It wasn’t enough for Black Eyed Peas ringleader will.i.am to put out another solo album – particularly after the failure of his last solo outing, 2007’s Songs About Girls, released toward the height of Peas-mania. No, he had to release another LP, and he called it – are you sitting down? – #willpower. That’s right: not only is it a pun, but by turning the title into an automatic Twitter hashtag, will.i.am has ensured that, no matter how popular the record is, it will be remembered first as a product of its time, when the most impressionable pop consumers were verbally referencing popular tech without a care as to how dated they’d sound in a few months or even weeks.

Of course, this sort of desperate attempt to stand on the ragged edge of consumer tech in pop music is nothing new. Even before three of pop’s biggest artists in 2000 used a seismic shift in time measurement for their own gains, musicians were trying to keep up with the hottest equipment on the consumer market, often to embarrassing ends. Here are eight of the most embarrassing or unusual examples of this trend – more than enough to make you nostalgic for a time when it would have made a terrible noise just to get to this page.

The Gap Band, “Beep a Freak” (1982)

“Beep a Freak” may be the most wild example of outdated technology in pop, thanks to the source of outdated entertainment: the beeper. Granted, hip-hop would extol the virtues of two-way paging for much of the late ’90s and early ’00s (even Beyoncé’s “Crazy in Love” makes such a reference), but rarely did they build the entire song around the pager’s chirps and features. What makes “Beep a Freak” even more ridiculous is its chintzy production value, poorly rewriting “You Dropped a Bomb on Me” and punching in silly, pseudo-lewd exhortations like “It’s cheaper to beep her!” Is it, Charlie Wilson? Is it really?

The Power Station, “Communication” (1985)

By this point, reaching a loved one in song across the telephone line was nothing new. But “Pennsylvania 6-5000” and “867-5309/Jenny” were far catchier than The Power Station’s catchall ode to keeping in touch by any means necessary. Even a funky bass-and-drum-laden hook by John Taylor and Tony Thompson can’t offset Robert Palmer’s silly lyrics, which manage to rhyme “cassettes” with “Telex” as if to remind you it’s totally 1985. “Communication,” the third single off this Duran Duran side project’s album, was a relative stiff, only denting the bottom of the Billboard Top 40 where previous singles “Some Like It Hot” and a cover of T. Rex’s “Get It On” were Top 10 smashes.

Squeeze, “853-5937” (1987)

It’s not that writing a song about a phone number is dated. No matter how much the Internet becomes ingrained in our lives, we’ll always have seven digits to turn to when drunk-dialing exes or ordering pizzas. But British pop band Squeeze got a little too cheeky on this cut from 1987’s Babylon and On, turning singer/songwriter/guitarist Glenn Tilbrook’s answering machine message into a full song. In a 2004 biography on Squeeze, Tilbrook said he was “heartily ashamed” of the song, while lyricist Chris Difford damned it as “nonsensical.” Astoundingly, it was a U.S. Top 40 hit, charting higher than the band’s signature song “Tempted.”

Sir Mix-a-Lot, “Beepers” (1989)

Three years before topping the charts with a song about a, shall we say, more timeless subject, Sir Mix-a-Lot released this ridiculous instructional on pager culture as it applied to pimpin’. If the maniacal samples of Skypager menu options and beeps won’t drive you nuts, perhaps the threadbare groove (sampled from Prince’s “Batdance”!) might.

Prince, “My Computer” (1996)

Speaking of Prince, we all know The Artist’s commitment to technological ideas both in his lyrics and on record. (This probably hit its apex with “Computer Blue,” the scintillating album cut from Purple Rain.) More than a decade later, this mid-tempo ballad from sprawling triple-album Emancipation recalls some of the best obscure tracks from the late ’80s (dig that synth orchestra!) and soul-searching lyrics about finding a better life than what the machines have to offer. (There’s also some great background vocal work by Kate Bush to enjoy here, too!) But you’ll be forgiven if you can’t hold it during the track’s bookended exclamations from the infamous America Online voice. You think Prince still hears “You’ve got mail” when he logs into his e-mail?

Britney Spears, “E-Mail My Heart” (1999)

This middling album cut from Spears’ bestselling debut …Baby One More Time is particularly ridiculous thanks to how little the tech angle actually plays into the song. Outside of some lines in the refrain, this is a pretty simple “I-miss-you” ballad – not to mention one of the schlockier selections off the album, thanks to production not from Swedish übergeniuses like Max Martin but a runner by the name of Eric Foster White, who was responsible for the album’s most moderate hit, “From the Bottom of My Broken Heart.” As album tracks go, this one totally belongs in the spam folder.

R. Kelly, TP-2.com (2000)

Really, all Kells had to do was name his fourth solo album 12 Play 2 or something. But this was before the dot-com bubble had yet to burst, and so it just seemed…right to name an album after a website. Or was that the other way around? Fortunately, TP-2.com doesn’t go for gimmicks past its title, instead focusing on solid R&B cuts like “I Wish” and “Fiesta.”

Soulja Boy ‘Tell Em, SouljaBoyTellEm.com (2007) / iSouljaBoyTellEm (2008)

It’s one thing to hook yourself up to a tech trend as it’s popular. It’s another to hook yourself to not one but two tech trends long after they’d entered the normal lexicon. The only thing staler than Soulja Boy’s album titles were his Fisher Price hooks and mushmouthed delivery – neither of which stopped novelty single “Crank That (Soulja Boy)” from topping the Billboard charts for seven weeks and earning a Grammy nomination.

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