Who: Karl Malone
On the court Malone may be one of the best to hold down the four-spot but his personal decisions have always been a bit odd. After he left the league he decided to endorse Skechers Shape-Ups, a shoe synonymous with middle-aged women who loathe working out. (You can bet Malone earned his own physique the old-fashioned way.) We don't care how short Stockton's shorts were, he has more street cred than Karl after this one.