“What you have here,” Karl the Apple store employee tells me, “is an iPod classic.”

I cringe a little, because the word “classic” always makes me cringe. Unless you’re talking about soda, “classic” hardly ever means “better.” It’s usually a polite way of saying “old.” I’ve reached an age when most of the things I love are becoming “classic” at an alarming rate. This is especially true when it comes to music. A good 85% of my music collection has or is on the verge of crossing over into classic rock territory. I’ve only recently (and still begrudgingly) accepted that U2‘s Joshua Tree is considered classic rock now. And despite having heard it categorized as “classic” repeatedly, I refuse to admit that Neutral Milk Hotel’s In the Aeroplane Over the Sea shares any DNA with music created by old hippies with comb-overs and grandchildren. But okay fine, I’m a realist, I know that time marches on, and when 15 or more years have passed, it’s unrealistic to think that the things that seemed so fresh and current yesterday aren’t showing a little rust today.

walkman

But not in this case. Not with a music-playing device that I bought shortly after a black man was elected U.S. president. Just by the numbers, that’s not nearly enough time to give anything nostalgic street cred. “Oh remember when Mad Men was kinda new and we were fighting two wars in the Middle East and Katy Perry was still married to Russell Brand and my iPod wasn’t considered embarrassingly old?”

I never would’ve known that my iPod was a “classic” if I hadn’t brought it into the Apple store because of a cracked LCD screen. And I probably wouldn’t have thought twice about my iPod’s less-than-perfect LCD screen if it wasn’t for those goddamn kids and their judgmental sneers.

I’d be the first to admit that my iPod isn’t the prettiest girl at the prom. It’s been dropped and scratched and kicked and abused in a myriad of ways. But it’s also been loved, and loved hard. Which is why it hurts when people in their 20s stare at it like it’s a pug in an E-collar.

“Good god,” the checkout girl at the grocery store says when she catches a glimpse of my iPod. “How old is that thing?”

I’ve been walking around with portable music devices for roughly the last 30 years of my life, and only recently have I heard this question. I have no clue how to respond. Is it a rhetorical question, or are they earnestly curious about my warranty?

“It looks like Gordon Gekko’s cellphone in Wall Street,” the barista at the coffee shop down the street from my apartment remarks, covering her mouth to muffle her laughter.

“You think so?” I’ll ask, holding up my iPod so she can take a better look, as if her observation is somehow meant as a compliment.

“It’s so big,” the receptionist at the doctor’s office says.

“If you think my iPod’s big, you should see my prostate,” I’ve retorted. But not out loud. In my head. Long after the moment has passed, and I’m miles away, rocking out to my “Bitchin’ 90s Alt-Rock” playlist.

Sorry. “Bitchin’ 90s Classic Rock.”

“You should think about getting an iPod Touch,” Karl the Apple Store employee tells me. “It’s got a lot more to offer.”

“Like what?” I ask. Which is all the excuse he needs to talk to me for the next 20 minutes about nothing I care about or understand.

I won’t bore you with the details. Because I can’t think of a way to recount the details without sounding like a very old man with his pants pulled up to his nipples. Let me just say this; I own several hip-hop albums (I call it “hip-hop,” I want it noted for the record, not “rap”), and I have not once in my adult life complained about how modern music is too loud or confusing or stupid. But that said, I don’t think any music-playing device, no matter how advanced, needs to be capable of recording video in high definition. I really don’t. I’ll go out on a limb here and say that any definition of video on a music-playing device is unnecessary. High definition, low definition, blurry definition. I’m fine with just the music. Really. If I’m listening to, say, the new Sleigh Bells album, and mid-”Comeback Kid” I’m incapable of making a stop-motion animation video based on my complex emotions inspired by the song, I’m pretty sure I’ll be okay.

Karl the Apple store employee is kind enough to tell me about the 200 or so new software features available on the iPad touch, among them something called a “shake shuffle,” resplendent album art, and apps up the wazoo. I don’t know why I need any of this, as I was already pretty satisfied with my original iPod, despite being a “fifth generation,” which I guess I should be embarrassed about. Karl says “fifth generation” in a hushed tone, like it’s something I wouldn’t want my parents finding out, the equivalent of telling them that I live in a garden apartment with three other guys and I spend my days masturbating to magazine porn purchased at a nearby gas station. (Because nothing shames a parent like knowing their son masturbates like a lonely guy from two decades ago, i.e. “classic” masturbation.)

