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You may know RuPaul as perhaps the world's most famous drag queen, but she's won a few more hats (and wigs) over the course of her career. Born RuPaul Andre Charles, he got his start as a musician, dancer, actor and underground filmmaker in Atlanta. He also started doing drag, making a name for himself (going by only his first name) as a beautiful, blonde, 6'7" (plus heels!) queen in the south and, later, New York, where Rupaul became a regular fixture at the annual Wigstock festival. Then in 1993, she released her debut album on Tommy Boy. Surprising industry insiders, the album was a hit, spawning the Billboard-charting single "Supermodel (You Better Work)" and turning RuPaul into a household name. She parlayed that fame into a remake of "Don't Go Breaking My Heart" with Elton John, a MAC modeling contract, an autobiography and a long-running VH1 talk show. None of the six albums that followed (including a rerelease of the soundtrack to Starrbooty, an underground film from Ru's Atlanta days) did as well as her debut. But in 2009, the diva ascended into the pop cultural pantheon again with the hit show RuPaul's Drag Race, a Top Model-style reality contest for drag performers.