Couple Nickname: None
Dated Between: 2004 - 2006

Everyone knew from the get-go that Britney Spears and back-up dancer Kevin Federline's relationship was destined to end badly, but it was really hard to anticipate just how badly. Britney was still pop's princess at the time, fresh from her break-up with Justin Timberlake that devastated teenaged girls everywhere, and Kevin just didn't look like her type. At all.

Additionally, Kevin and Britney's relationship began very shortly after Kevin broke up with the mother of his first two children, Shay Jackson. In fact, he was already with Britney when Jackson gave birth to her second child with Federline.

Spears and Federline's relationship was undoubtedly the beginnings of Spears' downward spiral. The tabloids were hounding them 24/7, the two co-starred in a reality show together that featured badly recorded home movies from the couple called Chaotic, and the two got engaged after only three months.

Two years and two kids later, Spears filed for divorce, and it wasn't much later that she was shaving all of her hair off, beating up cars with umbrellas, and being hospitalized for drug abuse.