Some of you are likely too young to remember, but there was a time in the late 80s and 90s when you had to be careful about who you invited to your house. Even the most sane-looking person could have dark impulses, like an overwhelming need to fuck with the CD collections of strangers. If you left them unattended for even a few minutes, you might come back to discover that your music had been unhelpfully re-alphabetized. Or worse, separated by genre or time period, or arranged in aesthetically ornate piles. They were always so pleased with themselves, like they were providing a valuable service. “I noticed that some of your CDs were in the wrong jewel cases,” they’d say. “Daydream Nation was in the case for Doolittle. I mean, how ridiculous is that, right? You never would’ve found it.” The only thing to do was smile tersely, and make a mental note never to let meddling idiots near your music again.

That’s pretty much how I feel about iTunes Match.

It started with that whole iCloud business, which I never trusted or wanted. My wife tried to explain it to me — she was a loyal customer from the beginning — but I smelled a huckster scheme.

“You don’t understand,” she said. “It protects all of your music. You don’t have to worry about crashing and losing everything.”

“Now by everything,” I asked, “you mean just the stuff I bought from iTunes?”

“Well, yeah.”

“That’s like 10% of my music collection. What about the stuff I ripped from CDs? Or the stuff I stole?”

I shouldn’t have mentioned that last part.

“You told me you stopped doing that!” my wife howled at me.

To be fair, I only steal music when it’s absolutely necessary. Like when an artist hasn’t released it yet. Or I can find it online.

“Eric, seriously, you have to cut it out with the online piracy! You have a kid now, don’t do something that’s going to get you in trouble.”

“Oh come on,” I laughed. “You’re being dramatic.”

“You want Charlie telling his friends, ‘Daddy’s in jail because he didn’t want to pay for the new Van Halen record?’”

I would happily stop stealing music, if the Internet made it even slightly less irresistible. It’s like those bookstores that have tables of discounted books (always the shittiest ones) on the sidewalk outside. You’re supposed to come inside and pay for them, but it’d be laughably easy to steal it all with even a modicum of effort. The Internet is like those bookstores, but instead of crappy paperbacks that nobody wants, they’ve filled the streets with every single song in the universe you could possibly ever want. And the employees are all on break indefinitely. It’s not so much a moral question of “Should I steal?” It’s a practical question of “How much of this free shit can I squeeze into my car before the tires blow?”

That’s why I was intrigued enough with iCloud to be frustrated by it. For most of my existence as a music fan, your collection was limited by the available square footage. First, when it was records and CDs, you could own as much music (finances permitting) as you had shelf space. When tangible music was replaced with mp3s, you needed a computer with enough memory to store it all. That may sound ridiculous, especially with the massive number of gigabytes available on most computers. But that memory can get very small very quickly when the Internet starts knocking at your door, like a virtual Dr. Conrad Murray with a medical bag full of goodies. “What do you want, kid? I’ve got everything!”

I was more hopeful about iTunes Match. It’s cheap ($24.99 a year), and it automatically adds all of your music to the iCloud; not just the iTunes purchases but also the stuff that you…. borrowed. And it gets better. According to the Apple website, if you’ve got a song that’s already in the iTunes database, they’ll replace your old, shitty copy with a higher-quality 256kbps AAC file. If they don’t have it, you can upload it. But given that iTunes owns everything even tangentially connected to music, including the skeletal remains of Elvis Presley and Michael Jackson, it’s a pretty good bet that they have whatever you think qualifies as rare. And once they’ve replaced your shabby audio misfits with their pristine, übermensch-quality songs, your entire music catalogue instantly becomes available on “all your Apple gadgets.”

When I first read this exciting news, my first reaction was “Fucking yeah, about time!” But then I got to thinking…

I should tell you, in the spirit of full disclosure, that I own exactly two “Apple gadgets,” an iPod and a MacBook. I adore them both and use them incessantly, but I also enjoy meaningful and satisfying moments in my life that don’t involve even a single Apple gadget. So I was a little confused when the Apple website promised excitedly, like biblical scripture yammering about heaven, that I can now “buy a song from iTunes on your iPad at home, and find it waiting for you on your iPhone during your morning commute. All without having to sync.” Sure, that sounds fine. Or, here’s another idea, I could also go twenty fucking minutes without listening to music. Who the fuck am I, Clive Davis? Since when is listening to music my job? If my smartphone or tablet isn’t loaded to the hilt with every song I’ve ever owned or stolen, that’s not a tragedy. I have the self-reliance and fortitude to wait till I get home.

The other, more important reason why I’m reluctant to hand over my music library to iTunes Match is a bit more complicated. I’m afraid that iTunes, like that guy in the 90s who raided and ruined my CDs, thinks it’s being helpful when actually it’s destroying any sense of individuality and uniqueness my music collection ever had.

I called Glenn, a writing friend from Chicago who knows his way around computers. “So all my old music just disappears?” I asked him, my voice hitting a panicky treble.

“No, no, no,” Glenn assured me. “They just store an identical version in iCloud, but it’s got a better sound quality.”

“What about album art?” I asked.

“All your metadata is transferred to the new audio files. Everything.”

“What if, say, my cover art for Tom Wait’s Swordfishtrombones is the Japanese import with a record store sticker on the front written in Kanji symbols? Will that be transferred too?”

This gave him pause. “Is that important to you?”

It most certainly is.

“And what about genres?” I asked. “Are my files going to revert back to those boring iTunes genres, or do I get to keep my own grouping system?”

I’ve put a lot of effort into coming up with more descriptive genres than iTunes provides. “Alternative & Punk” and “Rock” doesn’t tell me anything meaningful about my music. So I’ve organized my mp3s into categories like “Androgynous Pop-Rock” and “Mildly Annoying Baby Boomers” and “Indie Rock That I’m Marginally Interested In” and “Alt-Country Songs About Booze, Sad Sex and Jesus.”

“I’m pretty sure you could keep that stuff,” Glenn told me, unconvincingly.

“So if iTunes classifies a song as ‘Folk,’ they’ll let me change it to ‘Nasally Musicians I Adore Unconditionally’?”

“I suppose so, sure.”

“And even if they want something to be ‘Blues,’ I can insist on calling it ‘White Guys Playing the Blues That Seemed More Interesting When I Was Smoking Pot in High School’?”

“I really don’t know for sure. Why do you even care about this stuff? As long as the music sounds good, who gives a shit how it’s labeled?”

He’s right, of course. But I give a shit anyway. I’ve spent days — literally 24-hour days — obsessing over this stuff, scouring the Web for the perfect cover art that’s a reproduction of a water damaged vinyl sleeve with the Tower Records price tag still in the upper corner, or trying to decide if the Gaslight Anthem qualifies as “Non-Ironic Working Class Anthems” or “Springsteeny.” If iTunes Match erases all that useless minutiae, then it confirms that it was really just useless minutiae after all.

I still haven’t signed up for iTunes Match. And I probably never will. My music will always be a little flawed. But I like the flaws. I like the hisses and pops of my old CDs, or the hisses and pops of the CDs owned by the people who uploaded them to Pirate Bay. And I like that if somebody picked up my iPod, they’d probably be confused and angry by the asinine way that the songs are organized. I know that I’m living recklessly, the digital music equivalent of bungee jumping. And I’m okay with that. I’m sure there’s plenty of evidence that iTunes has the best intentions and isn’t trying to suck the fun out of my music-listening experience. But I’d rather risk losing it all in a hard drive crash than have my music library become just another homogenized collection of songs. I like my mp3s the way they are, with my initials carved sloppily into the sides.

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