2019 Icons

  1. Ethel Allen
  2. Kwame Anthony Appiah
  3. Gladys Bentley
  4. Jackie Biskupski
  5. Kate Bornstein
  6. Ana Brnabić
  7. Pete Buttigieg
  8. Eliza Byard
  9. Brandi Carlile
  10. George Chauncey
  11. Lou Chibbaro Jr.
  12. Sharice Davids
  13. Babe Didrickson
  14. Cheryl Dunye
  15. Lillian Faderman
  16. Ronan Farrow
  17. Jewelle Gomez
  18. Emma González
  19. Sherenté Harris
  20. Rock Hudson
  21. Robert Indiana
  22. James Ivory
  23. Anne Lister
  24. Arthur Mitchell
  25. Julia Morgan
  26. Anaraa Nyamdorj
  27. Jared Polis
  28. Angela Ponce
  29. Keshav Suri
  30. Lillian Wald
  31. Edith Wharton

Gladys Bentley

Blues Performer

b. August 12, 1907
d. January 18, 1960

“It seems I was born different. At least, I always thought I was.”

Gladys Bentley was a celebrated African-American blues singer and pianist. Her cross-dressing lesbian persona, deep voice and bawdy lyrics catapulted her to fame during the Harlem Renaissance.

Born in Philadelphia, the eldest child of an African-American father and a Trinidadian mother, Bentley grew up poor. She felt scorned, particularly by her mother, who wanted a son. Bentley believed the rejection helped shape the gender nonconformity she exhibited from an early age.

In school Bentley faced ridicule for wearing boys’ clothes and for her crushes on female teachers. Doctors eventually diagnosed her with “extreme social maladjustment.” At age 16, no longer able to endure the abuse she received from her family and peers, she moved to New York City’s Harlem neighborhood.

The 1920s welcomed an explosion of African-American arts and culture in Harlem, and Bentley flourished there. Wearing men’s formal attire, which became her trademark, she quickly found success performing at local speakeasies and blues clubs. She recorded with a variety of music labels and signed for a year with OKeh Records.

Bentley adopted the stage name Bobbie Minton and headlined at Harry Hansberry’s Clam House, a popular nightspot frequented by gays and lesbians. She later headlined at the Ubangi Club, backed by a chorus of drag queens. Bentley sang unabashedly about sexuality and male abuse of power. She quickly became one of the most famous entertainers—and famous lesbians—in Harlem. After earning acclaim in New York, she toured nationwide, performing in Chicago, Hollywood and other major cities.

Though interracial and same-sex marriage were illegal, Bentley married a white woman in 1931 in a public civil ceremony in Atlantic City, New Jersey. As the decade pressed on and the Great Depression shrouded the nation, social mores began to shift. Prohibition ended, and Bentley tried unsuccessfully to bring her act to Broadway. Her performances were often shut down by police. In 1937 she moved to Los Angeles, where her success continued, but some club owners forced her to wear dresses.

In the 1950s, McCarthyism all but extinguished tolerance in America, and Bentley tried to transform her image. In a 1953 Jet magazine article, she announced that she had transitioned from the “third sex” to a “true female.” She dressed like a woman and claimed to have married a man, Charles Roberts, a Los Angeles cook.

Bentley died of pneumonia at her Los Angeles home. Almost 60 years later, The New York Times published her obituary as part of its “Overlooked” series.