Gladys Bentley

Summary

Stuff You Missed in History Class — Episode Summary

Episode Title: Gladys Bentley
Podcast: Stuff You Missed in History Class (iHeartPodcasts)
Date: April 6, 2026
Hosts: Holly Frey & Tracy V. Wilson

---

Episode Overview

This episode dives into the life and legacy of Gladys Bentley, a trailblazing Black performer who gained fame as a pianist, singer, and entertainer in the Harlem Renaissance. Known for her gender-bending style, her frank and bawdy lyrics, and her open lesbian identity at a time of intense societal repression, Bentley’s story is both glamorous and fraught with challenges. The hosts examine not just her rise to stardom, but also the contradictions, controversies, and struggles—especially surrounding her sexuality and public persona—that marked her career and later life.

Content warnings:

• Discussion of repression and erasure of sexual identity (self and familial)
• Brief mentions of police brutality, abuse, and sexually explicit song lyrics

---

Key Discussion Points & Insights

1. Early Life & Identity

• Birth and Family Background (04:24)
  • Gladys Alberta Bentley was born August 12, 1907, likely in Philadelphia, although one interview claimed Trinidad.
  • Her mother Mary was from Trinidad; father George from Philadelphia. Family quickly established in Philadelphia.
• Childhood Rejection & Gender Nonconformity (05:23–07:15)
  • Bentley’s mother desperately wanted a boy and refused to care for Gladys after birth; raised by grandmother for six months.
  • Gladys recounted not liking men from an early age and disliked her brothers due to perceived family favoritism. She also began wearing their suits at age 9 or 10.
  • Quote:

    "That is the way I reacted to being an unwanted child." — Gladys Bentley (05:23, cited by Holly)

  • Developed early crush on a female teacher; parents attempted “conversion therapy” via doctors, though Gladys believed she needed love, not medical intervention.

2. The Harlem Renaissance and Early Career

• Context: The Wales Padlock Law & Queer Performance in NY (08:58–09:56)
  • 1927: Law allowed NYC police to shut down venues featuring “indecent” or queer entertainment.
  • Enforcement focused on Broadway/theater district, enabling a queer scene to flourish in Harlem.
• Bentley’s Rise in Harlem (15:00–18:28)
  • Started playing rent parties: boisterous events in private homes to raise money for rent, with jazz, dancing, and illegal alcohol during Prohibition.
  • Signature “eight to the bar” piano style—unique, fast, and upbeat—set her apart.
  • Quote:

    "Gladys was the original." — Rob Roy in 1955 (15:54, cited by Tracy)

  • Gladys performed in dandy style—white tuxedo & top hat, short slicked hair. She dressed this way off-stage as well; lived as a woman but presented as a “drag king” before the term existed.
• Success and Celebrity (18:28–21:17)
  • Secured agent and $400 recording deal; soon commanded $125/week at Harlem’s most popular clubs, which even renamed themselves for her.
  • Appealed to diverse crowds; moved to luxury Park Avenue apartment, drove high-end cars, and became a celebrity in the Black and queer community.

3. Scandal, Police Raids, and Legal Troubles

• The Clam House, King’s Terrace, and Padlock Law Enforcement (21:17–24:19)
  • Gladys’s exclusive contracts led to legal disputes as she sought mainstream midtown bookings.
  • Notable scandal: At King’s Terrace, she performed with drag backup singers and explicit parodies, leading to complaints and police raids under the Wales Padlock Act.
  • Host reads from outraged contemporary newspaper accounts describing the “vile” “lewd entertainment.”
  • Quote:

    "A chorus of eight liberally painted male sepiens… assisted the singer in throwing this piece of filth at a blushing audience." (24:19, quoting Deputy Police Commissioner)

4. Bentley’s Public Persona, Gender, and Sexuality

• Continued Defiance & Mystery Marriages (26:19–27:19)
  • Continued performing in Harlem post-scandal; claimed a marriage to a white woman (unverified and probably illicit if true).
  • Songs often covered harsh realities of heteronormative relationships and domestic abuse.
  • Quote:

    "I was an angel he was born to treat me right who the devil heard of an angel that gets beat up every night. How much of that stuff can I stand?" (27:19, lyrics from "How Much Can I Stand")

• Changes in Style/Decline of Career (28:47–29:37)
  • Over time, changed her performance style—less raucous, more refined, which impacted her audience draw.
  • The Great Depression also led to club closures and fewer opportunities in Harlem.

5. West Coast Move and Survival in a Hostile Era

• Relocation and Legal Restrictions in California (34:10–35:36)
  • Moved to LA in the late 1940s, but audiences less receptive, and gender nonconformity more tightly policed.
  • At venues like Joaquin’s El Rancho, had to get special police permit for wearing pants.
  • Club advertisements sometimes focused on her physical appearance or novelty status, undermining her artistic gravitas.
• Public “Straight-Washing”: The Ebony Article (35:36–41:52)
  • 1952: Gladys published "I Am a Woman Again" in Ebony, claiming a “miracle” via hormone therapy had made her heterosexual and led to marriage with a man.
  • Narrative fits 1950s anxieties (see: Lavender Scare). Later, the “husband” JT Gibson was publicly denied as such posthumously, leading to confusion:

    "I am not and have never been married to Gladys Bentley. I'm going to sue the blank magazine…" — J.T. Gibson via Maceo Sheffield (37:25, recounted by Holly)

  • The article included stylized “domestic” photos of Gladys in dresses, doing housework—an abrupt turn from her known life.
  • Most contemporary scholars see this as a sad but understandable attempt to preserve her career and safety.

6. Final Years and Legacy

• Last Known Marriages and Obscurities (43:42–44:16)
  • Married Charles Robert, a Sacramento cook, in 1952, but little is known, leading to speculation the marriage was for show.
• Unpublished Memoir, Final Performances (44:16–45:15)
  • Wrote but did not publish autobiography "If This Be Sin." Only known film footage: 1958 "You Bet Your Life" appearance with Groucho Marx, where her musical talent and charisma shine.
• Death and Aftermath (45:15–45:44)
  • Gladys died of pneumonia on February 8, 1960, age 52, living with her mother, who later was buried beside her.

