1. Cheech & Chong
From Up in Smoke through Next Movie and Nice Dreams, Cheech & Chong represent the ’70s at its stoniest. Still in jail for bong sales, Chong has a recurring role on That ’70s Show. Cheech Marin has had a long movie career and teamed up with Don Johnson on Nash Bridges.
2. Sean Penn
His portrayal of high-school stoner Jeff Spicoli in Fast Times at Ridgemont High is a cannabis classic. With Falcon and the Snowman, Carlito’s Way, and Hurly Burly, Penn turns to harder drugs. He had a big year in 2003 with 21 Grams and Mystic River.
3. Dennis Hopper, Peter Fonda & Jack Nicholson
These three Hollywood icons appear variously in The Trip, Psych-Out, and Easy Rider, a psychedelic trilogy that’s never been matched. All have had memorable movie careers (Hopper in Blue Velvet, Fonda in Ulee’s Gold, Nicholson in One Flew Over the Cuckoo’s Nest), but no more so than the man they simply call "Jack."
4. Dave Chappelle & Jim Breuer
The Half Baked duo are up there with Cheech & Chong. Chappelle reprises his "weedy" character in Undercover Brother and is currently starring in Chappelle’s Show. After a memorable stint on Saturday Night Live, Breuer went back to standup comedy.
5. Johnny Depp & Benicio Del Toro
Graphic adaptation of Fear & Loathing in Las Vegas is fertile ground for the Depp’s Hunter S. Thompson and Del Toro’s deranged Dr. Gonzo. Depp does coke in Blow, eats peyote in Dead Man and smokes opium in From Hell, and has received kudos for his Keith Richard-influenced portrayal of Jack Sparrow in Pirates of the Caribbean. Del Toro won an Oscar for Traffic and is nominated for 21 Grams.
6. Marlon Wayans
This Wayans brother pushes the weed envelope as Shorty in the first two Scary Movie installments. His next movie is White Chicks.
7. Rory Cochrane
Notorious for his role as stoner Slater in Dazed and Confused, Cochrane followed up with Love and a .45 (opposite Renee Zellweger) and now plays a cop on C.S.I.: Miami.
8. Chris Tucker
As Ice Cube’s stony sidekick in Friday, Tucker’s high-voiced, fast-talking Smokey steals the show. He’s appeared opposite Jackie Chan in the Rush Hour series.
9. Eugene Levy & Rick Moranis
SCTV originals Levy and Moranis stumble upon a huge bag of ganja in Club Paradise. Known best for his roles in the America Pie series and Bringing Down the House, Levy’s also regular cast member in Christopher Guest films (A Mighty Wind, Best in Show). Moranis co-starred in Honey, I Shrunk the Kids and Little Shop of Horrors, and with Dave Thomas is half of another infamous comedy team: SCTV’s Bob and Doug McKenzie.
10. Diane Keaton
Woody Allen makes fun of Keaton when she smokes pot in Annie Hall. Last year the much-decorated actress starred opposite Nicholson in Something’s Gotta Give.
Al Pacino in Scarface, Serpico, and Carlito’s Way
Snoop Dogg in The Wash, Baby Boy, and Bones
Jason Mewes in Jay and Silent Strike Back, Dogma, Mall Rats, and Clerks
Method Man & Redman in How High
Jeff Bridges in The Big Lebowski
Bridget Fonda in Jackie Brown
Brad Pitt in True Romance
Paulo Costanza in Road Trip
Ice Cube & Don "D.C." Curry in Next Friday
Owen Wilson in Zoolander and The Royal Tenenbaums
Pee Wee Herman in Blow
Marisa Tomei in Four Rooms
Ari Gold in Groove
Ashton Kutcher & Seann William Scott in Dude, Where’s My Car
Pauly Shore & Sean Astin in Encino Man