4. Bow Wow Wow, “C30, C60, C90, Go!” (1980)
“Home Taping Is Killing Music,” went the record industry’s panicked cry during the mid-’80s; this 1980 song from Malcolm McLaren’s second-most-controversial act (after the Sex Pistols) could have been the cause for alarm. “My cassette’s just like a bazooka,” shouts teenager Annabella Lwin over pseudo-African drumming and giddy guitar chords. “I don’t buy records in your shop / I tape them all off Top Of The Pops.” The industry wanted to impose a hefty levy on blank tapes to make up for perceived losses in income; consumers responded by purchasing more pre-recorded tapes than vinyl LPs—until the CD came along later in the decade. Then, of course, file-sharing opened the floodgates, and cassettes—and songs like this—became signifiers of a more innocent past.
6. Brittney Cleary, “I.M. Me” (2001)
While instant messaging is still en vogue—whether it be through Facebook, Gmail, iChat, or whatever—something about Brittney Cleary’s “I.M. Me” is already incredibly out of touch even a mere nine years after its release. From the creaky door opening and trademark America Online “Hello!” at the kickoff to 12-year-old Cleary’s creepy, Shania Twain-like, adult-lady voice, this Radio Disney hit is orchestrated to the nth degree to capitalize on some focus-grouped idea of what “these kids today” are into. As such, “I.M. Me” is riddled with TTYLs, BBFNs, and pleas to “sign my guestbook with your screen name,” so it’s ever-so-poignant when Cleary wails, “It’s easier to type than use a pen.” Too true, Britters. Too true.
19. Bruce Springsteen, “57 Channels And Nothin’ On” (1992)
The Boss lost his way creatively in the early ’90s when he pulled up stakes in New Jersey, ditched the E Street Band, and moved to Los Angeles to work with hotshot studio musicians on what turned out to be his two least-regarded albums, Human Touch and Lucky Town. Even Springsteen seemed to realize this—as it was happening, no less—judging from the Human Touch highlight “57 Channels (And Nothin’ On),” which uses cable TV as a metaphor for the emptiness of his newfound Hollywood lifestyle. The only problem is that, in retrospect, having a cable package with only 57 channels hardly seems luxurious enough for a man who “bought a bourgeois house in the Hollywood hills with a truckload of hundred-thousand-dollar bills.” It certainly doesn’t seem like enough options to spend switching “‘round and ’round ’til half past dawn.” These days, everybody knows you can whip through 57 channels in less than five minutes, which is about as long as it would take for a rock star like Springsteen to get back on the phone to rustle up a better cable provider.
20. Prince, “My Computer” (1996)
Naturally, Prince—who’s always been fascinated by technology—was a fairly early adopter of the Internet. “My Computer,” from 1996’s triple-CD Emancipation, beats out the same album’s “Emale” (which is more of a traditional boy-meets-girl song with some cyberspace attached) as a wide-eyed harbinger of “a better world, a better life” to come through technology, complete with friendly America Online samples of “Welcome!” and “You’ve got mail!” “I scan my computer, looking for a site / Somebody to talk to, funny and bright,” he sings on the chorus. Clearly, nobody could have told him about the “firsties” cesspool that message boards and comment-boxes would devolve into. Perhaps that’s why he recently declared the Internet “over,” thereby rendering his own song obsolete?
25. Paul Simon, “Kodachrome”
A breezy examination of the fallibility of memory, Paul Simon’s song pits reality against the souped-up colors of Kodak’s flagship film stock. Photographs, he sings, “make you think all the world’s a sunny day.” By way of an example, he convenes an imaginary summit of his ex-girlfriends—the ones, presumably, to whom his thoughts drift when his current relationship starts feeling oppressive—then cops to the fact that they probably weren’t so great, either: “Everything looks worse in black and white.” As of 2009, Kodachrome is itself merely a memory, a relic of the era before digital cameras and hi-res cell phones. Nowadays, we’re drowning in images, whose capture often supplants the experience they purport to document. Simon’s song now evokes nostalgia for a time when pictures came in finite rolls, and you could go to a concert without having your view of the stage blocked by a wall of iPhones.
Update: When I first posted this, I accidentally deleted the original link, from AV Club.