---

Notable Quotes & Memorable Moments

• On Childhood Alienation:

  "Many of us who have strayed from the paths of what society calls normal were once children in unhappy or broken homes... Some children become aggressive, decide to take the reins of their destiny in their own hands. That is the way I reacted to being an unwanted child." — Gladys Bentley (05:23, via Holly)

• On Performer Authenticity:

  "Gladys, you know, not always a reliable narrator of her own life." — Holly Frey (05:23)

• On Style and Transgressiveness:

  "She dressed in menswear all the time, and she was as flamboyant and bawdy offstage as she was on." — Holly Frey (16:58)

• On the Ebony Article’s Contradiction:

  "This entire article seems like such a departure from the life Gladys Bentley lived in the years prior that it seems confusing and almost shocking. But this is also an instance where context really, really matters." — Holly Frey (41:52)

---

Key Timestamps

• 04:24 — Gladys Bentley’s birth, family background, and conflicting birthplace claims
• 05:23–07:15 — Childhood rejection, early gender nonconformity, parental attempts at conversion
• 08:58–09:56 — The Wales Padlock Law and state repression of queer performers
• 15:00–18:28 — Rise to Harlem fame, “eight to the bar” piano playing, dandy persona
• 21:17–24:19 — Police raid at King’s Terrace, contemporary condemnation, closing under Padlock Act
• 26:19–27:19 — Bentley’s claimed (unverified) marriage to a woman, continued defiance
• 34:10–35:36 — Move to California, increased policing of gender, problematic club advertisements
• 35:36–41:52 — The 1952 “I Am a Woman Again” Ebony article and its surrounding controversies and speculations
• 44:16–45:15 — Bentley’s unpublished memoir and rare TV performance
• 45:15–45:44 — Bentley’s death; legacy

---

Tone and Language

The episode balances humor and empathy, classic to Stuff You Missed in History Class, with candid recognition of the injustices Bentley endured. Holly and Tracy frequently examine sources critically, point out where history is ambiguous, and clearly note when contemporary values or vocabulary don’t neatly fit Bentley’s experiences. Their admiration for Bentley’s courage, style, and talent is evident throughout.

---

For Listeners: Why This Episode Matters

Gladys Bentley’s story is a vivid reminder of queer history’s complexity, the courage of those who broke barriers, and the ways societal pressures can erase or rewrite lives. The hosts blend narrative, cultural critique, and primary sources to illuminate both Bentley’s stardom and her struggles—making this an essential listen (or read!) for anyone interested in the intersections of race, gender, sexuality, and American musical history.

Transcript

[Tracy V. Wilson]

This is an I Heart Podcast, Guaranteed human brought to you in part by Vital Farms. I love eggs. I turn to them all the time as a quick and easy way to start a meal. And Vital Farms eggs are brought to you by hens that have access to fresh air and sunshine and you can actually look up on the carton and see the farm that those eggs came from. Vital Farms is also a certified bee corporation with a purpose to improve the lives of people, animals and the planet through food. We look for the black egg carton in the egg aisle and visit vitalfarms.com to learn more. Vital Good Eggs no shortcuts Wouldn't it

[Holly Frey]

be great to never buy gas again? EVs are as easy to charge as your phone and they are a perfect addition to your everyday life. Most people are only driving about 40 miles a day and most EVs can handle 200 to 400 miles of range on a charge. And there are hundreds of EV models available today, so there's something perfect for every lifestyle and budget. I drive an ev. I've had it for a couple of years. It's my favorite car I ever owned. It is so fun to drive. The pickup is incredible. It's super agile and it is easy to maintain. The way forward is electric. Learn more at electricforall.org @BritBox Character is

[BritBox Announcer]

Everything Stream the iconic characters defining British TV on BritBox, including Ludwig.

[Tracy V. Wilson]

I think I might just have solved a murder, Vera.

[Holly Frey]

Now we're getting somewhere.

[BritBox Announcer]

Agatha Christie's Poirot and more more beloved

[Holly Frey]

favorites I'm a Policeman, I'm a Professional,

[T-Mobile Advertiser 1]

I'm a Time Lord, I'm the Duchess of York.

[BritBox Announcer]

Once you know them, you never quite forget them.

[Holly Frey]

I ain't being vain.

[T-Mobile Advertiser 1]

I just am special.

[BritBox Announcer]

Stream the best of British TV on BritBox. Watch with a free trial today at

[Kohler Ambassador]

BritBox.com when Kohler, Global Design leader in luxurious kitchen and bath products, asked me to be their ambassador for timeless, elegant, durable cast iron, I said, I'm in. Soon after, I was in their Kohler Wisconsin foundry watching molten iron, poured enamel applied by hand, and the beautiful finished pieces ready to ship. Since 1883, Kohler cast iron has been crafted by incredible artisans, and seeing it firsthand gave me a whole new appreciation for their craftsmanship. Now I'm proud to lend my stamp of approval to my favorite Kohler cast Iron products from for their durability, beauty and enduring style. Shop my curated [e-mail] as the Kohler Cast Iron Ambassador, I say long live Cast Iron.

[Holly Frey]

Welcome to Stuff youf Missed in History Class, a production of iHeartradio. Hello and welcome to the podcast. I'm Holly Fry.

[Tracy V. Wilson]

And I'm Tracy V. Wilson.

[Holly Frey]

So today's topic was part of the Harlem Renaissance. As a musician, she played piano and she sang in ways that drew huge crowds starting in the 1920s. She was unique in that she was completely out as a lesbian. Unusual for the time, but her story takes some really surprising turns. She is, when she is talked about, it's often like gay icon Gladys Bentley. But then there are some weird parts of her story that do get mentioned by people, but they don't get picked apart as much as I would like in terms of like really looking closely at them. So we're gonna do that and this one gets a couple of heads ups. So first, there are some really sad aspects of Gladys story regarding her sexual identity and attempts at its erasure by her parents and even by Gladys herself. If that sounds painful to you, just be prepared. Or maybe skip because that was part of an article that she wrote about herself in the 1950s. That article has been questioned when it comes to whether she was purposely trying to redact her queerness as a self protective ruse. Like I said, we're going to pick that apart when we get to it. There is also a very brief mention of police brutality and there are very brief discussions of song lyrics about domestic abuse. One also about a sex act. Those are all very quick though, so just know those are in the episode. If those are things you might be sensitive to or if you have a younger history buff that listens, you might want to prescreen.

