14. Sean Avery
Career Years: 2001-2012
Career Lowlight: Infamous "sloppy seconds" comment about Elisha Cuthbert.
Avery has been quite eccentric throughout his time in the NHL, and is seemingly always at the center of some off-ice controversy. Over the course of a 12-year career, he has had a rule named after him, called another player's girlfriend his "sloppy seconds," been accused of hurling racial slurs at players, and has been an intern at Vogue. He couldn't even retire like a normal person; he was sent home from his AHL team in March of 2012 and has yet to formally announce his future plans.