Thomas "Hollywood" Henderson

Where: Super Bowl XIII, Miami (1979)
Incident: Throughout his career, Henderson had a reputation for being a bit of a badass party animal. But he took his love of the life to new heights when he decided to go skiing—on the sidelines. Tucking an inhaler of liquefied cocaine inside his uniform, Henderson couldn't stop the Cowboys from losing to the Pittsburgh Steelers 35-31.
Result: Hollywood is proof that throwing away your football career and doing a two-year bid because of cocaine can in fact lead to happy ending as he won $28 million in the lottery in 2000. Damn, we need a movie about this starring Will Smith, super stat.