[Tracy V. Wilson]

From the very beginning, Gladys Alberta Bentley offers us some contradictions. She was born on August 12, 1907. Her. Her place of birth is almost always given as Philadelphia and that includes in obituaries. And she did grow up in Philadelphia. But during an appearance on the television show you Bet yout life in 1958, Groucho Marx asked her where she was from and without any hesitation she said Port of Spain, Trinidad. Her mother Mary was from Trinidad and her father George was from Philadelphia. If she was actually born in Trinidad, it seems like the family must have moved to Philadelphia when she was very young. She always talked about her childhood as taking place in Philadelphia exclusively and never apparently mentioned anything about Trinidad publicly outside of this one mention on one TV show

[Holly Frey]

just starting it out. Gladys, Gladys, you know, not always a reliable narrator of her own life. She would write of her childhood many years later, later, and how difficult her relationship with her mother was as a kid. She wrote, quote, many of us who have strayed from the paths of what society calls normal were once children in unhappy or broken homes. Children who are rejected, abused, unloved, exploited, or overprotected do not have a chance to develop that inner sense of security which will keep them from feeling abandoned and afraid. However, not all children in situations of this nature react by feeling alone or fearful. Some children become aggressive, decide to take the reins of their destiny in their own hands. That is the way I reacted to being an unwanted child. So she continues to recount how her mother really had her heart set on having a boy. She wanted a boy. She wanted a boy so much that when she learned she had given birth to a girl, she actually refused to nurse or even touch the baby. And for the first six months of her life, Gladys was raised by her grandmother.

[Tracy V. Wilson]

Gladys also described not liking men from the time she was very young, noting, quote, from the time I can remember anything, even when I was toddling, I never wanted a man to touch me. I would even run away from my own father. He felt terrible about his own child, avoiding him, but I would never go to him. I acted the same way with my uncles and all the rest of the males who came into my home. She also described hating her two brothers because they were celebrated while she was scorned. And she said that she started stealing their suits to wear when she was 9 or 10. And her parents got very upset about that.

[Holly Frey]

Yeah, also her. She ended up with more brothers than that, but I think she had two that were born immediately after her that were closest to her in age. Gladys described herself as a large and stocky child. Those are her precise words. And it was something that other kids frequently teased her about. She later told the press that she started writing songs when she was 8 years old just to keep herself company because she was lonely and outcast among other kids. But that was not the only thing that set her apart from her peers. She also found herself developing a crush on her teacher, noting, quote, in class I sat for hours watching her and wondering why I was so attracted to her. At night I dreamed of her. It's unclear if Gladys parents knew about this infatuation with her teacher, but it does seem that they understood, at least on some level, that Gladys did not align with the heteronormative social mores of Philadelphia. The family soon moved to another neighborhood, but still in the city, and Gladys mother started taking her to a series of doctors. Biographers have interpreted this situation as attempts at conversion therapy. She noted later that she Believed that her parents meant well, but that she didn't need a doctor. She needed love and affection. Though she and her parents did try to come to compromises on things like her wearing non frilly girl's clothes instead of her brother's suits. As Gladys reached her teenage years, things at home just got worse and she ran away at 16 to New York, hoping to find a career as a performer.

[Tracy V. Wilson]

In 1927, New York passed a piece of legislation known as the Wales Padlock Law. This was in response to Manhattan's growing community of performers. And a lot of those performers were queer and were pushing against the boundaries of propriety to explore stories and music that mainstream audiences and the authorities thought were indecent. One of the last straws that catalyzed the Wales Padlock law was Mae West's play Sex, which she starred in and also wrote under the pen name Jane Mast. That play was raided and soon Senator B. Roger Wales had sponsored an amendment to the penal code that regulated indecent materials to include, among other things, a provision that the police could just shut down an establishment that was staging purportedly indecent or sexually degenerate entertainment and then literally padlock it shut for up to a year.

[Holly Frey]

So this is the New York that Gladys started her career in. And that law meant that a lot of the material that she would eventually perform and become really well known for could get her into trouble. But over the years, as we'll see, she stayed booked and crowds continued to show up to hear her play piano and sing her often very raunchy songs. One of the main reasons for this was just a matter of location. The police tended to focus on Broadway in the theater district. And at that point, Gladys was playing venues in Harlem. The law still applied there, but it was not really enforced that far north in the city. And as a consequence, a vibrant queer culture flourished. Drag balls and drag performances were common and Bentley, as a cross dressing out lesbian, became a star.

[Tracy V. Wilson]

We'll talk about how Gladys Bentley got started in New York after we pause for a sponsor break.

[Holly Frey]

Recently, True Nature Meats sent me some of their buffalo chicken breast and I had some with mashed potatoes and blue cheese. After I just heated up the chicken really quickly in the skillet and then I used the leftover chicken in a chicken salad. And let me tell you, that was one for the history books. Head to TrueNatureMeats.com history get 20% off plus free New York strip, Brazilian garlic beef and Mediterranean chicken. Won't last long. TrueNatureMeats.com history. I'm hooked. You will be too. Unlike the people we normally talk about on the show, we are living in a time when Internet connectivity is a standard part of life for most people and there is literally no way we could research and prepare our podcast without the Internet. If connectivity goes down for me, it can be really hard to make up that lost time. And for businesses, Internet connectivity is even more of a necessity. Spectrum Business keeps businesses of all sizes connected seamlessly with fast and reliable Internet, advanced wi, fi, phone, tv and mobile services. Spectrum business offers 100% US based customer support and they do it 24 7. That means you can always stay up and running no matter what hours your business keeps. Spectrum Business also will tailor connectivity solutions just for you. They will put a package together that is built for your business budget. Millions of business owners rely on Spectrum Business to keep them connected. So visit spectrum.combusiness to learn more. Restrictions apply. Service is not available in all areas. Some British TV characters are so iconic, they feel larger than life. Take Hercule Poirot, Agatha Christie's meticulously groomed detective whose mustache has a personality of its own. Or David Brent from the Office, a man who turned workplace awkwardness into a study in secondhand embarrassment. Britbox has the characters you simply won't be able to get out of your mind. Ludwig charms as the brilliant yet offbeat puzzle maker turned accidental detective Jane Andrews captivates in the lady, inspired by the true story of the royal dresser whose fairy tale ended in scandal and murder. And of course, the Mitford sisters show us how to stir up controversy in Outrageous, based on one of Britain's most notorious families. If you like your characters clever, complicated and occasionally infamous, you might have just found your next rabbit hole on Britbox. Start watching with a free trial [e-mail].

