Worst Performances: Urban Legend (1998), American Pie (1999), Josie and the Pussycats (2001), American Pie 2 (2001), National Lampoon's Van Wilder (2002), My Boss's Daughter (2003), Alone in the Dark (2005)

Before she lost her way and turned into a poster girl for plastic surgery mishaps, Tara Reid was once every high school boy's fantasy girl: that hot blonde who's also nice and approachable. Credit her role in 1999's teen comedy smash American Pie for that. However, any of those smitten lads who took a step back and really looked at her American Pie performance, not to mention her work in subsequent flicks Josie and the Pussycats and National Lampoon's Van Wilder, no doubt realized that she's the B-list queen of vapidness.