Movies
Bill Lumbergh
In Office Space, Bill Lumbergh is an Initech manager who constantly harps on Peter Gibbons about his TPS reports. If you could just go ahead and pick either the suspenders or the belt, that’d be great, mmmkay?
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.
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.
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.
Jay
With his foul mouth and fondness of marijuana, Jay made his presence known in many Kevin Smith films as one half of the duo Jay and Silent Bob. His style is much like his attitude, laid back with no concern of what others think about him. Snoogans!
Eli Cash
From the Royal Tenenbaums: The crickets and the rust beetles scuttled among the nettles of the sage thicket. “Vamanos, amigos,” Eli Cash (Owen Wilson) whispered and threw the busted-leather flint craw over the loose weave of the saddle cock. And they rode on in the friscalating dusk light.