I've put way too much thought into this list - the only problem is that there's not a whole lot to choose from. They play an important part in Intolerably Cruelty, to be sure, and they're so pivotal in one film that the film is even named Teeth, but a) I haven't seen that, b) it sounds too gimmicky, and c) I'm not even sure they show the titular teeth because d) they ain't in her mouth.
What I was aiming for were the five most memorable teeth, be they an individual tooth or a mouthful. Obviously, vampires are way too commonplace and boring. Before we go any further, how about a lifetime achievement award to Tom Cruise, owner of three front teeth (or one, depending on how you look at it). Ever since this was pointed out to me, I've been unable to not fixate on it (don't think about elephants), so I thought I'd share my trauma with you:
Next, an honorable mention.
Mike Myers, Austin Powers series: Austin's gritty, grimy Briteeth were an important element of his character, and though they're not amongst my favorites, they deserve a shout-out. Sexy, baby:
5. Matt Dillon, There's Something About Mary: The definition of "chompers." Dillon's Pat Healy will do whatever it takes to get in the good graces of Mary, and when he learns that she's into nice, big teeth, well...
4. Vinnie Jones, Snatch: Really, the tooth itself is pretty inconsequential to the film; it merely adds to the aura of cool that writer/director Guy Ritchie imports into his characters and movies, and Tony was most definitely a cool cat and a bad ass, and his bullet tooth certainly helped in that regard.
3. John Matuszak, The Goonies: What would you work on first - the severe facial deformity or that set of mismanaged rice bits? Poor Sloth...
2. Richard Kiel, The Spy Who Loved Me and Moonraker: I can't imagine what it must have been like to brush those things after chowing down on some popcorn. That in and of itself is a nightmare.
1. Chris Cooper, Adaptation: It's a travesty that for my favorite set of teeth, there was not a single good image to be found on the internets. I had to find a video clip and screenshot it to present you this look at the few remaining teeth that John Laroche had. I don't doubt at all that his mouth played a large part in his Oscar win.