3. Enid & Seymour (Ghost World)
It's a pretty safe bet that - before he met Enid - Steve Buscemi's Seymour character in Ghost World did not get a lot of sex. There's something incredibly cool about Buscemi in real life, but he's your go-to guy for nerds, freaks and oddballs when it comes to the motion picture scene, because you can't play romantic leads with a face like that. In the 2001 comic book adaptation he plays a little of everything as a socially inept, shy and timid jazz record collector. Enid, on the other hand, is a contriving little b*tch who totally uses Seymour for her own ends, which leaves the poor guy totally smitten and obsessed. He's the quintessential ugly guy who somehow gets with a hot chick and spends the rest of his life punching above his weight class. As sad as this tale is, though, Seymour ultimately becomes a legend amongst his peers having been the only person in his group of friends that managed to go all the way with someone way hotter than themselves. Seymour, we salute you.