38. More Stylish Than Zoolander
Movie: Heavy Weights
Sneaker: Nike Air Huarache Light
'Heavy Weights' is an unremarkable kid's comedy that's only good for Valium-addled transatlantic flights, but it's notable for two things — an early Judd Apatow writing gig and Ben Stiller in proto 'DodgeBall' jerk mode wearing the cult classic Air Huarache Light in the grape colorway. The sneaker's reputation has eclipsed the movie it made a cameo in.