Significant Sneakers: Nike Zoom Flight 95, Nike Air Max Uptempo, Nike Blazers

Brent Barry had a lot to live up to both in a basketball sense and sneakers, considering his pops is on this list too. Brent pretty much set his name in (sneaker) stone by winning the Slam Dunk Contest in his rookie season while wearing the Nike Zoom Flight 95. He would go on to play in a handful of Nike Basketball classics. If that wasn't enough, he also busted out a pair of Paul Brown Nike Blazers for the 3-Point Shootout in 2003. Gangsta.