Played By: James Van Der Beek and Michelle Williams

OK, so everyone Dawson dated instantly landed on our shitlist, not because of envy, but because of the fact that Dawson Leery was arguably one of those most annoying characters in the history of teen television. Former "city girl" Jen Lindley just happened to bring out the most obnoxious in him—the first time in season one, when he called his then-girlfriend a "slut" in a jealous rage, and the second time in season five, when he became a sick, clingy puppy after losing his virginity to her.