19. Eugene Robinson
One of the few Super Bowl moments on this list, Robinson ensured notoriety for life by soliciting an undercover police officer disguised as a hooker the night before the biggest game of his life. After Robinson discovered that he unfortunately had not encountered a prostitute, he spent the night at the local precinct. Meanwhile, this came after he won the Bart Starr award for good character. Needless to say, he handed that back following his release.
Then came the game itself. Dan Reeves made the ridiculous decision to start Robinson after his night from hell and maybe should be on this list instead. The corner tarnished his reputation first and foremost by trying to hook up with a hooker but played terribly to make things even worse. The worst moment was when Robinson gave up a 70-yard touchdown. In sum, it was the worst weekend of his life.