19. Xander (Buffy the Vampire Slayer)
Though Xander starts off the series as being a geek with a fruitless crush on the titular heroine, over the course of the seven seasons of the show, he grows up and becomes nearly cool. He manages to hook up with Willow, Cordelia, Anya and Faith over the course of the series. He even nearly closes the deal with Buffy herself in the episode Bewitched, Bothered and Bewildered on account of some witchery. Of course, things don't always come up roses for Xander. He almost married a vengeance demon. He has military flashbacks, despite technically never having served in the army. And worst of all, when he has a run in with Nathan Fillion's preacher, he gets one of his eyeballs plucked out. But regardless, we'd all love to see a spinoff with Xander, who managed to be the cynical and sarcastic voice of reason throughout the show.