Ellen DeGeneres & Anne Heche

Winner: Ellen DeGeneres Stand-up comedian Ellen DeGeneres and actress Anne Heche announced their relationship in 1997, the same year Ellen came out on "The Oprah Winfrey Show" and then during her own sitcom, "Ellen." When the pair split in 2000, they went very different ways: DeGeneres parlayed an Emmy-hosting gig into growing stardom, including a popular talk show and, most recently, replacing Paula Abdul as a judge on "American Idol." Heche, just after the breakup, underwent a very public breakdown, at one point declaring herself an extraterrestrial deity. While Heche recovered and won back some fans on the series "Men in Trees," DeGeneres is the clear winner.
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