10. Keith Richards
Following his cameo role in last summer's Pirates of the Caribbean: At World's End, the acting bug bit Richards so hard that he actually knocked out his back molars in the hopes of playing the titular character in the big screen remake of Mister Ed. We'll be there with drugs and his dad's ashes to console Richards when he learns Hollywood's put a halt to the talking horse project in order to focus on the 10th installment in the Air Bud series.
9. Thom Yorke
Here's a little-known piece of trivia: Radiohead's seminal, 1995 album The Bends was actually named after Thom Yorke's mangled mouth.
8. Paul Wall
Wait, is Paul Wall a James Bond villain? Actually, no, Wall's a Houston-based rapper and jeweler best known for casting his teeth with a golden grill. Which raises a good point: grills look stupid.
Since ol' Madge has always hired the best producers to reinvent and resuscitate her career, you'd think she'd have enlisted a good orthodontist to close that mysterious gap in her front teeth by now. Perhaps she's been too busy focusing on her burgeoning directorial career.
Be it a lifetime of hard living or the simple birthright of being British, most people on this list have an excuse for bad teeth. Jewel, a squeaky clean Mormon from Alaska with the corny lyrics of a 14-year-old girl, should have invested in some dental work and fixed up that snaggle tooth as soon as she went platinum. Now that her pop career has gone bust, maybe her hillbilly teeth will fare better in Nashville.
5. Mick Jones
Did former Clash guitarist Jones not get the memo that Austin Powers jokes have been played out for years now? Take out the novelty teeth, dude, and start working on your Boratisms.
4. Trick Daddy
Did we mention grills are stupid? But in Trick Daddy's case we'll let it slide. Heck, the grimacing, over-the-hill rapper's gotta hold unto something resembling platinum
3. Young David Bowie
He used to live in England and have bad teeth, and now he keeps a place in America and has a solid set of pearly whites. He also used to bone dudes, and now he's married to supermodel Iman. Can you say total makeover?
2. Amy Winehouse
Just leave the poor girl alone, OK? It's not like you're her dental hygienist or something. Besides, ol' Amy's got a perfect excuse for that missing tooth: She had to pry it loose, as her gums are the only place left on her body that will willingly accept drug injections.
1. Shane McGowan
Anyone who actually looks better without their teeth has to top our list of mangle-toothed rockers. Though years of alcohol and substance abuse have left infamous Pogues frontman Shane McGowan with little more than a crooked picket fence of bottom chompers, back in his heyday the dude's fang-like front teeth were so gnarly and underdeveloped they looked like two aborted fetuses.
whaaaaaat no Pete Doherty? wtf this list was practically made for him idgi