46. Brett Favre
Cockiest Moment: Pics sent to Jenn Sterger
Brett Favre fired footballs through tight spots with reckless abandon. His style as a win-some-lose-some-win-some-more gunslinger garnered him the NFL records for all-time touchdowns and interceptions. But as cocky as he was on the field, he was down right ballsy off of it, so to speak. During his time with the Jets he sent some seemingly unprovoked wiener pics to a Jets staffer. He was like Joe Namath If Broadway Joe had a camera phone in 1969.