The 13 Greatest Sissies of All Time

Whoa, nellies!

It’s never been easy being a sissy. Society has long vilified any behavior in men that even hints of effeminacy—acting like a woman meant that you were weak, that there was something wrong with you.

That you were gay.

Sissies have even faced rejection from their fellow gays: How many times you’ve seen “no fems” or “masc only” on a hookup profile? But the truth is it takes courage to be a sissy—to revel in thumbing your nose at society’s expectations of masculinity.

In celebration of nancy boys everywhere, we’re profiling 13 legendary sissies who made it safe to be swishy in the face of rejection, ridicule and even violence.

  1. Oscar Wilde

    LEHTIKUVA / EVERETT COLLECTION / Jerry Tavin

    The author of The Importance of Being Earnest and The Picture of Dorian Grey, Wilde was imprisoned for the crime of homosexuality and died penniless in exile.

    But even in his  final days, he kept his sissy wits about him, reportedly remarking, “My wallpaper and I are fighting a duel to the death. One of us has to go.”

  2. Quentin Crisp

    Michael Ward/Getty Images

    Born eight years after Wilde’s death, Crisp took up his fallen sissy mantle and skipped all the way through the 20th century, becoming the grand dame of swishes.

    Embracing his feminine tendencies at an early age, Crisp traipsed about pre-WWII London in makeup and blouses, receiving vicious beatings for breaking social norms. He eventually parlayed his eccentricities into a bona fide career — if you consider “raconteur” a career. Which I do.

    His autobiography, The Naked Civil Servant, is essential reading on the art of life.

  3. James Baldwin

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    The prolific novelist, essayist and playwright began exploring and challenging ideas of race with the novel Go Tell It on the Mountain and his collection of essays Notes of a Native Son. But for his third effort, Baldwin pulled a literary about-face and produced probably the greatest gay-themed novel ever, Giovanni’s Room.

    When he wasn’t actively participating in the civil rights movement, Baldwin also BFF’d and inspired a trio of epic ladies: Maya Angelou, Nina Simone and Toni Morrison. Oh, the soulful, life-affirming kikis they must have had.

  4. Liberace

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    When you think subtlety, one name comes to mind: Liberace. Behind that candelabra, a sequined-tuxedoed Lee tickled the ivories in Vegas — mostly for straight older ladies who were willfully oblivious to his, shall we say, particular charms.

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    But it was a different time and a man with more white diamonds than Liz Taylor would barely raise eyebrows and could become the highest paid entertainer in the world just for playing a piano with remarkable flair.

  5. Little Richard

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    Taking a note from the Liberace playbook, Little Richard cemented his reputation as the “architect of rock and roll” with his groundbreaking hits in the ‘50s, including “Tutti Frutti,” “Good Golly Miss Molly” and “Long Tall Sally.”

    Always cagey about his sexuality, Little Richard’s androgynous look was born — at least in part — out of practicality. “I wore the make-up so that white men wouldn’t think I was after the white girls,” he told a reporter in 1984. “It made things easier for me, plus it was colorful too.”

  6. Truman Capote

    William E. Sauro/New York Times Co./Getty Images

    Capote heralded his arrival with an eerily seductive jacket photo on his first novel, Other Voices, Other Rooms. He continued on to early success with In Cold Blood and Breakfast at Tiffany’s before settling into a comfortable life as official hanger-on to New York society ladies like Lee Radziwell and Babe Paley.

    During his long, boozy decline, Capote struck a gin-soaked match and burned nearly every bridge to the ground. A series of short stories ridiculing his gal pals and their husbands through thinly-veiled characterizations formed the basis of his unfinished novel, Answered Prayers. The original Burn Book, Answered Prayers was published posthumously in 1986.

  7. Boy George

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    Who would really want to hurt Boy George? In his Culture Club heyday, this colorful imp was America’s sweetheart with his non-threatening androgyny and bag full of pop hits. He famously professed his preference for a “nice cup of tea” over sex, even though he was in a rocky relationship with CC drummer Jon Moss at the time.

    George’s life and times would later become the basis for the short-lived Broadway musical, Taboo, for which he wrote the lyrics and snatched a Tony nomination.

  8. Johnny Weir

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    For decades male figure skaters fought against the notion that they were swish. Weir, meanwhile, embraced it, with fierce costumes—both on and off the ice— and Gaga-channeling short programs. Challenging the sport’s conventions, Weir was a polarizing figure in skating until his retirement in 2013.

    Even with his blades hung up with care, Weir continues to turn heads with his unique sports commentary with new straight-girl BFF Tara Lipinski.

  9. Paul Lynde

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    Paul Lynde hammed his way through Bewitched as that mischievous but lovable warlock, Uncle Arthur. And if he and Endora (played by noted lesbian Agnes Moorehead) went at it, watch out.

    Lynde cemented his place in entertainment history as Hollywood Squares’ sassy center square and Templeton the Rat in Charlotte’s Web, but made countless sitcom appearances and was in the original Broadway cast of Bye Bye Birdie. All while his sexuality was Hollywood’s worst-kept open secret.

  10. Lindy from “Car Wash”

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    What could easily have been offensive became one of the highlights of this 1976 blaxploitation classic, as Antonio Fargas owns everything as Lindy, one of the first black queer characters in film.

    Being a trailblazer, Lindy also helped introduce the word to reading when he shot down a homophobic hater.

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    YAS, MAMA!

  11. Blaine Edwards and Antoine Merriweather from “In Living Color”

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    In Living Color’s pearl-snatching answer to Siskel and Ebert, Blaine and Antoine (Damon Wayans and David Alan Grier) shared their sharp observations on the best and worst cinema had to offer, before branching out into other areas in need of their particular brand of critiques.

    Some cringed at two straight men miming gay stereotypes, but the performances were so over-the-top they almost transcended parody. Twenty years later, Blaine and Antoine’s looks are still giving life.

    Two snaps around the world and back!

  12. Jack McFarland from “Will & Grace”

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    Sean Hayes’ Jack McFarland was the flamboyant foil to Will’s “straight man,” embracing—and at times lampooning—stereotypes of the quixotic Manhattan gay.

    And with Megan Mullalley’s gin-soaked Karen Walker, this spastic ball of energy also formed one half of the greatest comedic duo in recent sitcom history. As soon as Jack and Karen bumped tummies, it became clear: this was their world and Will and Grace were simply living in it.

  13. Kurt Hummel from “Glee”

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    Before Klaine overshadowed everything, Kurt (Chris Colfer) was a sweet kid with a sweet voice and an even sweeter face.

    “Porcelain,” as Coach Sue (not-so-affectionately) referred to him, became a hero to a new generation of effeminate kids, who just wanted to sing their little hearts out—and maybe wear a Ralph Lauren poncho without fear of repercussion.

Lester Fabian Brathwaite is an LA-based writer, editor, bon vivant, and all-around sassbag. He's formerly Senior Editor of Out Magazine and is currently hungry. Insta: @lefabrat