Most Beautiful Heartbreaker
Billy Crudup

Most Beautiful Feuding Foodies
Ex-lovers Matthew Kenney and Sarma Melngailis

Most Beautiful Working Heiress
Aerin Lauder Zinterhofer

Most Beautiful Jailbird
Lil’ Kim

(Photo credit: Clockwise from top left: Patrick McMullan; Zack Seckler/Getty Images; Stan Honda/AFP/Getty Images; Wireimage)