Men

Harry Crane

Despite his numerous bowties and horn-rimmed glasses, Harry, like many of the characters on Mad Men, is not as old-fashioned as he appears. While most of his fellow copywriters at Sterling Cooper are still concentrating on magazine adverts, Harry is looking to television as the way of the future. After creating and running the department at the old firm, it’s no wonder that Don and company seize the chance to swipe him for the newly formed Sterling Cooper Draper Price.

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.

Cheech Marin

Cheech Marin is one half of the cannabis-driven comedy duo Cheech & Chong. In “Up In Smoke”, Cheech stars as Pedro De Pacas, who — not too surprisingly — is a stoner desperate to procure another stash.

Willie Nelson

Willie Nelson is one of the most recognizable country singer songwriters today, equally famous for his hit records and his activism for legalizing marijuana. The government can sell his things, but they best not touch Trigger, his beloved guitar.

Steve Urkel

Steven Q. Urkel, played by Jaleel White, lives next door to the Winslows on the TGIF show Family Matters. Urkel is the ultimate nerd with his awkward fashion, high-pitched voice, and unrequited love for Laura Winslow — at least until he drinks his cool juice and transforms into Stefan Urquelle.

George Michael Bluth

George Michael is the reserved teenage son of Michael Bluth, with an equally reserved sense of style. Despite his family’s wild antics, he just wants a normal life for himself. Oh, and to have his cousin Maeby love him back.

Annyong Bluth

Annyong is the adopted Korean son of Lucille and George Bluth. Knowing no English, he repeats only “annyoung” — the Korean word for “hello” — and the name sticks. He quarrels with his brother Buster and is revealed to be a mole seeking revenge on the Bluth Family.

Jeffrey “The Dude” Lebowski

Jeffrey Lebowski (Jeff Bridges), or as he would prefer to be called, the Dude, is an avid bowler and otherwise total slacker. He gets caught up in a kidnapping scheme after getting confused with millionaire Jeffrey Lebowski. That sweater really ties the outfit together, Dude.

Anton Chigurh

In No Country for Old Men, Anton Chigurh (Javier Bardem) is a cold-blooded killer with a strange appearance and stranger weapon of choice. He also plays a mean game of heads-or-tails. Call it, friend-o.

Silent Bob

If you’re interested in chain smoking and silence then Silent Bob is your man. The other half of Kevin Smith’s duo, Jay and Silent Bob, he is one of the few people that has managed to make wearing a duster look kind of cool.