American Masters

- She was an artist, activist, gay mother, and mentor to hundreds of queer and gender non-conforming youth over the years.

She starred in the fabulous 1968 drag documentary, "The Queen," alongside Ms.

Crystal LaBeija.

And she was full of life and advice for her many mentees, including her reminder that normal is just a setting on the dryer.

Her name was Flawless Sabrina and she was even once hired as a consultant to one of the most famous cowboy movies of all time, the 1969 classic "Butch Cassidy and the Sundance Kid."

I'll explain.

(upbeat music) Hi y'all, I'm Peppermint, New York City's delightful diva, and welcome to Masters of Drag, where we're telling you stories of American drag pioneers.

- [Sabrina] My name is Jack.

Well, my mother calls me Jack.

Everybody that cares about me calls me Jack.

That's my name, but I work under the name of Sabrina, and all the queens all call me Sabrina.

- Before there was Flawless Sabrina, there was Jack Doroshow, the man behind the familiar Kabuki eye makeup and coifed blonde wigs.

Doroshow was born in 1939 in Philadelphia, Pennsylvania.

He often recounted that growing up in South Philly as a gay kid of mixed Jewish and Italian descent was really hard.

In his late teens, he started studying psychology at the University of Pennsylvania, but his life changed forever during a trip to Manhattan with his friends in the late 1950s.

It was on this trip that Doroshow went to his first drag show after being invited by two queens from Pittsburgh who were staying at the same YMCA.

At the performance, the thing that shocked Doroshow most wasn't the men in stilettos and sequins.

It was the fact that the place was packed and that everyone happily paid the $5 entrance fee, which was kind of pricey back then.

When he got back to Philly, Doroshow and his two friends staged their very first drag pageant in 1959.

The men hosted the event wearing suits and although they managed to pull it off, they soon felt like outsiders to their own party.

At the second pageant Doroshow threw, he brought in a drag performer to host the show instead, and it was a huge success.

That's when Doroshow realized he needed to step it up and Flawless Sabrina was born.

Doroshow was just 19 or 20 at the time, but soon assumed the look and the mannerisms of a middle-aged Jewish lady.

She was meant to be a non-competitive mother, or even a grandmotherly figure to the other queens.

I just wanna remind you that Flawless Sabrina was throwing pageants at a time before drag was mainstream.

She realized early on the commercial value of drag and used her earnings to support her own mother and grandmother.

She was also doing it when cross-dressing was still illegal and was arrested dozens of times during the shows.

Despite this, her empire grew, and the contest soon became known as the Miss All-America Camp Beauty Pageant, a series of drag competitions held around the country that culminated each year in a national show.

The great drag documentary "The Queen" documented the 1967 nationals, when crystal LaBeija contested the winner and wasn't shy about expressing her displeasure to Flawless Sabrina on camera.

- I have a right to show my color, Dolly.

I am beautiful and I know I'm beautiful.

- Now, wait a second, hold it.

There's a party after here.

Every one of the judges is gonna be there.

You may feel perfectly free.

I'll cart you over myself and you can talk to each one of them.

- Years later, Sabrina addressed LaBeija's epic outburst, saying, "It was a difficult time to be a queen, "and maybe her drama was part of the action."

She also noted LaBeija's contributions to the world of drag in forming her own house and her vast community organizing efforts.

Looking back on that time, Sabrina remembered the mid sixties as a magical moment in American history filled with political upheaval.

She told the Village Voice in an interview that the country was young demographically, so the draft sending all those kids to the killing fields caused America to start questioning the status quo.

Once that happened, black and gay rights became part of the inquisitive collective.

Sabrina was at the center of it all.

At the height of Miss All-America, she was employing roughly 100 workers, which likely made her the largest employer of queer people in the country in the sixties.

After the 1968 premiere of "The Queen" at the Cannes Film Festival, Sabrina helped with distribution and PR, and quickly learned the ropes of filmmaking.

She left pageants behind, hosting her very last one at the famous gay resort, Fire Island Pines, in 1969, and said hello to Hollywood instead.

She quickly became known as an expert in homosexuality in the film industry and used her skills to consult on several Hollywood films.

"Butch Cassidy and the Sundance Kid" was one of them.

Sabrina was brought in to make sure that Robert Redford and Paul Newman's characters didn't appear too gay.

Just gay enough.

She didn't stop there.

It's impossible to pigeonhole Sabrina into one art form or performance style.

She did it all, baby.

For a while in the eighties, Sabrina moved to Paris, where she was once a private investigator and fixer.

(laughs) In the late eighties, she moved back to New York to be with her partner, artist Curtis Carmen.

Sabrina then established herself firmly in the underground art scene, becoming a cultural producer, who collaborated with artists on various projects.

She was associated with everyone from Andy Warhol and William S. Burroughs, who was an ex-lover, to Jackie O. and Bobby Kennedy, who, according to Sabrina, apparently loved the girls, if you know what I mean.

Some of Sabrina's most important work was her involvement with queer youth.

She was an inspiration and mentored many trans and queer children and grandchildren in her lifetime.

Before her death in November 2017 at the age of 78, Sabrina was working on a memoir and volunteering for the Hillary Clinton campaign.

According to one of her granddaughters, Zackary Drucker, she was a self-described gender clown who had no preference for pronouns or names, just a zest for life, who encouraged everyone to be their best and most authentic selves.

Drag herstory is longer than most of us think, and we're only just beginning.

(upbeat music)