[T-Mobile Advertiser 2]

Hey, Donald, really flying on that treadmill.

[T-Mobile Advertiser 1]

I'm trying to run as fast AS T mobile 5G home Internet.

[T-Mobile Advertiser 2]

Zach. Well, you better pick it up because now T Mobile has the fastest 5G home Internet according to OOKLA Speed Test.

[Holly Frey]

Really?

[T-Mobile Advertiser 1]

How's this?

[T-Mobile Advertiser 2]

T Mobile's faster than that, bud. Speed up.

[T-Mobile Advertiser 1]

No.

[T-Mobile Advertiser 2]

Plus they've got a five year price guarantee. Come on. Faster.

[T-Mobile Advertiser 1]

How can I go any faster?

[T-Mobile Advertiser 2]

Channel the speed of t mobile 5G home Internet. Think 100 meter dash fast. Think drag racing fast. Think speed skating fast. Now let's bump up your speed a notch.

[T-Mobile Advertiser 1]

Hey, whoa, whoa. That's too fast.

[T-Mobile Advertiser 2]

You'll be alright. Just walk it off.

[T-Mobile Advertiser 3]

Get on the fast track. T Mobile now has the fastest 5G home Internet. And for a limited time it starts at just 30 bucks a month with autopay and a voice line plus a five year price guarantee plus taxes and fees.

[T-Mobile Advertiser 4]

Fastest according to Ooklo Speed test intelligence data. Second Half 2025 all rights reserved guarantee for monthly price of 5G. Internet data on eligible plans. Find exclusions and details@t mobile.com.

[Holly Frey]

Gladys Bentley is often talked about for being transgressive. But she wasn't just transgressive, she was also incredibly talented. When she got to New York, she started performing at rent parties in Harlem in the mid-1920s. So just as the Wales padlock law was coming into play, so a rent party was, as its name suggests, a way for tenants to raise the funds needed to pay ever rising rent costs. For a small door charge, people could join the party and then they also paid for drinks. Prohibition was in effect from the beginning of 1920 to the end of 1933. So the alcohol served at these parties was home brewed and to draw crowds, musicians were booked to play. And these parties became these really boisterous community events where people would gather, drink and dance. And it was all within the confines of a private residence. Sometimes in places like Brownstones, multiple units would hold the party at the same time. So it got to be this immense house party. Innovations in jazz and dances that would become popular on the swing scene in the decades that followed came directly out of these neighborhood gatherings and Bentley was a very popular draw.

[Tracy V. Wilson]

Gladys became well known for performing songs in what was known as eight to the bar style, meaning unlike the more standard four beats per bar of music, each bar would get eight beats. So a very fast up tempo style. If you are a musician or if you talk to a musician about music theory, there's a way more complex discussion about how this can be represented in time signatures and what actually comprises a bar of music. But for a layperson, what you need to know here is this was just a very fast, super upbeat style. In 1955, Rob Roy wrote an article about what made Bentley's performances stand out and that was their uniqueness. Nobody was really doing this eight to the bar style. Aside from some copycats. Roy said that the trade, that being the theater district around New York's Broadway and 52nd Streets, quote, preferred listening to the original, and Gladys was the original.

[Holly Frey]

In addition to being very skilled at uptempo playing and singing, Gladys was also a very clever lyricist and she would improvise new words to popular songs. Often her new verses were very dirty. In contrast, though, to her bawdy lyrics. She dressed like a dandy. She usually performed in a white tailored men's tuxedo and a white top hat. She wore her hair very short in what would be considered at the time a very masculine cut. She normally had it slicked back. And this combination of highly polished visual presentation, her musical talent, and her very naughty lyrics made her just irresistible to audiences. And she didn't confine this Persona to performance only. She dressed in menswear all the time, and she was as flamboyant and bawdy offstage as she was on. She self identified as a woman, and she's often referred to as a drag king in modern discussion. But the term drag king didn't really exist for almost a half century after this. She was also not putting on this Persona just for performance the way a lot of drag artists do, although her promoters did often bill her as a male impersonator. So it's all a little bit tricky here. As is always the case when we're talking about someone who was queer before the terminology that we would use today existed. It is hard to know precisely how Gladys would identify today.

[Tracy V. Wilson]

Buoyed by her popularity, she got an agent, and the agent got her a record deal for eight recorded songs. She got $400, which she was very excited about, but she knew she could not live off of that forever. So she also started going to music clubs and bars that had musical acts. She would basically ask if she could play. When the build musicians were on their breaks, she would just play for tips while other people were having downtime. Then she got a lead on a piano player opening at a club called the Madhouse, and she went for an audition. The club wanted a male player, but when Gladys showed up, they let her play a set and the audience really loved her. And she said that after her first song, a white man handed her a $5 tip and said, quote, please play something else. We don't care what it is, just play. You're terrific. Bentley was hired on the spot, making $35 a week. In those early days, she went by the stage name Barbara Minton or Bobby. And her act became so popular that she drew huge and diverse crowds. Black and white customers alike flooded into the club. Her pay was soon raised to $125 a week plus tips. She was such a draw that the club changed its name to Barbara's Exclusive Club so that everybody in the city knew where to find her. A 1949 write up by Bill Chase for the New York Age, recalling the exclusive club, noted, quote, the Dynamite. Gladys Bentley used to draw celebrities like flies to syrup.

[Holly Frey]

From there, Gladys got bookings all around Harlem, including a long run at a place called the Clam House. This was a very well known speakeasy that catered to the queer community, although straight people also flocked to it just to hear Gladys's shows. And she started making a lot of money because as Tracy just said, she appealed to audiences across just about every demographic. As a consequence, she was able to move into a luxury apartment on Park Avenue and she had a full staff there. She also talked about driving a very nice car. For a while. She had a live in romantic partner named Beatrice Robert. In 1932, celebrated black cartoonist E. Sims Campbell, who is on my short list if I could find enough material to research for it, created this gorgeous illustrated map of Harlem's nightlife in pen and brush. And this piece, which is now in the collection of Yale's Benneke Rare Book and Manuscript Library, features as one of the locations the Clam House. It is labeled as Gladys Clam House. And you can see the performer drawn seated at the piano and playing. And then there's lettering next to this part of the map that reads, Gladys Bentley wears a tuxedo and high hat.

