When you're as iconic in the entertainment industry as Britney Spears, it's hard to keep your love life under wraps. And the pop princess has definitely had her fair share of famous boyfriends -- do the names Justin Timberlake, Fred Durst, K-Fed and Criss Angel ring a bell?
Howie Day (2007)
Britney Spears entered rehab in February 2007, and -- in true Britney fashion -- she didn't stay single for long. The pop songstress reportedly began dating singer/songwriter Howie Day shortly after the pair met at the Promises rehab center in Malibu, Calif. but a concerned Lynne Spears reportedly tried to end the relationship after learning that Day had previously been arrested.