The Gender Benders

• Name: Flip Wilson
  Profession: Actor/Comedian
  Gender Bender: As the strong-looking, colorfully-dressed, flirtatious and outspoken Geraldine Jones, Wilson is credited with negotiating race and class bias by positively characterizing the average, working class black female.
  Claim to Fame: After being featured on shows such as 'Laugh-In,' 'The Ed Sullivan Show' and 'The Tonight Show,' he landed his very own sketch variety show, which debuted on NBC in 1970.
  Factoid: Flip Wilson was born Clerow Wilson, Jr. in Jersey City, NJ on December 8, 1933. On November 25, 1998 he succumbed to complications of liver cancer.
  
  
  
  

  Everett Collection

• Name: Milton Berle
  Profession: Actor/Comedian
  Gender Bender: During his television heyday, "Uncle Miltie" (as many referred to him as) donned wigs and dresses during his slapstick comedy antics.
  Claim to Fame: In 1948, NBC brought 'Texaco Star Theater' from radio to television, later naming Berle as the permanent host. The vaudevillian-styled show became a ratings hit, winning Emmy Awards after its first season.
  Factoid: Milton Berle was born Mendel Berlinger in New York City on July 12, 1908. He passed away at the age of 93 on March 27, 2002.
  
  
  
  

  AP

• Name: RuPaul
  Profession: Singer/Actor/Drag Performer/Former Talk Show Host
  Gender Bender: RuPaul, born RuPaul Andre Charles, became not only the first drag queen supermodel after signing a contract with M.A.C. cosmetics but he was also the first drag queen to have his own talk show.
  Claim to Fame: At the height of the supermodel era, RuPaul released a dance/house album called 'Supermodel of the World' lead by the hit single 'Supermodel (You Better Work).' It became an MTV hit and topped the dance charts.
  Factoid: On his 'Foxy Lady' album, he covered Diana Ross's 'Work That Body' and also appeared on her music video for the single, 'I Will Survive.'
  
  
  
  

  Retna

• Name: Wesley Snipes
  Profession: Actor
  Gender Bender: Snipes's character, "Noxeema Jackson," in 'To Wong Foo Thanks for Everything, Julie Newmar' is a drag queen who, along with fellow drag queens Vida Boheme and Chi-Chi, sets off on a road trip to Los Angeles only to have their car break down along the way.
  Claim to Fame: Though his first movie was 'Wildcats' with Goldie Hawn, Snipes, made a name for himself in two popular black films of the early 90s, playing Nino Brown in 'New Jack City' and as Shadow Henderson in Spike Lee's 'Mo' Betta Blues.'
  Factoid: Snipes holds a fifth degree black belt and also practices Capoeira, a Brazilian martial arts.
  
  
  
  

  Everett Collection

• Name: Boy George
  Profession: Singer/Songwriter
  Gender Bender: Influenced by David Bowie and Iggy Pop, Boy George's androgynous look made him a stand-out in his group Culture Club.
  Claim to Fame: Culture Club's 1983 debut, 'Kissing To Be Clever,' included the #1 song 'Do You Really Want To Hurt Me.'
  Factoid: Boy George, real name: George Alan O'Dowd, later confessed to being bisexual and dating his Culture Club drummer Jon Moss for whom he wrote a great deal of his hit songs for.
  
  
  
  

  Getty Images

• Name: Sylvester
  Profession: Musician/Drag Performer
  Gender Bender: Sylvester got his start performing with a group of transvestites called The Cockettes in San Francisco. Record label pressure to reshape his image resulted in his reportedly showing up to meetings in full-on drag.
  Claim to Fame: His first solo album, 'Step II,' which was released in 1978, earned him the name "The Queen of Disco" following the success of two disco classics, 'You Make Me Feel (Mighty Real),' and 'Dance (Disco Heat).'
  Factoid: Before he passed away from complications due to AIDS, Sylvester (real name: Sylvester James) lived out one of his dreams, singing back-up for his idol Aretha Franklin on her album 'Who's Zoomin' Who?'
  
  
  
  

  Jeff Katz

• Name: Felicity Huffman
  Profession: Actress
  Gender Bender: As "Bree" in 'Transamerica,' Huffman plays a man-to-woman pre-operative transsexual who finds out that she has a son before her final surgical operation.
  Claim to Fame: Huffman has gained popularity as the character Lynette Scavo on ABC's 'Desperate Housewives.'
  Factoid: In 2005, Oprah Winfrey granted Felicity's "Wildest Dream" when she got to sing backup for her idol Tina Turner on Winfrey's talk show.
  
  
  
  

  The Weinstein Co.

• Name: Grace Jones
  Profession: Model/Actress/Singer
  Gender Bender: On the cover of her 1981 album, 'Nightclubbing,' Jones flaunted an androgynous look, with square-cut hair and a padded suit jacket, cigarette in mouth. Her height and overall new look was said to have influenced the cross-dressing movement of the 1980s.
  Claim to Fame: Jones began her career as a model in New York and was once a muse to Andy Warhol. Her disco recordings were welcomed by a loyal gay following. Jones also appeared in 'Boomerang' as Helen Strangé.
  Factoid: Jones was born in Spanish Town, Jamaica.
  
  
  
  

  Wire Image

• Name: Dustin Hoffman
  Profession: Actor
  Gender Bender: In 'Tootsie,' Hoffman played Michael Dorsey, an unemployed actor, who takes on the role of "Dorothy Michaels" a female soap opera actress and later falls in love with the show's leading actress.
  Claim to Fame: Dustin Hoffman's first memorable role was in the 1967 film 'The Graduate' as a young college grad named Benjamin Braddock who gets himself into a messy situation by having an affair with a married woman and falling in love with her teenage daughter.
  Factoid: In 1982, he reportedly wanted to play the title role in 'Gandhi,' but ended up signing up for 'Tootsie.' Oddly enough, he lost the Oscar for 'Tootsie' to Ben Kingsley who played Gandhi.
  
  
  
  

  Getty Images

• Name: Chiwetel Ejiofor
  Profession: Actor
  Gender Bender: In the hit British comedy 'Kinky Boots,' Charles Price takes a last stab at saving his family's men's shoe business when he listens to a suggestion from Lola, a flamboyant drag queen and cabaret singer played by Ejiofor. Lola suggests that he make high heel shoes for drag queens.
  Claim to Fame: Ejiofor, a noted London theatre actor, won a British Independent Film Award for his first leading film role in 2002's 'Dirty Pretty Things.' In 2008, he won the prestigious Laurence Olivier "Best Actor" Award for his role as 'Othello.'
  Factoid: In 2006, Ejiofor and actor Clive Owen starred in two movies back-to-back, 'Inside Man' and 'Children of Men.'
  
  
  
  

  Everett Collection