[Tracy V. Wilson]

In Walter Winchell's gossip column on Broadway in February 1933, there is just a one line mention of Gladys and that reads only quote, gladys Bentley's penthouse on West 54th is so naughty. While there are zero details conveyed about exactly what that means, it indicates that she was well known enough to make a gossip column with no explainer needed of who she was. She was so popular that she was also getting bookings in midtown Manhattan. But this got her into legal trouble with Harry Hansberry and Matt Palin, who were the owners of the Clam House. They had a multi year contract with Bentley and had made the club all about her and her act. So for her to start taking bookings somewhere else, they said was a breach of her contract. As legal maneuvering dragged on with this, Gladys took other bookings anyway. And that led to different legal problems.

[Holly Frey]

In 1934, Gladys was performing at a club in midtown Manhattan known as King's Terrace. She had several drag queens performing with her as backup singers. And she performed songs with lyrics that some audience members found quite shocking. One song that she sang pretty often was a riff on the song Alice Bluegown, which was written by Joseph McCarthy and Harry Tierney for the musical Irene. And while the original song is a very sweet and innocent number about a dress, that is Alice Blue Inspired by the color of a dress worn by Alice Roosevelt. If you want to hear the original, there's a beautiful Judy Garland recording. Uh, but Gladys version switched up the lyrics to make this song about anal sex. Uh, and she would often encourage the audience to sing along with her, which a lot of people did, and they loved this irreverent act. But some of them were downright scandalized and they reported Gladys to the authorities. Uh, this was the year immediately following the end of Prohibition. And as police were no longer kept busy trying to hunt down illicit alcohol operations, they turned their attention to the perceived problem of indecency. And that meant that they started raiding gay clubs and clubs where gay people performed. So King's Terrace became a target.

[Tracy V. Wilson]

One newspaper article about this opens with kind of a run on sentence. Quote, with the New York City New Deal in city government under the aegis of mayor Fiorella H. LaGuardia comes at last the secret police campaign to clean up the nightlife and cabaret entertainment. It was revealed Thursday when Harold L. Allen, second deputy police commissioner, ordered almost 30 managers and entertainers to appear before him to explain irregularities ranging from violation of the curfew to presentation of lewd entertainment. And so reform came at last, as it must to all, one supposes, to Gladys Bentley, race entertainer at the King's Terrace.

[Holly Frey]

So this article went on to quote Harold L. Allen describing what police saw when they raided the club. Quote, we have received complaints that the entertainment in certain places is vile and we have investigated. I am not easily shocked, but some of these shows are certainly vile and they should not continue. So he talked about the various clubs that had been investigated, and then he described Gladys act. Quote. Following a commonplace song, Gladys Bentley begins a number entitled There's a Hell of a Situation up at Yale, which is followed by a scene worthy of a Northwestern stag lumber camp song fest. A chorus of eight liberally painted male sepiens with effeminate voices and gestures assisted the singer in throwing this piece of filth at a blushing audience. The chorus men were dressed in vivid satin pajamas, only slightly less extreme than the colors of their faces. The chief and filthiest offering of the evening, however, is a personal tour of the tables by Ms. Bentley. At each table she stopped to sing one or more verses of a seemingly endless song in which every word known to vulgar profanity is used. This sounds like the parents in Footloose that don't want dancing to happen. He's just so worked up. Allan then stated that the entertainment was so offensive that some of the audience Left and also mentioned that Gladys and her dancers accepted drinks from patrons and described this as something that would normally happen in what he called lower class clubs. King's Terrace was shut down by the police. They literally put a padlock on the door to prevent anyone from entering. They, of course, were invoking the Wales Padlock Act. Incidentally, just for clarity, because you might be wondering, the issue with the song There's a Hell of a Situation up at Yale was that that song is about masturbation.

[Tracy V. Wilson]

Gladys continued to live her life openly, although for a while she was back to only playing in Harlem. She booked a long run at the Eubanki Club at the corner of 131st street and 7th Avenue. But the white crowds just followed her back to Harlem. She did not seem to change anything about her act or about herself. She even told the press that she had married a white woman in a civil service in New Jersey. That claim has never been verified. The woman's name has never been known. Same sex marriages would not have been legal. So if Gladys and a woman did get married, if they did find a judge willing to marry them, that almost certainly would have required a deception to suggest that one of them was a man. Gladys probably could have pulled that off, but she was also really well known, so she probably would have been recognized. Unless it was a really clueless judge who wasn't aware. This one remains kind of a history mystery.

[Holly Frey]

Yeah, nobody has ever figured out if there was really a woman, if they had maybe a service that wasn't a legal service, like what may have gone on. Just big question marks. Eventually, that King's Terrace scandal was all but forgotten and Bentley started getting booked in Midtown again. She headlined at Tondaleo's in Midtown as well as other venues. She still had her rich alto voice and its range that passed from these low, growly segments to higher trills. She did this cool thing where she would do the higher notes through like a closed mouth, through her teeth with incredible skill. It was so cool. There's a video we'll talk about later that you can see her playing was as good as ever as she banged out blues numbers. A lot of the songs that she was famous for, maybe surprisingly, in addition to those filthy ones, had lyrics that were about heteronormative relationships. Although less surprisingly, those relationships were not good. And they often featured narratives of abuse. For example, in a song called How Much Can I Stand, she sang. The lyrics said, I was an angel he was born to treat me right who the devil heard of an angel that gets beat up every night. How much of that stuff can I stand? In a similar vein, her song called Worried Blues includes the lyrics, what made you men folk treat us women like you do I don't want no man that I gotta give my money to.

[Tracy V. Wilson]

But songs like that, which she sang from the beginning of her career, continued to be part of her acting. As she got more famous, she also got more and more refined. From a production value standpoint, she hired somebody else to play the piano while she sang and the verve of her stage presence started to get a little too smooth around the edges for people. It led to a drop off in crowds. Additionally, as the Great Depression wore on, a lot of clubs started closing and that was especially true in Harlem. Still, Gladys was still being written about with glowing praise during her run at Tondelayos. Critic Alvin Moses wrote of her quote, if there is any name on our morning patrol along the Broadway Rialto that outrates Gladys Bentley as a draw, you call me up and tell me who is the owner of it.

