Pop culture obsessives writing for the pop culture obsessed.
Pop culture obsessives writing for the pop culture obsessed.
Sean Penn, Jimmy Fallon
Sean Penn, Jimmy Fallon
Screenshot: The Tonight Show

In a pre-Lebowski world, Fast Times At Ridgemont High’s Jeff Spicoli was the cinematic standard for the California holy fool stoner. Buoyed by privilege and billowing van-fuls of weed, the quintessential surfer dude rankled martinet teachers like Ray Walston’s Mr. Hand simply by living on a planet where the rules are all to be questioned, not so much out of bratty rebelliousness, but because things just look different from there. And while Jeff Bridges is categorically not The Dude in real life, there’s a certain Zen (and stoned) amiability to Bridges whole vibe that made his casting in the Coen Brothers’ sun-dappled L.A. noir doodle cosmically inevitable. Sean Penn, on the other hand, is not the first actor who comes to anyone’s mind when casting the “good-natured, blissful guy.”

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Appearing via internet on Wednesday’s Tonight Show, Penn—chain smoking (cigarettes) as is his way—took time away from somberly and earnestly telling host Jimmy Fallon about the undeniably good and necessary charity work he’s doing these days to talk some old school Hollywood. (The actor-philanthropist has deployed teams to do free COVID-19 testing across the country, including for Black Lives Matter protesters.) And while it might be hard to square the long-ago (Jesus, nearly 40 years long-ago) quintessential laid-back stoner Jeff Spicoli Sean Penn with the infamously intense, notoriously prickly, decidedly problematic, serious-minded Penn of today, surely the early-20s Sean Penn was a lot looser, right?

“I felt—long before I had a penny in my pocket—that I had had a kind of feeling of entitlement as an actor,” Penn reminisced about his disastrous first audition for Fast Times director Amy Heckerling. Now, wait a minute, judgmental types, Penn only means, “Not because I thought I was so good, but because I thought that the rest were not so good.” Oh, well, that’s not that much better. Regardless, Penn favored Fallon with his memories of almost blowing his big break, explaining that his initial unwillingness to audition for the part stemmed from his conviction that the part was his by right, and that his inner complaint, “Don’t they know what’s going on inside me?” should have clued casting people in to that fact. Penn chuckled about his youthful bullheadedness, sure, but did so in a way that suggests that, yeah, they really should have just given him the part on the spot.

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Still, Jeff Spicoli continues to bring some good into this world, as Penn has organized an all-star table read of the original, Cameron Crowe-penned Fast Times screenplay to raise funds for the worthwhile work of his charity, CORE. (Penn’s involved, but he’s not playing Spicoli this time, and he’s not telling what famous friends are filling out the cast.) And, just to stick with the concept of guys you don’t really think you’d want to hang out with but who are doing some genuinely good things, the whole thing was comedian Dane Cook’s idea, with the oft-maligned stand-up and actor putting up what sounds like a sizable donation to get things rolling.

Contributor, The A.V. Club. Danny Peary's Cult Movies books are mostly to blame.

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