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Joanna from Office Space
Joanna is a Chotchkie’s waitress played by Jennifer Aniston in Office Space. She gets constant grief from her manager for not showing enough spirit. Sure, 15 pieces of flair is the minimum, but it’s up to you if you wanna just do the bare minimum.
Milton Waddams
Milton is a meek employee of Initech. He’s walked all over by the management, with VP Bill Lumbergh taking his cherished red Swingline stapler and moving his cubicle into the roach-infested basement. But Milton will have his payback.
Don Draper
Don Draper is the all-American success story: a self-made man with a job at a top New York advertising agency, a house in the suburbs, and a beautiful wife. Well, if you ignore all the identity theft, manslaughter and adultery that got him there. Thus, not included in the costume below: self-loathing, borderline alcoholism, Dick Whitman.
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.
Crimson Viper
Crimson Viper, also known as Maya, is definitely one of video game’s sexiest females. She wears the suit because she’s a secret agent under the employment of a U.S. government agency. But don’t let her beauty fool you – she conceals weapons in her boots and her gloves are electrically charged, making her a deadly threat.