[Holly Frey]

Gladys eventually decided to leave New York and we will talk about that and the infamous article we referenced at the top of the show after we hear from the sponsors that keep Stuff youf Missed in History Class going. Recently, True Nature Meats sent me their Mediterranean chicken breast to try. I just warmed it up in a skillet for a couple of minutes and served it as part of a meal and this chicken was wonderfully tender. It's got these great herb notes. It's really delicious and savory without being overpowering. And I love that these flavors have their own roots in history. These are the same herbs that would have been used during the times of Greek symposia and served as part of Roman feasts. It's pretty cool. You could travel through time with your palate. True Nature Meats has supplied the world's finest restaurants for more than 30 years, so they have their own unique history and odds are good that you have actually had meat that they have supplied without even knowing it. Now you can get those same delicious restaurant flavors at home for a fraction of the price. Head to truenaturemeats.com history get 20% off plus free New York strip Brazilian garlic beef and Mediterranean chicken won't last. Hurry. TrueNatureMeats.com History Worth Exploring. Unlike the people we normally talk about on the show, we are living in a time when Internet connectivity is a standard part of life for most people and there is literally no way we could research and prepare our podcast without the Internet. If connectivity goes down for me, it can be really hard to make up that lost time. And for businesses, Internet connectivity is even more of a necessity. Spectrum Business keeps businesses of all sizes connected seamlessly with fast and reliable Internet, advanced Wi, Fi, phone, TV and mobile services. Spectrum business offers 100% US based customer support and they do it 24 7. That means you can always stay up and running no matter what hours your business keeps. Spectrum Business also will tailor connectivity solutions just for you. They will put a package together that is built for your business budget. Millions of business owners rely on Spectrum Business to keep them connected. So visit spectrum.combusiness to learn more. Restrictions apply. Service is not available in all areas. Some British TV characters are so iconic, they feel larger than life. Take Hercule Poirot, Agatha Christie's meticulously groomed detective whose mustache has a personality of its own. Or David Brent from the Office, a man who turned workplace awkwardness into a study in secondhand embarrassment. Britbox has the characters you simply won't be able to get out of your mind. Ludwig charms as the brilliant yet offbeat puzzle maker turned accidental detective Jane Andrews captivates in the lady, inspired by the true story of the royal dresser whose fairy tale ended in scandal and murder. And of course, the Mitford sisters show us how to stir up controversy in Outrageous, based on one of Britain's notorious families. If you like your characters clever, complicated and occasionally infamous, you might have just found your next rabbit hole on Britbox. Start watching with a free trial [e-mail].

[T-Mobile Advertiser 2]

Hey, Donald, really flying on that treadmill.

[T-Mobile Advertiser 1]

I'm trying to run as fast AS T mobile 5G home Internet, Zach.

[T-Mobile Advertiser 2]

Well, you better pick it up because now T Mobile has the fastest 5G home Internet according to Ookla Speed Test.

[Holly Frey]

Really?

[T-Mobile Advertiser 1]

How's this?

[T-Mobile Advertiser 2]

T Mobile's faster than that, bud. Speed up.

[T-Mobile Advertiser 1]

No.

[T-Mobile Advertiser 2]

Plus, they've got a five year price guarantee. Come on. Faster.

[T-Mobile Advertiser 1]

How can I go any faster?

[T-Mobile Advertiser 2]

Channel the speed oft mobile 5G home Internet. Think hundred meter dash fast. Think drag racing fast. Think speed skating fast. Now let's bump up your speed a notch.

[T-Mobile Advertiser 1]

Hey, whoa, whoa. That's too fast.

[T-Mobile Advertiser 2]

You'll be all right. Just walk it off.

[T-Mobile Advertiser 3]

Get on the fast track. T Mobile now has the fastest 5G home Internet. And for a limited time, it starts at just 30 bucks a month with autopay and a voice line. Plus a five year price guarantee plus taxes and fees.

[T-Mobile Advertiser 4]

Fastest according to Ooklo Speed test intelligence data. Second Half 2025 all rights reserved. Guarantee for monthly price of 5G Internet data on eligible plans. Find exclusions and details@t mobile.com.

[Holly Frey]

As the 1940s wound down, Bentley headed to the west coast. And while she did get bookings there, the audiences of California were less enthusiastic about her style of presentation and music outside of New York. She had the sharp realization that not everyone was as willing to let a performer buck against social norms and basically make that the focus of their actual so she started to tone her act down, and while she still wore men's suit jackets and ties, they were more increasingly paired with skirts instead of trousers. And this wasn't just a matter of aligning with the Los Angeles attitudes toward gender presentation. There was actually a legal element to this because at least at one of the venues she played, which was Joaquin's El Rancho, they had to get a special police permit for her to wear pants on stage. Her billings sometimes also came off as really odd as well, making her seem like a novelty act instead of an accomplished performer. One ad for her run at a venue called the Dollhouse on Ventura Boulevard touted, quote, the one and only Gladys Bentley. She's fat, tan and terrific. I would not want that as my billing. But whatever, her days of doing whatever she pleased in terms of her gender, expression and identity really did seem to be coming to a close, and her career was faltering.

[Tracy V. Wilson]

In August of 1952, an article written by Gladys appeared in Ebony magazine with the title I Am a woman Again. This is a fascinating and also troubling read, kind of a roller coaster of a narrative in which she shares the story of her early life and her problems with her family and her rise to fame. And then it describes what she calls the miracle that made her a woman, writing that it, quote, came about when I discovered and accepted the love and tenderness and true devotion of a man who loved me unselfishly and whose love I could return the awakening in me of the womanliness I tried to suppress.

[Holly Frey]

So Bentley's account describes a man who she names only as Don that she met through friends and found that she had feelings for. She described being confused and scared about these feelings and not knowing what to do with them, but also knowing that she wanted to marry him. And he was also very obviously interested in her. And she describes reading about how if you are feeling doubt about being with someone you truly love, that you have left God out of the union. This was in, like a religious book that she had. And she also says that all of this concern led her to visit a doctor. She went to that appointment wanting, she said, to talk about her weight. But when the doctor gave her a full examination, she described feeling relieved because that was what she actually wanted. And this doctor told her that she had a developmental issue with her sex organs. And he started her on a course of thrice weekly, quote, injection of female hormones. And that, she said, finally overcame the male hormones in her body. And then she said she felt free to get married to a man.

