Ray J and Kim Kardashian Cozy up on the Set of His Music Video in Hollywood on July 16, 2005
Unless you've been living under a rock, you've probably heard of the Kim Kardashian sex tape. Well, Ray J is the guy in said sex tape — and probably the man who came up with the brilliant idea of filming their under-the-sheets escapades in the first place. (We're sure Kim is oh-so-grateful.) After the tape was "leaked" in February 2007, she sued Vivid Entertainment for ownership and eventually settled with them for $5 million.
Beyond his self-made porno career, Raymond Norwood Jr. is Brandy's younger brother, Snoop Dogg's first cousin, a reality star, actor, and R&B crooner. He and Kim dated on and off from 2003 to May 2006, when she was spotted out and about with Nick Lachey. After rekindling their romance in July 2006, she and Ray J ended things (yet again) a couple months later. The reason for the breakup? Nick Cannon.