2020 Icons

  1. Nikolay Alexeyev
  2. Deborah Batts
  3. Angie Craig
  4. Emily Dickinson
  5. Felicia Elizondo
  6. Rob Epstein
  7. Emile Griffith
  8. Menaka Guruswamy & Arundhati Katju
  9. Alexander von Humboldt
  10. Christopher Isherwood
  11. Moisés Kaufman
  12. Lori Lightfoot
  13. Claudia López
  14. Bernárd Lynch
  15. Anne McClain
  16. Kate McKinnon
  17. Harris Glenn Milstead “Divine”
  18. David Mixner
  19. Lauren Morelli
  20. Ifti Nasim
  21. Jess O’Connell
  22. Mary Oliver
  23. Billy Porter
  24. Laura Ricketts
  25. Angelica Ross
  26. Sappho
  27. Megan Smith
  28. Baron von Steuben
  29. Laxmi Narayan Tripathi
  30. Deborah Waxman
  31. Lil Nas X

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.