[60] MALCOLM GLADWELL
Point tipper Sideshow Bob with a classier library card and a desk at the New Yorker. |  |
[59] GENE SIMMONS
Reptilian entrepreneur An unsexy icon for three decades, Simmons has long been the butt of jokes about how KISS were far scarier during the years when the makeup came off. Tongue-lapping antics, which Gene has long considered a sign of his virility, are now considered sexy only by prepubescent boys who’ve recently discovered Hustler. Now that he’s reprising his schtick as a reality-show dad, a little advice: the tongue’s not hot when it’s uncoiling from a face that could be shilling Sea-Bond denture cream. |  |
[58] JACK ABRAMOFF
Disgraced, sleazy bribe artist Flabby, amoral lobbyist at the center of numerous evil scandals that ran the gamut, from defrauding Indian casinos to granting dictators access to President Bush.
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[57] RANDY JOHNSON
Buzzardly hurler He was number two on our list in 2006, but women gave him a second look this year. Perhaps because he got traded from the Yankees to the Diamondbacks? (Couldn’t hack it in the big town, Randy? Suck it up, broseph: we found it much easier and more enjoyable to hate you in pinstripes.) |  |
[56] KIM JONG-IL
Dear leader Though this deranged North Korean demigod has a certain cherubic look — he could almost pass for a beatific Macy’s Thanksgiving Day float — he’s rumored to be quite the porno connoisseur, as well as a binge drinker and womanizer. Which makes us all feel so much safer about his nukes. |  |
[55] RONALDINHO
Goal getter The world’s greatest soccer player is so ugly, even his action figure has buck teeth. Kissing him must be like getting kicked in the face by a donkey. |  |
[54] DR. PHIL
Boob-tube windbag Two parts smug empathy, six parts self-satisfied gloat, this unsolicited life coach to the universe has all the charm of flatulence in a bathtub. |  |
[53] BUD SELIG
Baller, shot-caller Toupee-wearing, fashion-challenged MLB commissioner could not look more like a Midwestern former used-car salesman — mainly because he is a Midwestern former used-car salesman. |  |
[52] JAY-Z
El presidente Though practically married to one of the most beautiful women in the world, Jigga was red-flagged for unsexiness by our panel of judges. (The male members of the editorial staff want it made clear that they stood up for Jay, and plead with him not to hurt us. See #76.) Our favorite comment about what makes Jay unsexy? One young woman opined, “It’s like he’s got a lazy eye, only it’s his whole face.” |  |
[51] ANTHONY CUMIA
Radio harlot It was a tough call to pick just one of the unimportant, greasy co-hosts of the Opie and Anthony Show, since women are nearly universally allergic to both of them. Anthony wins by a (misshapen) nose, a pencil neck, a scraggly steel-wool excuse for a haircut, and a goatee that went out of style back in 1994. |  |
