Richardson is a talented forward/shooting guard for the Orlando Magic, as well as the one-time Knick and fiancé of R&B singer Brandy.

Richardson was a college star for DePaul University, leaving after his sophomore season when he was picked by the Los Angeles Clippers in the first round of the 2000 draft. After four seasons with the Clippers, he signed as a free agent with the Phoenix Suns in 2004. He was a key player on a loaded Suns team that year, winning the NBA Three-Point Shootout in the process. He was traded to the Knicks in 2005. Richardson is a natural scorer, and many believe that in the right situation he could put up over 20 points per game. But on a Knicks team that featured a number of ball hogs—Stephon Marbury, Steve Francis, and Jamal Crawford, to name three—it's been difficult for him to make his mark. After four years in the Big Apple, he spent a year with the Miami Heat pre-Lebron James, and found himself on the Orlando Magic in 2010.

Richardson was once engaged to R&B singer Brandy, reportedly giving her an 11.5 carat, $1 million engagement ring when he popped the question in 2004. The two split up in 2006, and the National Enquirer reported that Brandy's subsequent car accident—which killed a California woman—happened just hours after Richardson dumped her for good. (Brandy also reportedly got a tattoo of Richardson's face on her back changed into the image of a cat.) [Image via Getty]