Men
Bertram Cooper
Bert Cooper likes to cultivate the image of an old eccentric in the offices of Sterling Cooper (and later, at Sterling Cooper Draper Price), but beneath the affection for Japanese art and Ayn Rand quotes lies a sharp, ambitious mind. He’s perfectly happy to keep and use secrets to manipulate other members of the firm, whether it’s using Don’s real identity against him or not-so-subtly reminding Robert Sterling just who exactly it was who got him his job in the first place.
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.
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.
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.
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.