“How many songs can this thing hold?” I ask. Because in the 21st century, it’s the only reasonable question to ask about an MP3 player. It’s like getting a ticket on a moon shuttle and asking anything other than “Does this thing have enough oxygen to keep me alive?” All the rest of it, all the technical mumbo-jumbo, I’m going to assume the shuttle people know what they’re doing and I’m getting the best that science has to offer. Just tell me I’m not going to die.

“Well, the 64 gigabyte iPod Touch can hold around 14,000 songs,” Karl tells me.

This does not sound like a lot. And because the iPod Touch costs $400, it also sounds like a fucking rip off. I paid that much in 2008 for a “classic,” and that little bastard could squeeze 40,000 songs into its (apparently morbidly obese by 2012 standards) frame. Now granted, I’ve only filled it with (at press time) 7891 songs, and that’s including all the shit I don’t even listen to, which means I have a 32,109 song leeway. In clothing terms, I’m a toddler in size 44 pants. I will never be able to eat enough burritos to fit into my iPod pants. But I like knowing it’s there. The extra bagginess gives me peace of mind.

Karl takes me through the store, introducing me to a dizzying array of Touches, Nanos, Minis and Shuffles. An Apple store is like a Taco Bell; everything looks different, but it’s all just slight variations on cheese and white flour. Apple has apparently spent the last five years trying to fix what isn’t broken. The moment they created a hand-held instrument capable of playing EVERY SONG YOU COULD EVER WANT OR NEED TO HEAR FOR THE REST OF YOUR LIFE, they were essentially done. Anything more than that is just greedy, and it misses the point. It’s like saying, “Hey, I discovered a cure for cancer! Also, it can take some really amazing family photos and the Internet connectivity is stellar.” You don’t say? Well that’s great, but you kind of had us at the “cancer cure” part.

Karl tries to sell me on an 8 gigabyte iPod Touch. It holds a mere 2000 songs — a laughably small number — and it’s just a fourth generation, which may become obsolete, Karl tells me off the record, when they release the fifth generation sometime this year. But it comes in white, which has only been available since October! Can you imagine such a thing? White iPods!

“So what you’re telling me,” I ask, “is that for the same price I paid for a Sony Walkman back in 1980, which lasted for thirty years and could play a limitless amount of music, I can have a white MP3 player capable of holding Bob Dylan’s discography, which I’ll probably have to replace in a few months?”

Karl smiles. You can see it in his eyes, he can’t wait to talk about me to the other blueshirt nerds back in the break-room. “I think you’ll find that the sound quality on an iPod Touch is a little superior to a Walkman,” he says.

Challenge accepted.

I still have my Sony WM-DD9. It’s been in my closet since 1998, when I finally gave up cassettes for good. I don’t know why I still have it. My closet is also filled with every computer I’ve ever owned, but that’s because I haven’t figured out how to erase all the porn, and I don’t want the guys at the dump to dig around my hard drive(s) and think, “Holy lord, this guy was into some sick shit.” But my Walkman has no evidence of past musical misdeeds, other than the Counting Crowes cassette that’s still in there. I guess I always knew, somewhere in the back of my mind, that I’d come running back to it again someday.

The sound is shockingly good. Not iPod eighth generation “now available in silver, turquoise blue, or off-applesauce” good, but “I’m going to take a walk and listen to some tunes” good. It’s noticeably heavy, which I like. The iPod Touch weighs four ounces, and the Walkman is a meaty twelve ounces. It’s the difference between carrying around a credit card and a hoagie. The Walkman’s gears make a high-pitched grinding sound, and the whole thing is held together with electrical tape and Soul Coughing stickers, but otherwise it’s in perfect working condition. Are there special features? You’re fucking right there are. You’ve got your volume control and your gold-plated headphone jack and your auto-motherfucking-reverse. That’s right, bitch, I ain’t flipping my tape manually. I let technology do it for me. Oh, are you familiar with something called “Mega Bass?” Flick that shit from “norm” to “max” and get ready to melt your brain.

But here’s the really strange part. Those smirky kids, the ones with the birth certificates from the 90s who were so perplexed and bemused by my iPod “classic,” are downright mesmerized by my Walkman. I’m no longer the old dinosaur who can’t keep up with the changing times. I’m the crazy old dude carrying around an RCA gramophone with the big cone speaker, humming along to his favorite Jelly Roll Morton records.

“Does it work?” the checkout girl at the grocery store asks, touching my Walkman gingerly like she thinks it might disintegrate.

“It works fine.” I point towards the cracked screen, where the tiny wheels are turning loudly, grumbling in protest. She stares at it, unblinking, like she’s never seen anything so weird and magnificent.

(This story originally appeared, in a slightly different form, on MTVHive.com.)