Nike Air Force Max "Black/White" vs. Air Jordan VIII "Playoffs" 

Players: Charles Barkley vs. Michael Jordan
Year: 1993

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.