The magic of your old iTunes library

A few weeks ago, my wife and I were looking for a specific Iron & Wine song. Actually, we were looking for a live recording of a specific Iron & Wine song. Actually, we were looking for a specific live recording of a specific Iron & Wine song.

And we couldn’t find it. Definitely not on Spotify, and not even in the depths of YouTube shaky phone recordings. We found other studio and live recordings of the specific song, but not the one we wanted. This one was different. It was special. It was beautiful. And none of the other versions quite captured the magic.

It was as if it didn’t exist. But it did. We both remembered it, and even college friends we texted remembered it.

And this is when I realized something: As amazing as it is to have a vast library of music in my pocket at all times thanks to Spotify, there’s a magic to the curated music libraries we built in the Before Times that it can never match.

I obsessed over my iTunes library in college. There were no “Unknown Aritst” listings in my library. Every file was meticulously categorized, named and organized. Even the ones that were possibly/maybe collected in a not-quite-above-board way, I went into each file and added the necessary metadata. (Oh, to have that kind of free time again.)

I curated playlists for parties. I thoughtfully burned CDs for friends. (In the peak of my college hubris, I burned one called “If Jesus Had a Stereo” and gave it to my new girlfriend at the time — and she still married me. I recently found that CD, and it’s a wild ride through 19 songs.)

When Spotify came along, I forgot all about that iTunes library. I thought I had everything I needed right there in the app. Any song that I had on my iPod classic I could find on streaming. Or so I thought. Until I went looking for that specific live recording of that specific Iron & Wine song.

That’s when I realized the magic of those locally stored libraries. Of having music that you own, that’s yours. Music that Spotify or a record label can’t take away. (There’s one song on “If Jesus Had a Stereo” that just doesn’t exist on Spotify, even though the band who created it has a verified page on there. I guess they just decided this album — which I loved — didn’t need to be on streaming.)

Sure, I still have my CD collection and a rack of vinyl, but those pale in comparison to the gigabytes of music I had on my iTunes library.

The computer I had right out of college doesn’t work anymore. The kids use it as a toy. And the hard drive I used to back up my music died years ago. My iPod Classic was stolen out of my car as well. So I thought this music was gone forever.

But earlier this week, in a last-ditch effort to find that specific live recording of that specific Iron & Wine song, I pulled out my wife’s old external hard drive. I dug through layer after layer of folders, realized I had, at some point, backed up my iTunes library on her drive … and there it was. The specific live recording of the specific Iron & Wine song, exactly as we remembered it. And it was beautiful.

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So I went down a rabbit hole. How can I make sure I can always access those very specific songs that don’t exist anywhere else?

Now I’m creating a Plex server and figuring out how to get an always-on computer hooked into my router so I can stream that specific live recording of that specific Iron & Wine song whenever I want.

If I ever get it successfully set up, won’t you please remember me … happily.