[Tracy V. Wilson]

This article has. There's a lot going on beyond that. After she describes this miracle, she starts the next paragraph by saying flatly that her marriage to Don did not last, but that she got married again, quote, today I am happily married, and I hope and pray this marriage will last. To J.T. gibson, well known west coast theatrical columnist. This is where it gets even wilder. The Ebony article must have actually come out to newsstands in July. A lot of publications put out their monthly issues. In this case the August issue. They actually dropped the month prior, because not only did J.T. gibson die in July of 1952, but one of his friends, photographer Maceo Sheffield, gave a statement to the press saying that Gibson was really angry about this article because it was not true. According to Sheffield, one of the last things Gibson said to him was, quote, I am not and have never been married to Gladys Bentley. I'm going to sue the Blank magazine for publishing a story stating that I am her husband in that confession article of hers. And then Gibson was found dead in a friend's car a few hours after this conversation. He had parked, and then he had an aneurysm rupture while he was getting out of the vehicle.

[Holly Frey]

So this denial of the marriage is also a mystery because Gibson was dead, and we cannot verify Sheffield's account. And that account is problematic for a couple of reasons. So, one, it first appeared in a Hollywood gossip column written by Harry Levette. Then it got kind of picked up and repeated in a lot of places, but that was the earliest mention I could find. And two, Maceo Sheffield was a very problematic figure. Um, it's sort of interesting that he's described as a photographer in every reference to him, because he was a disgraced LAPD detective who then transitioned into the film industry and became an actor. He also produced a few films, but photography never appears in his professional credits. He was actually charged with murder in 1927 when he raided a home on a tip of illicit alcohol, and he shot a young man named Samuel Faulkner there, which sparked protests in the city. Sheffield was tried for that murder but acquitted. Several LAPD cops who testified against him lost their jobs and soon after, Sheffield also left the force to pursue a film career. So we don't know if he just managed to somehow get out from under that, if people didn't realize that he was that detective that had been part of that scandal. So we don't know. Was Sheffield just trying to get his name in the paper with his claim about J.T. gibson's denial of a marriage to Gladys? The alternative there is that Gladys did lie in her story, which was printed in a very large publication. Or there's also the possibility that she and Gibson had some sort of understanding that Sheffield either didn't know about or that he was trying to posthumously distance his friend from Gladys for some reason. We are never gonna know, but just know that there's a whole lot of murkiness around this whole part of her story.

[Tracy V. Wilson]

In addition to all of the writing about her life, this multi page article also included a number of photos of Gladys. She wasn't in her tuxedo or dapper suits anymore, she's in a dress in every picture. And some of them she's shown with other well known musicians, including Louis Armstrong. The other photos though show her doing domestic chores typically associated with women. Each of them has a short caption about the activity that's being featured and then an additional piece of information. So one of them reads, quote, taste testing dinner she has prepared for husband J.T. gibson. Ms. Bentley enjoys domestic role which she shunned for years. She lives in modest, tastefully appointed home directly in rear of similar homes she purchased for her mother. In another photo, she's making the bed, and in yet another she's selecting jewelry. There are no pictures of either of the husbands that she mentioned in this piece.

[Holly Frey]

So this entire article seems like such a departure from the life Gladys Bentley lived in the years prior that it seems confusing and almost shocking. But this is also an instance where context really, really matters. This article came out in the middle of the Lavender scare when homosexuality was not just seen as deviant, it was criminalized. In 1947, five years before Bentley shared this story in Ebony, the U.S. park Police, which is part of the National Park Service, had instituted a sex perversion elimination program. And there was also legislation introduced in Congress that labeled homosexuals as sexual psychopaths. Most of these laws targeted gay men. But somebody like Gladys, who was a very well known and very out lesbian performer, wasn't going to fly under the radar in a country that was gripped by this misguided notion that same sex attraction was criminal and dangerous. Most modern queer scholars and historians, when Looking at this article and thinking about all of its nuance, see it as an effort on Gladys Bentley's part to straight wash her reputation to try to save her music career.

[Tracy V. Wilson]

Yeah, this was really. I mean, we've talked about like laws about obscenity and earlier laws about things like cross dressing. But this was a time when more queer people were becoming more visible and there was a big backlash against that. So, like, as a movement for equal rights was growing and developing, like there was just an onslaught of laws and social mores and all of that that she would have been targeted by.

[Holly Frey]

Yeah. And a lot of people willing to stoke fear of anyone who was not heteronormative.

[Tracy V. Wilson]

Yeah. In September of 1952, Gladys got married again. And this time there were pictures. Her new husband was Charles Robert, a 28 year old cook from Sacramento. Gladys was 45 at the time. Newspaper reports said that they had been dating for only five months. And if that's the case, that means that they were seeing each other while she claimed that she was married to her second husband. But also we just don't have a lot of information about Charles or about their life together. And so that that has led to some speculation that it too might have been for show.

[Holly Frey]

In the 1950s, Gladys wrote a book about her life titled if this Be Sin. But it was never published and there doesn't appear to be a surviving manuscript in that article. There is also a photograph of her typing on a typewriter, allegedly working on this book. She mentioned the book in that same you Bet yout Life appearance that we mentioned at the top of the show. And Bentley also played piano on that program as she sang them Their Eyes. And you can find this video online. It is so clear why she was a beloved performer. This is, to the best of my knowledge, the only actual footage that we have of her performing. Her presence and her energy, just incredibly compelling. Her vocal style and the way she phrased the verses with her breath was really unique. She would sing lines in this sort of staccato style. With each word given its own very brief, punchy moment. It is 100% easy to see why people would have flocked to her shows.

[Tracy V. Wilson]

At the beginning of February 1960, Gladys got a cold and that quickly got worse. She developed pneumonia and she died at home on February 8. She was only 52. Her obituary mentions that she lived with her mother. No husband was mentioned as next of kin, so we don't really know what happened. Regarding her third marriage, when her mother Mary died six years later, she was buried Next to Gladys.

[Holly Frey]

I love Gladys.

[Tracy V. Wilson]

Yeah.

[Holly Frey]

I have so much to talk about on Friday.

[Tracy V. Wilson]

Yeah.

