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The High Life of Jeff Spicoli

Sean Penn’s stoner from ‘Fast Times at Ridgemont High’ is a quintessential teen movie character—and not just because of the copious amounts of pot he smoked

Universal Pictures/Ringer illustration

On October 12, 2011, James Van Doren, the designer of the first Vans sneakers, died at the age of 72. A month later, a teen movie found its way into the opening paragraph of his New York Times obituary. Tracing the popularity of Van Doren’s flagship shoe, the newspaper concluded that the fad started in 1982, “after Sean Penn wore a black-and-white-checkered pair in the movie Fast Times at Ridgemont High.”

At one point in Fast Times at Ridgemont High, after taking a giant bong hit in his Playboy centerfold–covered bedroom, Penn’s character lifts one of his Vans out of its blue box, smacks himself in the forehead with its rubber sole four times, and shouts, “That was my skull! I’m so wasted!” Later, while he sings “Wooly Bully” on stage at the year-end school dance, the camera briefly lingers on his tap-dancing kicks. It’s the most joyful shot in Amy Heckerling’s often emotional film.

“The cameraman knew that I liked feet,” Heckerling once explained to Directors Guild America Quarterly. “I mean, it’s not like I have a fetish, but when you see close-ups of hands or feet, they can be revealing.” The shoes, a photo of which ended up on the soundtrack album’s cover, were Penn’s idea. Said the then-first time director: “Vans should have built him a house.”

Such is the power of Jeff Spicoli. In the past 40 years, there might not be a more influential comedic performance. Penn turned the bleach-blond-haired, smoke-filled-Volkswagen-bus-riding, tasty-wave-catching slacker into an icon of upbeat obliviousness. Now, Spicoli is not just pop culture’s quintessential stoner—his name is synonymous with the word stoner. Nearly every cinematic pothead since the early ’80s is in some way a Spicoli descendent. Slater in Dazed and Confused is a ’70s Spicoli. Floyd in True Romance is a hot Spicoli. The Dude in The Big Lebowski is a boomer Spicoli. And when James Franco was preparing to play Saul, a Jewish Spicoli, in Pineapple Express, he watched Fast Times “about 20 times.”

Spicoli is still the stoner that all fictional stoners are measured by, although his persona may at least be partly based in reality. During the 1979-80 school year, 22-year-old Rolling Stone writer Cameron Crowe went undercover at Clairemont High in Southern California. His experiment as a fake student yielded a book that captured a side of teenage life—complete with sex, drugs, and a strict social hierarchy—that was rarely depicted candidly. Crowe’s semi-fictionalized tale, Fast Times at Ridgemont High, changed names and places and contained composite characters, including a kid called Spicoli. Here’s how Crowe introduced him:

“Jeff Spicoli, a Ridgemont legend since third grade, lounged against the doorframe. His long dirty-blond hair was parted exactly in the middle. He spoke thickly, like molasses pouring from a jar. Most every school morning, Spicoli awoke before dawn, smoked three bowls of marijuana from a small steel bong, put on his wetsuit and surfed before school. He was never at school on Fridays, and on Mondays only when he could handle it. He leaned a little into the room, red eyes glistening. His long hair was still wet, dampening the back of his white peasant shirt.”

Soon after the book’s publication in 1981, Crowe adapted it for the screen, and smartly kept Spicoli in the script. During casting for Fast Times, Penn didn’t appear to be right for Spicoli—or for any role. In his memoir, producer Art Linson wrote that when the actor read his lines, he “flopped around like a beached carp, was barely audible, turned red and said, ‘I don’t really like to read.’” Yet despite the botched audition, Penn somehow convinced everyone that he’d make a great surfer dude. “Defying all logic, all of us in the room quickly agreed he should have the part,” Linson added. “There was something about him! We jumped in blind, and to this day I can’t seem to articulate exactly what it was.”

