Portable audio used to be strictly for joggers and the kids who smoked under the bleachers, but these days everybody and their guidance counselor has an iPod. So how did headphones become fashionable, and MiniDisc devotees get left by the wayside?

As I cling to the greasy subway pole during rush hour, I realize that New York, ever changing, ever developing, has sprung a whole new appendage: white bud earphones. All of the people in my subway car—the man in the pinstriped suit, the stern middle-aged woman, the dreadlocked teen—are zoned out, far away in their private iPod worlds. I wonder: What revolution took place that finally made portable audio so popular, and when did it happen? After all, it wasn’t that long ago that David Sedaris, in his book Me Talk Pretty One Day, ranked the Walkman somewhere between boa constrictors and Planet Hollywood T-shirts in terms of vulgar accessories. And yet the iPod and its sleek, easy-to-use features dragged portable audio out from the shadows of uncool and into the spotlight, blinking.

Traditionally, Walkman users were sullen teens, fitness enthusiasts, and the likes of Otto the bus driver from The Simpsons. I wasn’t any of these things in 1998, when I began college. Giving up my car was my hardest adjustment to college life, for I grew up in the suburbs, where we spent most our time driving to and from places that invariably sucked. Getting high and blasting the stereo on the road was a scarce salvation afforded by that era. All that teenage wasteland must’ve altered my brain, because at college traveling from one point to another suddenly seemed unfathomable without music.

Armed with the memory of my ‘85 Honda and its fully loaded Kenwood system, I made my way past the toasters to the back of the Circuit City, where the portable-audio section lived beneath a row of can lights. Collected here was a forlorn group of DiscMen and cassette players, half of them store returns, their packaging creased and taped shut. They were uniformly plastic and ugly, and very often bright yellow. All were roughly the same price, with the same limited functions: play, stop, fast-forward, and rewind. Behind me, home and car stereos thumped their brazen capabilities, but in the back of the store, I was sole witness to the hottest innovation going—the auto-reverse cassette. A clerk approached.

“I need a Walkman. Desperately,” I whipped around and explained, waving a white and yellow “Sport” Walkman with matching wristband and headphones at him. “But I don’t know if I’m this desperate.”

The clerk flashed a knowing smile and guided me to a kiosk a few feet away, where he revealed Sony’s first MiniDisc recorder/player. It was half the size of a cassette Walkman and came with black headphones that folded up in my palm. No yellow plastic here—the player was made of real metal, which gave it a weight and seriousness that matched my musical appreciation. So I bought the thing for $379.

Visibly, my MiniDisc player followed the formula for “technologically advanced”: small and silver with an LCD screen and several outputs. Similarly, the discs were small, brightly colored, and supposedly indestructible. I could reuse them, which came in handy when my player randomly flashed “error” and erased entire discs. This happened—often.

So what set it apart from cassette and CD players, besides a few hundred dollars? I remember only one MiniDisc commercial—it featured a dude picking up a hot chick in a convertible and charming her with the mix he’d just made on his portable player. The camera closes in on the LCD screen, across which scrolls the title: “My Baby’s Mix.” She’s impressed, they drive off, and the viewer is left in a cloud of exhaust. I’d like to know what happened to the rest of the commercial, such as the suspenseful 10-hour scene where the dude is making the mix, and attempts to simultaneously hit “play” on the CD player and “record” on the MiniDisc, yet fails every single time. Or the hour he spends clicking through the alphabet on the two pinhead-sized buttons to spell out the title—followed by the crushing realization he has just typed “My Boby’s Mix” and must start all over again. But no MiniDisc owner would want to watch that kind of ugliness. Like the commercial, we focused on the miracle of a scrolling song title, the kind of progress no other player could boast.

On my campus of 45,000, only five other geeks had MiniDisc players, and so our friendship arose from necessity—who else could we trade MiniDiscs with? Granted, I needed a machete to hack through the speaker-wire booby-traps and snarled A/V cable to get into their dorm rooms. We MiniDisc-ers wore our special folding headphones like mantles and giddily discussed the player’s possibilities. Already we could record vinyl, our voices, the TV, an answering-machine message, and then walk away, listening to it—what could be next? The MiniDisc future seemed bright and likely to involve holograms and organic computer chips. Sure, it was painstaking at times, but when people asked us about our “high-tech Walkman,” we could proclaim the myriad reasons why MiniDiscs were The Wave of the Future.

Us: Look at the title scrolling. Pretty cool, huh?

Them: But a MiniDisc can’t hold more than one CD? Then what’s the point?

Us: Three words for you: In De Structable.

Them: And you can’t record faster than real time?

Us: See how this MiniDisc fits in the palm of my hand?

Them: Seems like there’s some sound quality lost going from CD to MiniDisc.

Us: Listen, do you want to hear this mix of Emma’s drunk answering-machine message dubbed over the Pet Shop Boys, or not?

I snorted off the skeptics and traced my finger along the LCD screen, knowing in the pit of my stomach that the wave of the future was going to need more than six people. At night, erased discs and mistyped titles like “Dork Side of the Moon” and “Are Lou Experienced?” haunted me. Within a year of its purchase, my player crapped out, becoming the third one to go in our group. With a forced smile, I bought a new model, this one made of plastic. Months passed and the MiniDisc crew explored more mainstream avenues, such as downloading mp3s, which proved to be the real future. I held on until the third player, then threw it against a wall when it died.

So when the iPod first appeared, I was wary. Like when meeting someone new after a bad breakup, I wondered if this player would deliver on its promises, provide for me where the MiniDisc had failed. Like everyone else on the planet, however, I eventually bought one and am now obsessed with it, though sometimes I think the iPod is almost too easy. Take that scroll wheel, for example. A bit of resistance would be nice. It drives me crazy how many times I blast past the “the Smiths,” hitting everything from “XTC” to “Smashing Pumpkins” before finally selecting it. And 40 gigs of my music library at my fingertips makes it hard to decide what to listen to.

It’s these small difficulties that make me think fondly of the MiniDisc days. People later called us suckers, but my MiniDisc crew had a vision of a world where portable audio and dignity weren’t mutually exclusive, a vision that to us looked very much like a New York subway where dozens of riders enjoy whatever is pulsing through their tiny white wires. I hear MiniDiscs are still going strong in Hong Kong and Japan, but in the U.S. they are marching to wherever the BetaMax went. Today, a hundred MiniDiscs sit in a shoebox in my closet. They contain priceless music archived for eternity, and until I move to Hong Kong, I will continue to lug them through each phase of my life in the off-chance that I meet a kindred soul with a player that still works. Because there’s a killer Pet Shop Boys song with me screaming for pizza on top that I’m sure they’d want to hear.