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Matt Charlton creates analogue ash in his digital urn, turning 1,000 CDs into mp3s. Here’s why he’ll never go back.

Jon Boudreau is usually a warm and outgoing guy. Every time I visit the CDPlus location he manages on Barrington we talk for a while about new albums we like and local bands we hate. That all changed a few weeks ago.

As I brought box after brimming box into his store, containing all the CDs I had collected over the past 13 years, I noticed something in his eye: It was the same disappointed look a striking union worker would give a scab as they crossed the picket line. Ian Fraser, also an employee of the store and one of my oldest friends, casually made conversation with co-worker Shawn Duggan to dull the tone in the room. Still, I hung my head in shame as Jon quietly walked out of the store to go to lunch without saying a word.

To back up a bit, I recently sold off my entire CD collection. About 1,000 discs. For the majority of the time I had it, I was a maniacal collector. Not so much the heartwarmingly helpless collector portrayed in High Fidelity, but the more seedy and depressing one of Alan Zweig's Vinyl.

In the past little while, things just seemed different. The Stalin-esque regime of organization I'd upheld in the past began to fail, with CDs spread between a stack in my bedroom, a heap by my computer and random titles at various friend's houses. While I used to get lost staring at the racks holding my collection, now I could barely look in their direction.

Then, one night, I was reading the chapter in Our Band Could Be Your Life on The Replacements. I had been a big Tim fan for a while, but had never got around to the group's other releases. As Michael Azerrad described the album's ragged brilliance, I grew more and more interested in hearing it, until the idea finally hit me—the iTunes Music Store. At first the idea felt similar to the urge to read your girlfriend's diary or visit a pornography site—something that you're just not sure you're 100 percent comfortable with the content of. The more I thought about it though, the more it made sense.

I slowly made my way upstairs, closed the curtains and turned on my monitor. Two minutes later the opening chords of "I Will Dare" were blasting out of my speakers and my plan to sell my CDs had solidified.

During the next few months, most of my spare time was taken up sitting at my computer feeding disc after disc into the hard drive. From Flaming Lips to Drive Like Jehu, from Os Mutantes to Freestyle Fellowship, I loaded them up without remorse, until one came up in the stack—the Beastie Boys' classic Ill Communication. It was the first CD I ever bought.

I spent a few minutes thumbing through the booklet I'd stared at so intently as a 14-year-old. From the bizarre cover to Grand Royal's logo, the whole thing had seemed to hold so much mystique when I bought it from Costco in 1994. Could digital music ever offer the same thing?

I thought about the albums I'd bought online since making my decision. Did they seem less substantial because I could never hold them in my hand? I realized that you can talk about the long tail theory or the death of the CD all you want, the fact is I don't listen to CDs anymore. Maybe digital files don't hold the same aura as an actual unit, but that doesn't make much difference under two years of dust.

The next week I organized a party for some of my friends to come over and look through my collection before I dropped them off at CDPlus. One by one they showed up and picked through them with a frenzied energy I recognized well. It was a similar feeling to watching your ex-girlfriend get hit on for the first time since you broke up with her. Afterwards, I brought the remaining titles down to meet Jon's accusing stare.

A few weeks later, Jon and I bumped into each other at a bar. Walking up to me with a smile he said, "I just wanted to let you know that your CDs are spread out all over the city now." It was the first time the finality of what I had done kicked in, but it didn't trigger any Michael Bluth-esque moments of "I've made a terrible mistake." Just the happy realization that I could still go home and listen to any of them. And that I'll always have my vinyl collection.

The next day I went down to CDPlus and talked to Jon about new albums we like and local bands we hate.

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