Charles Barkley vs. Michael Jordan

Barkley's Notable Sneakers: Nike Air Max Force, Nike Air Force 180, Nike Air Alpha Force II, Nike Air CB 34
Jordan's Notable Sneakers: Air Jordan 1 through VIII, Air Jordan XI through XIV 

Years: 1985 - 1993, 1995 - 2000 

Two of the strongest forces on Nike's roster since the mid '80s — the brand wouldn't be what it is today in basketball without Chuck and Mike. Charles' Air Max infused sneakers were always hot on the streets but Jordan was Jordan. Barkley just couldn't top him, despite repeated attempts.