[Holly Frey]

But right now I have listener mail that's not about anything this serious at all. But I love it so much it's not even really about history.

[Tracy V. Wilson]

Okay.

[Holly Frey]

It's about Bluey.

[Tracy V. Wilson]

Yeah, I know this email. I read it this morning and was delighted. I'm excited for people to hear it now.

[Holly Frey]

I love it. It also validates some feelings I've had about Bluey and real estate for a while. This is from our listener Ian, who writes. Hi ladies. In a recent behind the scenes episode, one of you mentioned you like watching Bluey as escapism. Listen, I watched it this morning while I had coffee. This letter continues. So I thought you might find this new story from 2020 interesting. A real estate agent who must have watched too many Bluey episodes no such things with their kids realized that the Bluey or Heeler family home is a Queenslander style house. It has at least 15 rooms, has a massive backyard with a full size tree in it and is in a major suburb of Brisbane. They calculated the Heeler family home would be worth at least $4 million Australian. That's about US 2.8 million. Listen, that was six years ago. I bet it's worth a lot more now. Queenslander style of home was developed in tropical Queensland, Australia in the age before air conditioning. They're made out of wood. They have wraparound verandas to keep sun out and improve cooling and they are elevated off the ground to provide extra cooling and avoid flooding. For a while you could have stayed in the real Bluey house. A real Queenslander home was decorated as the Heeler family home and was available on Airbnb. But I think that home has now become a regular family home. That lucky family. Whilst we were at it, Peppa Pig is another TV show which has been popular in Australia. There was however, one episode which was not played on Australian tv. In it, Peppa told her friends that spiders cannot hurt you. This episode was not banned. It is just that abc, the Australian Broadcasting Corporation, decided it was not a good idea to show this episode in a country where spiders can actually hurt you. As for pet tax, I have attached a couple of pictures of our cat Trim and our dog Ringo. Ringo sadly died of old age over a year ago. In one picture you have Trim cuddling up to Ringo. The other picture you have Ringo next to a statue of the original Trim who was Matthew Flinders cat and was the first cat to circumnavigate Australia. Thanks for keeping me going. At the gym. Ian. Okay. I love everything about this email.

[Tracy V. Wilson]

Yeah.

[Holly Frey]

I also love this cat and dog. They are the cutest things on the planet. Yeah, that dog. I just know that dog got kissed on the snoot 27 times a day minimum. Well deserved.

[Tracy V. Wilson]

I think Peppa Pig is a. A British show. I don't know. Is it? But like, but I don't know for. But like, there are also spiders that can hurt you in North America.

[Holly Frey]

Yeah. Peppa Pig's huge here and I don't

[Tracy V. Wilson]

think I would say there are more spiders that can hurt you worse in Australia.

[Holly Frey]

Yeah, I mean, but most house spiders are.

[Tracy V. Wilson]

Most spiders you're going to see are fine.

[Holly Frey]

Listen, I live with a, in North America, significant level arachnophobe. So I understand the fear of spiders.

[Tracy V. Wilson]

Even though.

[Holly Frey]

Though, yeah, I love them. It's my job to corral them and escort them outside.

[Tracy V. Wilson]

I do not dislike them, but I do know what black widows and brown recluses look like and those are the kinds that live in places I have lived.

[Holly Frey]

Yeah, you are right. Peppa Pig is British, by the way. You could tell that that's a show I've never glommed onto.

[Tracy V. Wilson]

And I have no idea what the venomous spider situation is in Britain.

[Holly Frey]

It isn't. I think that's what's up to the best of my knowledge, I don't think they have any dangerous ones, but I could be wrong. Correct me if I'm wrong. Anybody. If you wanna correct me, you can do that in an email.

[Tracy V. Wilson]

If British listeners want to write in about whether there are venomous spiders.

[Holly Frey]

Yeah. I feel like I have heard a factoid that they don't have them, but I may have a false memory. If you wanna correct us, you can do [e-mail] if you want to look up our show notes to see any of the articles, papers, et cetera that got used for this episode and any other, you can find [e-mail] we also would love it if you would subscribe to the show. You can do that on the iHeartRadio app or anywhere you listen to your favorite podcasts.

[Tracy V. Wilson]

Stuff youf Missed in History Class is a production of iHeartRadio. For more podcasts from iHeartRadio, visit the iHeartRadio app, Apple Podcasts or wherever you listen to your favorite shows, experience scenic views and private rooms that let you stretch out, enjoy hassle free travel as it should be on Amtrak. Book some Z's at Amtrak.com, amtrak Retrain Travel brought to you in part by Vital Farms. I love eggs. I turn to them all the time as a quick and easy way to start a meal. And Vital Farms eggs are brought to you by hens that have access to fresh air and sunshine and you can actually look up on the carton and see the farm that those eggs came from. Vital Farms is also a certified bee corporation with a purpose to improve the lives of people, animals and the planet through food. Look for the black egg carton in the egg aisle and visit vitalfarms.com to learn more. Vit Good eggs no shortcuts Wouldn't it

[Holly Frey]

be great to never buy gas again? EVs are as easy to charge as your phone and they are a perfect addition to your everyday life. Most people are only driving about 40 miles a day, and most EVs can handle 200 to 400 miles of range on a charge. And there are hundreds of EV models available today, so there's something perfect for every lifestyle and budget. I drive an ev. I've had it for a couple of years. It's my favorite car I've ever owned. It is so fun to drive. The pickup is incredible. It's super agile and it is easy to maintain. The way forward is electric. Learn more at electricforall.org @BritBox Character is

[BritBox Announcer]

Everything Stream the iconic characters defining British TV on BritBox, including Ludwig.

[Tracy V. Wilson]

I think I might just have solved a murder.

[BritBox Announcer]

Vera.

[Holly Frey]

Now we're getting somewhere.

[BritBox Announcer]

Agatha Christie's Poirot, I'm sure and more beloved favorites I'm a Policeman.

[Holly Frey]

Unprofessional.

[T-Mobile Advertiser 1]

I'm a Time Lord named the Duchess of York.

[BritBox Announcer]

Once you know them, you never quite forget them.

[T-Mobile Advertiser 1]

I ain't being vain, I just am special.

[BritBox Announcer]

Stream the best of British TV on BritBox. Watch with a free trial today at britbox. Com.

[Tracy V. Wilson]

This is an iHeart podcast. Guaranteed Human.