Cheech & Chong (Played by Cheech Marin & Tommy Chong – Various Films)

Although often in character, the screen personas of these comedians are pretty close to the fellas themselves. A laurel and hardy for the love generation, hippie and Cholo, they left an indelible mark. The original crossover stars from an era where pot was a certified tool of the counter culture. If the action had been at modern strength it’s highly likely that their productivity might have sagged. However, through a string of hit films and comedy albums, Chong and Marin were able to keep filling the bong of their comedy with fresh enough water long enough to make millions, become icons, and get cast by Scorcese.

Kenny (Played by Harlan Williams – “Half Baked”)

The absurdist comic found his niche for a period as a wacky character actor, perhaps cut short by the abysmal failure of his starring vehicle “Rocket Man.” He is most notable for his role in “There’s Something About Mary,” however Kenny has some of the best moments in this Chappelle/Brennan masterpiece. Every character in this movie could wind up on this list, but there is just something about Kenny that makes him shine a little brighter, probably the scene with the horse. Definitely the scene with the horse. See clip below:

Jeff Spicoli (Played by Sean Penn – “Fast Times At Ridgemont High”)

For the 80’s generation, there was nobody who typified the stoner ethos or California cool better then Sean Penn’s surfer dude. He informed everything from Bill & Ted to the very idea of grungy 90’s slacker culture. Sean Penn was in his Madonna dating, paparazzi punching, party animal phase, but channeled nothing but joy, glee, and wide eyed wonder. Sean Penn moved on from playing stoners to getting Cartel bosses indicted, but this is a window into a simpler time when tasty waves and a cool buzz would leave anybody feeling fine.

Smokey (Played by Chris Tucker – Friday)

Chris Tucker made a mark on the culture and forever cemented that people would be quoting his “It’s Friday, ain’t got shit to do…” line, but almost every punchline or scene button that his character has will be quoted in rap lyrics, basements, stoops, decks, and smokers circles for all eternity. He plays the perfect clown to Ice Cube’s straight man, in a magical formula that Method Man and Redman tried for decades without even coming close to replicating.

Raoul Duke (Played by Johnny Depp – Fear & Loathing In Las Vegas)

Saying that this character is a stoner is like saying that Lebron James “plays ball.” Hunter S Thompson’s alter ego as glorified by Terry Gilliam and Johnny Depp was the result of an immersive research process that nearly cost Depp his sanity. This character takes most mind altering substances that exist through the narrative of this movie, which although sensational and hallucinatory, barely scratched the surface of what really happened.