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Born into a working class family in San Diego on November 17, 1960, RuPaul Andre Charles had an early fascination with things feminine. By the age of four, he was already an effeminate boy, imitating Diana Ross and Jane Fonda and beginning to be labeled a sissy. His parents divorced when he was seven, and RuPaul was raised from then on in a household of strong women, consisting of his adored twin sisters, seven years older than himself , and his mother, whom he describes in his autobiography as "the fiercest drag queen I've ever known." RuPaul was ready to come out as a gay man by the time he was fifteen, and he moved into his sister's house, then moved with her to Atlanta. There, free from parental constraints, he threw himself into the gay life, performing in drag clubs, and, briefly, with his own band, RuPaul and the U-Hauls.


 In 1987, relocating to New York, RuPaul landed roles in such films such as Spike Lee's Crooklyn in 1993, Betty Thomas's 1995 The Brady Bunch Movie, Barry Shils' 1995 masterpiece Wigstock: The Movie, Wayne Wang's Blue In The Face also in 1995, Beeban Kidron's To Wong Foo, Thanks For Everything, Julie Newmar in 1996, Jamie Babbit's But I'm a Cheerleader in 2000, in which he plays the part of an ex-gay camp counselor in "male drag", and in 2008 alongside fellow drag performer "Lady Bunny" in Todd Stephens' Gays Gone Wild, the sequel to the 2006 cult hit Another Gay Movie.

In the early 1990s, RuPaul worked the Georgia club scene and was known as by his full birth name. He appeared for many years at the annual Wigstock drag festival and contributed an appearance to the documentary Wigstock: The Movie. In the '90s, RuPaul was known in the UK for his appearances on the Channel 4 series Manhattan Cable, a weekly series produced by World of Wonder and presented by American Laurie Pike about New York's wild and wacky Public-access television system.

n 1993 RuPaul recorded dance/house albums which included Supermodel of the World. They were released through the hardcore rap label Tommy Boy, spawning the dance track hit "Supermodel (You Better Work)", which was a hit song for Rupaul. The music video was an unexpected success on MTV channels, as grunge-rock (Nirvana) and gangsta rap were popular at the time. The song peaked at #45 on the Billboard Hot 100. It further charted on the UK Singles Chart, peaking on the top 40 at #39. The song found the most success peaking at number 2 on the US dance music charts (known as the Billboard Hot Dance Music/Club Play chart). Airplay, heavy rotation of the music video on the MTV network and television appearances on popular programs like The Arsenio Hall Show popularized the song. His next two songs/videos, "Back to My Roots" and "A Shade Shady (Now Prance)" both went #1 on the Billboard Hot Dance Music/Club Play charts and further developed his campy persona. Between them, House of Love was released without a video. It failed to place on any US charts, despite rising to #68 on the UK Singles Chart.

In mid 2008, RuPaul began producing RuPaul's Drag Race, a reality television game show which aired on Logo in February 2009. On the show, top drag queens compete to be selected by RuPaul and a panel of judges as the number one drag performer in the country. The winner of Season 1 was Bebe Zahara Benet. One of the contestants, Nina Flowers, was chosen by fans as "Miss Congeniality" through voting on RuPaulsDragRace.com.

In publicity preparation for the new show, RuPaul made appearances as a guest on several other shows in 2008 including as a guest judge on Project Runway and as a guest "chef" on Paula's Party.

The concept of drag is all about manipulating surface images, and RuPaul's life has given him an intimate understanding of the ways in which the surface can be deceptive.