Diana Ross
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Madonna may be the modern mistress of self-reinvention, but Diana Ross did it first. The Detroit-born singer started with a bouffant in the early '60s as one-third of The Supremes, harmonizing on girl group hits like "You Can't Hurry Love." In the '70s, despite resembling an even more waifish Michael Jackson in drag, Ross played jazz singer Billie Holiday in Lady Sings the Blues and nabbed an Oscar nomination for Best Actress. In the '80s, Ross' hair became the big, bouncy 'fro we all know and love now, while her music career centered on her hit remake of "Why Do Fools Fall in Love" and elbowing former fellow Supreme Mary Wilson out of the spotlight at the Motown Records 25th anniversary special. The '90s saw Ross perform the halftime show at Super Bowl XXX and return to acting with the film Double Platinum (co-starring R&B singer Brandy), while the new millennium found her booking a Supremes reunion tour that died of a case of severely low ticket sales after nine dates, and getting pulled over for drunken driving in Tucson. Her 2007 album, I Love You, peaked at number 32 on the pop charts, and while nobody can predict what Ross will do next, one thing is for certain: She will continue to inspire drag queens almost as much as Cher does.
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