25. J.R. Rider

Sport (Years Played): Basketball (1989-2001)
Accolades: 1994 NBA Slam Dunk Contest Champion, 2001 NBA Champion

Before he flamed out (zing) due to various off-court problems, Rider was a decent NBA player, averaging more than 19 points four times in his truncated career. But it's no secret that rap sheet was more extensive than his stat sheet back in the day. Most of his run-ins with the law were marijuana-related. He was arrested for possession twice in 1996 then another time in 1998 when police saw him in his car smoking marijuana out of a soda can (SMH, really?). Things got so bad that the league even demanded he seek counseling when he reportedly was seen smoking weed at an Orlando hotel during the 1999-2000 season. Getting high on the court? Dope! Off of it? Not so much. #punsonpunsonpuns