

The two other performers provide excellent support in bringing Caldwell’s unique story to life, and besides providing backup vocals to the show’s original songs – all but two written by Caldwell and James Dower – they each get an entertaining solo number.

There’s never any doubt, however, about whose story this is. Caldwell, exuding both strength and vulnerability, recounts her life with frankness, generosity and a bountiful spirit. Her amber-hued voice is magnificent, and her physicality a master class in grace and poise.

On opening night, as she worked her way up to the present day in her story and explained the significance of her show’s title, her eyes welled up with tears. So did those of many in the audience.

Now that’s realness.

In the interest of consistency across all critics’ reviews, The Globe has eliminated its star-rating system in film and theatre to align with coverage of music, books, visual arts and dance. Instead, works of excellence will be noted with a critic’s pick designation across all coverage. (Television reviews, typically based on an incomplete season, are exempt.)

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