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60. Eric Massa
Initially came under scrutiny when reports surfaced that he had harassed a male staffer. Quickly spiraled out of control into stories of an inappropriate tickle party; a nude... READ MORE
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59. Tyler Perry
Brother’s entire shtick is ripped off from Carol Burnett and Mama’s Family . Enough already. LOOKS LIKE Um, a black dude in... READ MORE
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58. Frank Black
REASON HE’S ON THE LIST The secret to the Pixies frontman’s Shrek-like physique? Eat a lot, Doolittle . That, and workout tips from Robert Smith. We loved the... READ MORE
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57. Jayson Williams
Even canine-hating quarterback Michael Vick looks like an amateur compared to this crazy-eyed former NBA star. Williams — who has a history of brawls and weapon-brandishing — is finally... READ MORE
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55. Tom Sizemore
Sizemore pissed away movie-star looks and a promising acting résumé ( Heat , Saving Private Ryan , Black Hawk Down ) for a life in the meth... READ MORE
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54. Tareq Salahi
One day you’re bragging on Facebook about how you infiltrated a White House dinner without an invitation. The next you’re being questioned by federal investigators for cracking their security... READ MORE
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53. Jon Gosselin
Following his divorce from fellow reality-TV leech Kate, Gosselin left his brood of eight children to launch a mid-life crisis for the record books. His dating pool has included... READ MORE
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52. Tucker Max
Picketed by campus feminists who paint him as the patron saint of date-raping frat boys, and voted the second-biggest “Douche of the Decade” by the readers of Gawker, this... READ MORE
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51. Bill Clinton
Bill Clinton’s penis famously wrecked the first Clinton presidency; in 2008 it may have wrecked Hillary’s before she could even get elected. According to the tell-all chronicle Game... READ MORE
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