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If you ask me, the apex of twentieth century comedy was reached during Cameron Crowe’s 1982 coming-of-age masterpiece, Fast Times at Ridgemont High. Sitting in his room, smoking a bong, discussing brain damage with his shaggy haired compadre, Jeff Spicoli (played by Sean Penn) pulls out a brand new pair of Vans slip ons and begins to bash his head with the waffle sole to show off to his equally as blitzed out friend just how mentally numb he was. We could discuss the timeless humor of a stoned out kid bashing his own head in, or number of brain cells that Spicoli discarded that day, or the slapstick origins of his cranial abuse, but for today, I’m more concerned with Spicoli’s Vans.

Spicoli’s checkerboard slip ons have become the stuff of legend, and dare I say that never before has an actor’s footwear so completely captured the spirit of his character. Even the name “slip on” reflected Spicoli’s attitude, which was many steps beyond devil-may-care, in devil-may-get-high-off-brain-damaging-weed territory. Since ’82, slip ons fortunately have lost their THC-laced reputation as shoes for stoners, but it wasn’t until recently, that they registered on the menswear radar.

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