Gladys Bentley was an incredible talent on the piano and one of the few women at this time who was really boldly out and unashamed of her queer desires.

You're the Gladys Bentley.

Yeah, that's right.

Your name sounded vaguely familiar.

1958 Los Angeles, California.

What are you going to say?

We're going to try to do "Them There Eyes."

"Them There Eyes"?

Blues singer and pianist Gladys Bentley made her only television appearance on Groucho Marx's "You Bet Your Life" comedy show.

Gladys Bentley, the way that she presented herself, was usually in a tux, in a top hat - but she also had the makeup.

She's always playing with identity and presentation and fluidity.

"I have violated the accepted code of morals, but the world applauded my piano playing and song styling.

Even though people bitterly condemned my personal way of living, they still could appreciate my artistry as a performer."

Gladys Bentley was born in 1907 to a working class family in Philadelphia, Pennsylvania.

Her father was African American; her mother, an immigrant from Trinidad.

"It seems I was born different.

At the age of 9, I stole my brother's suits and began to feel more comfortable in boys' clothes than in dresses."

Early on she knew that she was attracted to women.

She didn't feel like her body represented who she was.

Her parents are concerned about her budding lesbianism.

They take her to doctors hoping to cure her, to make her a quote unquote normal woman.

We have the rise of medical experts who study the science of sex, who are introducing terms like homosexual and heterosexual, but most doctors at this time saw same sex desire as pathological.

"Some decide to take the reins of their destiny in their own hands.

That is the way I reacted to being an unwanted child."

In 1923, at age 16, with dreams of becoming a musician, Bentley ran away from home to live in Harlem, New York - then the epicenter of the Harlem Renaissance.

It was a flowering time of African-American arts, letters, cultural expression.

When African Americans left the South with the Great Migration they really create lives for themselves in places like New York, Chicago, Detroit.

Building these urban communities that were tolerant, that supported experimentation and different kinds of identities.

One of the reasons Harlem emerges as such a central site for queer African Americans at this time is because this is the Prohibition Era.

So from 1920 to 1933, it is illegal to purchase alcohol, but of course we have the emergence of speakeasies where people are able to purchase bootleg alcohol and take part in other illicit activities, from gambling to interracial dancing or same-sex dancing.

So the entertainment industry becomes a really important alternative for black women who really didn't have many other opportunities for work.

Bentley first worked on the Harlem party circuit, then a job opened up at a nightclub.

The club was actually looking for a male piano player.

But she insisted that this would be the perfect time for them to start using a female instead.

"My hands flew over the keys."

"What made you men folk treat us women like you do?

I don't want no man that I got to give my money to."

"When I finished my number, the applause was terrific.

I was offered work right on the spot."

Bentley soon became a headliner at various clubs and theaters.

We have clubs such as the Ubangi Club where Gladys Bentley performed, which are appealing more to explicitly queer audiences.

We have what's known as the "pansy craze" going on, this interest in queer culture that white people had in this period.

Gladys Bentley sometimes was billed as a male impersonator, showing queerness and flirting with women on stage and singing songs with lyrics that are upsetting all the cultural norms about identity.

"That big gorilla.

A woman killer.

And I ought to know."

Bentley's lyrics were known for their bold content, highlighting her cross-dressing tendencies and her feelings towards women.

She was not the only person who cross-dressed.

Ethel Waters did it, Marlene Dietrich did it.

Women, in their own ways, were challenging conceptions of what a woman could be.

Gladys Bentley represents this lyrical and sexual prowess that women like me can wear on stage, that is not ladylike.

My name is Shirlette Ammons.

I am a musician, writer and television producer.

Just knowing that Gladys existed and existed so proudly and so openly changed my life and completely gave me license to be all the things that I am: black, Southern, queer, an artist .

And so I started writing this record called Twilight for Gladys Bentley to reimagine Gladys in the body of a hip hop artist.

Gladys used the popular music of her time to make a statement.

I use the popular music of my time to make a parallel statement.

In 1928, Bentley began a recording career that would span two decades.

She traveled to clubs all over the country and inspired characters in several books.

"The clubs where I worked overflowed with celebrities.

I had made my mark in show business."

But beyond the world of show business, Bentley's lifestyle faced criticism.

There was really no way that someone like her could be viewed as a respectable figure at this time.

This is the Jim Crow era, right?

There's such a concern about racial uplift, upward mobility, that a figure such as Bentley is seen as so deviant that many in the mainstream African American community were not a fan, to put it mildly.

There were people such as Adam Clayton Powell or traditional mainline churches that had views of homosexuality that did not fit the tenants of Christian beliefs.

And for many people it was an aberration, something going against what God dictated.

And so that backlash existed.

Bentley's act fell on hard times in the mid 1930s.

The Depression definitely made a difference in the entertainment world.

And with the end of prohibition, we actually see more regulation of nightclub spaces.

There's a concern about bar spaces that are seen as disorderly, and disorderly was often a code word for gay at this time.

In 1937, Bentley moved to Los Angeles, California.

But there she faced challenges to her desire to perform on stage in men's clothing.

The state of California actually had anti-cross-dressing laws that went back to the 19th century to keep entertainment good and clean.

And there were times where she was banned from performing because of her cross-dressing.

In the early 1950s, Bentley adapted her public image to match the times.

The post World War II era becomes incredibly conservative, especially around norms of gender and sexuality.

And this leads to what is known as not only the Red Scare but also the Lavender Scare, and this kind of comes to a head with the firing of hundreds of government employees who are thought to be gay.

And possibly as a reaction to those times, she had to change her performance style to stay employed and to keep doing her line of work.

This is when we see her publish an article in Ebony magazine with the title, "I am a Woman Again".

"For many years, I inhabited that half shadow no man's land which exists between the boundaries of the two sexes... Today I am a woman again through the miracle of modern medicine, living a normal existence."

In that same article, Bentley stated that she consulted a doctor to receive hormone treatments, and also married a man.

I think she is spinning a tale of respectability, right?

A tale of someone who wants to be seen as fully human in this very repressive time.

If you read that article really closely, it really is a plea for tolerance and understanding.

She's not condemning who she was or is, but really explaining the struggles of what it meant to live her life.

She went back into the closet so that one day I would never have to do that.

But this is a white boy's game still.

When you're making music that represents a marginalized history and the gatekeepers still don't look like you, that's something that a lot of musicians and artists who are black, are queer, are constantly battling.

Bentley was studying to become an ordained Christian minister when she died of complications from a flu virus at age 52.

I see her as a pioneer.

She's somebody we could all look up to - whether we're gay, lesbian, bi, heterosexual.

She invited us to be our whole selves and that's what we all want to be."

"I have earned the distinction of being the first, and in some cases, the only performer of my race to crash the most plush glitter spots.

I am still a star."