From its pure adolescent form on up, cool followed the post-1960s fragmentation of popular culture in general, and mere decades after its invention it became possible to be cool in dozens of different microcosmic forms. So while the counterculture hipster was looking down on the Gatorade track star with disdain, he was desperately seeking to be cool within the narrower confines of his own particular subculture. And suddenly everyone, knives to throats within their miniature culture wars, became a common minion under the umbrella reign of "cool."

And yet, somehow — and this is what makes cool so transcendently pervasive — the collective of cool people from so many private worlds retained some kind of unmistakable common scent, detectable even to underlings outside of the subcultures, and by this sinewy connection came to recognize one another, and so the Good Old Boys clubs of yesteryear with their suits and cigars were made to give way to a New Guard, a ragtag collective of winners, back-talkers, übergeeks and snappy dressers. And the masses embraced the New Guard, because they at least appeared to be accessible and transparent, and they seemed to invite the rest of us along with them: "Come, I'll take you to the real party."

So high school remains the training ground for all of us, and the decade after becomes a bizarre enlightenment during which we discover that the way everyone was in high school is more or less the way they will stay for their whole life — ourselves included. In the cars and coffee shops of adulthood there are more obfuscating elements, plaques and suits and Blue Label whisky, but watch how anyone behaves in a bar, or how he talks about what he loves most, and the unmistakable odor of his (or her) innate coolness wafts readily about him, and the protocol that follows is exactly the same as in the high school cafeteria. The cool people are invited into the back room, and the rest of us are asked if anyone is using that chair.

So, rather harshly, I observe that perhaps the real reason for the fiscal train wreck that Cutthroat Island became is simply who Geena Davis is — and probably, by extension, who her husband-cum-director Renny Harlin is as well. Davis dresses the part, has some good one-liners, and kicks a lot of scallywag ass. She's attractive enough, in a sister-in-law kind of way, and she's as three-dimensional as any blockbuster hero of the same era (which is to say not at all, but that doesn't much matter). But her aura is unmistakably that of the teacher's pet trying to sit at Ferris Bueller's table; she's the good-looking innocent with a little bit of aplomb who got the thumbs-up from the guys when they told her she would play a pirate (once the paragon of cool), not realizing that they were then turning around and chuckling about how silly she would look behind her back.

Johnny Depp, meanwhile, has always been cool. Perhaps the resounding weakness of the largely wonderful Edward Scissorhands is the sense that Depp doesn't quite pull off the gawky ineptitude of the title character; the impression is of a charmer who's in on the joke, wearing the Halloween costume of an outcast. (The character, not ironically, has become a totem of hipster coolness in the years since.) For the role of Jack Sparrow in Curse of the Black Pearl, Depp famously jousted with director Gore Verbinski, in the end successfully lobbying to make Sparrow into one of the most bizzaro characters ever to grace a mainstream studio production. The Sparrow Depp created is a lilting, lollygagging mop of filth, charm, and endless ingenuity, based largely on — who else? — Rolling Stones rocker Keith Richards. He's also deftly magnetic and undeniably cool.

And lo, the first film made more than $300 million through U.S. ticket sales alone.