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40. Bruce Jenner

Poor Bruce Jenner. In 1976, he single-handedly wrested the decathlon gold medal from those godless Soviets in the Olympics. He was even on a Wheaties box. But then he headed into a 20-year-long midlife crisis. He underwent a botched face lift; he spawned Brody Jenner of The Hills in his second marriage. And then, worst of all, he married Kris Kardashian in 1991. Seeing just how emasculated he has become every week on TV is truly heart-wrenching. Somebody save him — or at least give him a hug.
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