16 of 16Fergie and Justin Timberlake
Long before either of them made it big, the pair dated in the late '90s when Fergie's girl group Wild Orchid opened for 'N Sync. "He was 16 and I was 23," Fergie recalled to Australia's Courier Mail. "It was right before he got real heavy with Britney [Spears]."
Photo By: Chris Polk/FilmMagic