I’m ringing out the old year by doing a massive overhaul of my iPod’s contents. For Christmas my best friend gave me a 500 GB external hard drive that contained all the music in his collection, plus thousands of songs from two other friends. I have no idea how many songs there are in all, but it certainly numbers in the thousands. It’s like finding an entire record store—a quirky one—tucked away under the tree.

I’ve spent the last few days trolling through the files trying to figure out what I need to add first. The hard drive includes tons of stuff that I have on vinyl and cassette but not in digital format, so I added things from the Swimming Pool Qs, the Housemartins, XTC’s Skylarking and a slew of songs from the great cowpunk band Rank & File. One library contains dozens and dozens of TV theme songs, so I put on “The Rockford Files” (I had purchased the single when it came out) and a version of the glorious and glamorous theme from The Avengers. There’s stuff I’ve always wanted but never owned, including The Modern Lovers. There aren’t many songs that can get me pumped the way “Roadrunner” does. I’ve found tons of individual songs that I’ve always liked but never owned, including “Do You Want to Hold Me” by Bow Wow Wow and “Digging Your Scene” by the Blow Monkeys. The only digital version of Frank Zappa’s “Montana” that I had was the single version, which ditches the guitar solo (!).I finally have the song in all its string-bending glory.

And I’ve barely scratched the surface.

Of course, adding new songs to the iPod means ditching some old stuff. I feel bad whenever I purge something from the iPod. It’s like laying off a loyal employee. How can I diss Stevie Wonder by dumping Innervisions and Songs in the Key of Life? Well, I made up for it a little bit by adding Talking Book. A friend had loaned me his copy of Nick Lowe’s two-disc Quiet Please and I had loaded all 40+ songs on the iPod, but now it’s time for someone else to use those megabytes. In this case some are now eaten up by some songs that Lowe produced for his then-wife Carlene Carter, and some more to the Brian Eno/John Cale collaboration, Wrong Way Up, an album I previously had only on a cassette buried in a box in my furnace room. Oingo Boingo’s Nothing to Fear stepped aside to make room for Danny Elfman’s So Lo. Just to make sure I don’t get hopelessly mired in nostalgia, I also threw on some Arctic Monkeys. I’ve heard very little of their music, but I get the sense you have to know them if you want to claim any shred of hipness. Or maybe that was three years ago. At my age I’ll take whatever hipness I can stumble across.

I added Pictures on a String by a band called the Comateens. They were a trio—two guys (brothers) and a girl—and I interviewed them for the little rock magazine I edited in Boston. That must have been around 1984 and I really enjoyed their quirky dance rock. The next night the band was playing at Bates College in Maine and they told me they didn’t know anyone up there, so I could add as many people to the guest list as I could find. I put the call out to family and friends in Maine and I drove up with Fred, a guy I knew from high school who was living near Boston at the time. We all had a great time, and my contributions to the guest list made up a disappointingly large percentage of the audience. Well, the losers at Bates didn’t know what they missed. I fell asleep on the drive back, with my knees jammed up against Fred’s glove compartment. That’s where he kept his tape deck but rather than wake me up, he listened to the same tape all the way home. That struck me as a truly selfless act. (It also reminds me of a Steven Wright joke, in which he told how he once drove across the country with only a single tape to listen to. “I can’t remember what it was,” he said.)

I also added a great Isley Brothers collection. I have a “best of” collection on vinyl, but nothing iPod-capable. Now I do. I’ve always loved “That Lady” and its soaring guitar solos. To me it’s the quintessence of the 1970s. I particularly recall one early morning when I was in the car with my father and my brother on the way to go duck hunting. It was cold outside, it was brutally early, but the car was warm and I was half asleep in the back seat as we headed through the darkness down to the coast, tires humming hypnotically on the blacktop. On the radio, fading in and out of the static like something from a fever dream, I heard “That Lady.” I think of that every time I hear that song.

That was a long time ago—back when we lived in an analog world. Times sure have changed.

Happy Digital New Year!