48. Jessica Simpson

Age (circa 2009): 29
Occupation: Singer/Actress

Yeah, Jessica Simpson is dumb, and yeah, she's produced a steady stream of crappy music, movies and reality TV over the last decade, but she's got twos even her own daddy is excited about and it's kinda fun to smash hot ditzy blonds. Word to Stacy from accounting.

AUGHTS ACHIEVEMENT:
Jinxing the Dallas Cowboys. Other than that, her video for "These Boots are Made for Walking."