1. Eugene Robinson’s Man of the Year Award
The Atlanta Falcon’s Robinson had a sterling reputation in 1999. A devoutly religious man, he donated money and time to his native inner-city Hartford. To sum up, all of this led to him receiving the Bart Starr Award. An annual award, it’s a commendation of exemplary character and leadership.
So, of course, that same night, he tried to solicit oral sex from an undercover officer. He didn’t sleep well that night and played terribly in the Super Bowl the next day. Then he returned the Bart Starr award to the NFL. In short, this hilarious misjudgment is one of the greatest moments in Super Bowl history and incredibly embarrassing for everybody involved.