9. Macauley Culkin — Reebok Pump Battlegrounds

When: 1992

Where: Promo Shoot With Two Other Kings

All we can think of when we look at this photo is the incredible amount of shit Mike must have given Macauley off-camera for wearing Reeboks. Bold move by the little man, no matter how popular he was at the time. What, what did you think we were going to say?