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Bill Haverchuck

Bill Haverchuck is one of Sam Weir’s best friends in the cult classic Freaks and Geeks. Though he is picked last in gym class and is bullied in the halls, he seems the most secure with who he is and is in no hurry to grow up. To really polish off Bill’s look, dig out the oldest sneakers in your closet and bring back that terrible posture you’ve learned to forget.

Saul Silver in Pineapple Express

James Franco plays pot dealer Saul Silver. A roach containing his strain of marijuana, Pineapple Express, gets left at a murder scene, and hijinks ensue. The rest of his outfit might be classic stoner wear, but check out the chrome on his wrist.