Career: 1981-1993, 1995-1998, 2001-2003
Cockiest Quote: "There is no 'I' in team, but there is in win"
Everyone knew Michael Jordan was going to make damn near every clutch shot he took‚-including himself. He was cocky because he was the best and could not be stopped. Mike relished a challenge. He once made a free-throw with his eyes closed for Dikembe Mutumbo and shrugged off an NBA Finals record six straight threes. When he was cut from his high school team as a sophomore in favor of his buddy Leroy Smith because of his height, he made it his business to get better. After he retired the first time, his first words on his return were simply, "I'm back." Whenever he told cats he was gonna drop 40, he would drop 40. Cocky? Watch his Hall of Fame speech and you'll understand.