It was hard for the filmmakers to put what they saw into words, but to them it was clear that Penn had the ability to embody a lifestyle. Once he arrived on set, he was Spicoli. “Sean was clad at all times in full beach ensemble—all conceived and put together by him—including a long, sun-thrashed wig,” Linson wrote. Penn, who in a 2019 interview with Conan O’Brien said that he rooted his portrayal on both material from Crowe’s book and a childhood acquaintance from Malibu, was possibly the first Method stoner. “He didn’t let us call him by his name until the last day,” Crowe, who went on to write and direct Say Anything…, Jerry Maguire, and Almost Famous, told Variety in 2017. “He gave Amy, Art, and I each a ceremonial shoe and said, ‘My name is Sean.’”

Touches of the hazy affect that Penn gave Spicoli has wafted into stoner comedies from Friday to Half Baked to Dude Where’s My Car? But aside from his signature voice and look, what made Spicoli unique was just how much he cared about not caring about anything other than surfing and weed. Judgmental adults and his future? Those were trivial matters. “All I need are some tasty waves, a cool buzz, and I’m fine,” he famously affirms. That line has echoed, in different forms, across countless other movies. In Quentin Tarantino’s Jackie Brown, when Samuel L. Jackson’s gun runner Ordell tells Bridget Fonda’s bikini-clad stoner Melanie that “that shit” is robbing her of her ambition, she replies, “Not if your ambition is to get high and watch TV.”

In Fast Times, Spicoli’s sole ambition is to order a pizza to Mr. Hand’s history class. Ray Walston’s stern, goateed teacher, who’s fond of asking his students whether they’re “on dope,” is the only person who seems interested in challenging Spicoli. By the end of the film, however, it’s clear that even Mr. Hand, like the audience, has a soft spot for Spicoli. When the educator visits his lazy pupil’s home in an attempt to recoup the time that Spicoli cost him during the school year, the two bond.

“Do you have a guy like me every year?” Spicoli asks after Mr. Hand coaxes undivided attention out of him for eight hours of U.S. history lessons. “A guy to, I don’t know, make a show of. Teach other kids lessons and stuff?”

“Well,” Mr. Hand deadpans, “you’ll find out next year.”

Following the release of Fast Times, the Jeff Spicoli–Mr. Hand relationship became the comedic student-teacher archetype. Shades of that dynamic can also be seen in almost any ’80s and ’90s movie where irreverent young people needle authority figures, from The Breakfast Club to Wayne’s World to Election to Lady Bird.

Naturally, not everyone found Spicoli very endearing. There was a backlash among, of all people, surfers. “Just a few months after Fast Times came out, surfing moralists—contest organizers, mostly—began to say that Spicoli was setting a terrible example,” surfer and journalist Matt Warshaw wrote in 2016, “that he was polluting the surf-world waters that they were working so hard to purify.” In 1983, National Scholastic Surfing Association president Ian Cairns, a legendary surfer himself, even told Surfer magazine that in his sport, “You can no longer get away with long hair, cussing, or bad behavior.”

The constant comparisons to Spicoli also occasionally irked those who were attempting to, well, do their own thing. “Bill and Ted are not surfer dudes. They’re not part of that culture,” Alex Winter told the Times before the release of Bill & Ted’s Bogus Journey in 1991. “Spicoli’s comedy was drawn from the hazy cloud that he lives in, the fact that you’re looking at a human being who is only about 15 percent aware of what he’s doing from moment to moment. Bill and Ted’s comedy comes from very different things. They’re much more physical comedians; they’re clowns.”

In truth, Spicoli endures because there was something blissfully aspirational about his lack of awareness. Unlike many teenagers, he clearly felt good about himself and his prospects—even if others were skeptical of them. In Fast Times, he almost exists outside a narrative that features a handful of painful true-to-life plotlines. “I love Spicoli,” Heckerling told Interview magazine in 2016. “That optimism fascinated me.”

More than the bong or the boards, it’s that trait—the bewildering yet admirable ability to happily exist in this world—that’s bled into our pop cultural consciousness. A decade later, when Heckerling was trying to come up with the protagonist of what would become her second classic teen comedy, she looked back on her Vans-wearing stoner. “Imagine going around the world: everybody thinks you stink and you think you’re great,” Heckerling added. “How wonderful is that? Who says you have to think what other people are thinking? Why not wear rose-colored glasses?”

Cher Horowitz may not smoke weed in Clueless, but in her own Beverly Hillsian way, she’s another Jeff Spicoli.