Sport: Boxing
Career: 1988-Present
Cockiest Quote: “I was knocking guys out in the streets before I knew how to throw a jab and keep your chin down."

All great boxers are cocky—you have to believe in yourself if you're gonna take your shirt off and fight another man in front of thousands of people—and B-Hop is no exception. And Hopkins backed it up, too: After losing his first professional bout in 1988, he went 17 years without losing to anyone not named Roy Jones, Jr. In addition to a healthy self-regard, Hopkins also has some interesting views on race, including the idea that Manny Pacquiao would be susceptible to a "slick" black fighter, and telling Joe Calzaghe that he'd never let a white boy beat him (alas, he did). Hey, even if you don't always agree with them, at least cocky athletes make it interesting.