Scottie Pippen vs. Charles Barkley 

Pippen's Notable Sneakers: Nike Air Maestro, Nike Air Flight Lite Mid, Nike Air Max Uptempo
Barkley's Notable Sneakers: Nike Air Force Max, Nike Air Force 180 Low, Nike Air Max 2 CB 4  

Years: 1987 - 2000 

After Mike and Penny, Barkley and Pippen had the most recognizable signature lines in the league. During a few face-offs in the Finals and All-Star Game they rocked some of Nike Basketball's classic '90s kicks before teaming up in Houston and failing to get that ring as one of the NBA's first trade/free agency Big Three.