RuPaul Born in San Diego, California, RuPaul's tumultuous youth was marked by the bitter divorce of his parents. RuPaul struggled as a musician and filmmaker in Atlanta in the 1980s. In Atlanta, he participated in underground cinema, helping create a low-budget picture known as "Starbooty" (and an album by the same name). RuPaul came into the public eye in 1989, appearing in the music video for The B-52's immensely popular single "Love Shack". In the early 1990s, RuPaul became a fixture in the New York club scene, and was voted "Queen of Manhattan" by area club owners, promoters and DJs. RuPaul was often seen pushing around a shopping cart outside of dance clubs to distribute flyers for upcoming events. It was during this time that RuPaul penis i love began performing under the name RuPaul Charles and later simply RuPaul. Initially participating in "genderfuck"-style performances, RuPaul performed solo and in collaboration with other bands at several New York nightclubs, most notably the Pyramid Club. RuPaul also appeared for many years at the annual Wigstock drag festival, and appears in the documentary "Wigstock: The Movie", later returning to the Wigstock stage in 2004. In 1994, RuPaul recorded a renewed version of Elton John's 1970s hit single "Don't Go Breaking My Heart" for John's Duets album, and filmed a video for the track with John.
In 1995 RuPaul was signed to a modeling contract for MAC cosmetics, making him the first transvestite supermodel. He began releasing pop albums starting with Supermodel of the World in 1993, which spawned the #1 dance hit "Supermodel (You Better Work)". In 1996, he landed a talk show on VH1, appropriately called The RuPaul Show, where he interviewed celebrity guests and musical acts. Because of his strong fan base within the gay community, RuPaul has performed at gay pride events and numerous gay venues. In 1997, he released a Christmas album entitled Ho, Ho, Ho and has had guest appearances in many films including both Brady Bunch movies, in which he played Jan's female guidance counselor.
RuPaul caused a bit of controversy at the MTV Music Awards when he was given the opportunity to present an award with legendary actor Milton Berle, who performed an altogether different type of drag early in his career. The two had conflicts back-stage, and when Berle inappropriately touched RuPaul's breasts, RuPaul ad-libbed the line "So you used to wear gowns, but now you're wearing diapers." The press picked this up as a crack in the "love everyone" message RuPaul presented, and depicted the incident as a young newcomer treating a legend poorly. Eventually the hullabaloo faded.
It was also in 1996 that RuPaul helped launch the return of WKTU radio in New York City. RuPaul would serve as host of the morning show on WKTU until 1998.
RuPaul was nominated for an Emmy award for his role (as a man) alongside Linda Hamilton in the made-for-TV Movie A Mother's Prayer. In the late 1990s he released his autobiography, Lettin' It All Hang Out. In 1997, he teamed with Martha Wash to remake the classic disco anthem, "It's Raining Men".
In 2004 RuPaul released his third album, Red Hot. It received some dance radio and club play, but very little press coverage. On his blog, RuPaul discussed how he felt betrayed by the entertainment industry, particularly the gay press. In one incident he noted that the magazine Entertainment Weekly refused to review the album, but instead asked him to make a comedic contribution to a fashion review article. He likened the experience to "a black person being invited to a party but only if they'll serve."