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?
Jared Leto (rumored; 2003)
The rumor mill really started churning later that year, with Britney Spears reportedly dating Jared Leto at one point -- which would have wreaked all kinds of Tinsel Town havoc since Spears' ex Justin Timberlake was dating Leto's ex Cameron Diaz at the time. The singer laughed off the rumors, however, saying that she and the actor were just "really good friends."