[58] CRAIG NEWMARKLOATHSOME LISTER
Craigslist > Boston/Camb/Brook > Missed Connections. You: all over the Internet, offending every sensibility of graphic design, beginning every blog post with the word "Hey." Us: still smarting about our classifieds business going up in smoke, marveling at how creepy a goatee can make a balding guy with glasses look. Let's not meet again — ever.
[57] JUDAH FRIEDLANDERHOMELY HIPSTER
The resident troll of TV's 30 Rock hides under trucker hats festooned with ironic slogans. And while he seems amusing and harmless enough, his greasy mullet and "I totally just ate a booger" vibe still trigger our gag reflex.
[56] FRED PHELPS JR.UN-CHOSEN ONE
Phelps was already infamous for his role as the leader and chief bigot of the hate-mongering Westboro Baptist Church (its contribution to religious thought: the phrase "God Hates Fags"). Not content merely to protest the funerals of American servicemen in Iraq, Phelps recently protested at Heath Ledger's funeral, condemning the actor for his role in Brokeback Mountain. Hey Fred: if God loves you so much, why'd He wallop your whole family with the ugly stick?
[55] MEL GIBSONSAUCY AUSSIE
Gibson's got a brutal streak, lacing his movies with carnage and torture. But then again, would you expect any less from a homophobic Holocaust denier with alcohol issues?
[54] BILLY RAY CYRUSSTAGE DAD
Sure, your babygirl Miley has single-handedly kept the music industry in business these past two years. But what kind of achy-breaky stage dad bum-rushes his tweenybopper daughter's career to throw his hound-dog mug back in the limelight? And why — dear God, why? — the soul patch?
[53] MICHAEL VICKK-0 KILLER
Well, now we know who didn't let the dogs out.
[52] CRISS ANGELABRA MASCARA
If he's so handy with his wand, how come he can't date anything more sentient than a heavily medicated pop star? This prestidigitating poseur tries to pull off the glam look, but always ends up looking like a tranny.
[51] DMXTUNED-OUT RAPPER
America doesn't ask much of her citizenry. Pay taxes, perhaps cast a text vote for an American Idol contestant. But in return, she hopes that, on the most basic of levels, her children are at least paying attention. Particularly her celebrity children. So when DMX revealed in an interview that he not only had never heard of Barack Obama, but then also broke into fits of laughter at the Illinois senator's name, America had every right to think that the rapper was something of a complete douche.
[50] MARK ZUCKERBERGZOMBIE/VAMPIRE/WEREWOLF
It's not just that Facebook sucks. In the wake of the embarrassing Beacon/privacy flap, Facebook is like the crazy ex-boyfriend who stalks you and posts nasty sleaze about you on the Internet. We blame "founder" Mark Zuckerberg, the Ivy League twerp, who may or may not have stolen Facebook's source code from his Harvard classmates (the case is still tied up in a Boston Federal District Court), and who looks, not coincidentally, like he took a book in the face.
[49] "DR." ROBERT JARVIKARTIFICIAL HEART-ON
Even before Lipitor recalled his ads (the "doctor" isn't licensed to practice medicine, and his claim of having invented the artificial heart is, at best, exaggerated), Jarvik had already become the year's creepiest TV spokesdude. His ghoulish face suggests a clammy "If They Mated" Conan O'Brien sketch between George W. Bush and Riff Raff from The Rocky Horror Picture Show — the perfect representation of Big Pharma run amok.
