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  • 60. Eric Massa

    Spongebob Grabpants

    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

    Stepin Wretched

    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

    Black Frankfurter

    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

    Fresh Prince of Bel Err

    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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  • 56. Owl City

    Kidz Bop

    Owl City’s insufferable, inescapable Top 40 crossover hit “Fireflies” sounds like someone has kidnapped Death Cab’s Ben Gibbard, cut off his testicles, and is holding him for ransom in... READ MORE

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  • 55. Tom Sizemore

    Size(more) Doesn’t Matter

    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

    Crash Guest Dummy

    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

    Tabloid Trash

    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

    Assanova

    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

    Operation Keep It in His Pants

    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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