What the iTunes taught me: a broken man's plea

It's the Divil. The Divil, I say!

I haven't been blogging as much lately, because I've been holding down a part-time job converting my CDs into digital files on iTunes.

The job pays nothing and is among the most boring, lonely, and frustrating experiences available to humankind on planet Earth. By the end of the experience, you don't just hate your music collection, you hate all music.

I converted my CDs into digital files once before, when iPods first appeared on the scene all those years ago - er, 2001. Barry Bonds was the home run king, Tom and Nicole broke up, Creed rocked the Billboard charts, and there was some bin-Laden thingamajig in New York or something.

I remember thinking that my iPod looked pretty futuristic and cool when I first took it to the gym. I'd been using a portable CD player, which skipped when I skipped and stopped running when I ran. It also weighed about 400 pounds, so the iPod seemed like a godsend in comparison.

And, like some of the best and most-successful products around, that first iPod contained a lot of mystery. Forget the Caramilk secret, the "what's in the iPod" question had me and my friends guessing for years.

For instance, why, when I put it on shuffle mode, would I get the Clash's "Police on my Back" right after the Police's "King of Pain?" It was like the iPod was daring me to look for connections in the music. "You're right, iPod! I do like songs by the Police or with the word "police" in them!"

Eight years later, when I look at that original iPod, I think, "What a clunky piece of junk." It not only doesn't play video or respond to my touch, but the screen constantly freezes, making it no function and all form: what I now have is not an iPod, but an expensive doorstop that looks like WALL-E's ladyfriend.

I've also lost my iPod innocence - sometimes The Monkees' "Daydream Believer" comes up after the New York Dolls' "Dance Like a Monkey," but I chalk it up to random coincidence rather than conspiracy. You gotta let some things slide...

Less is more is less, more or less

When I converted my CDs the first time, I took a "more is more" approach. I took every CD I owned at the time, and transferred each over in its entirety. I've always been more of a guy who likes albums over singles, and - at thousands and thousands of songs - I figured that I was good to go forever.

The problem: when you're at the gym, you want upbeat, lively music that energizes you; the Smiths may be perfect for a 2 a.m "poor me" session, but they're not so great for the rowing machine at 4 p.m. Although "Heaven Knows I'm Miserable Now" does summarize my workout thoughts quite concisely.

As a recent iPhone owner, which I use for everything but phone calls, I figured I'd convert my CDs again, but this time have some method to my madness.

"What if," I wondered, "I condensed the playlist to my favorite 1,000 songs of all time?"

No longer would I guiltily skip over Brian Eno's "Music For Airports" on the treadmill; instead, I would do what the Ramones first set out to do with their songs, as described in the Spin Alternative Record Guide:

"What if you took only the giddiest peaks of your favorite songs, the second verse, which is the same as the first, in Herman's Hermits' "I'm Henry VIII, I Am," or the roller coaster screams in "Palisades Park" - and played them over and over? And what if you left everything else to Traffic fans to bother with?"

This flies in the face of most people's "more is more" philosophy that music's conversion to the intangible has created: no longer is there snob appeal in what you're listening to, because everyone has the same portable listening device. Instead, it's all about how many songs you've got on your iPod, iPhone, or iTunes.

I'd been down that road before. This time, it would be only the hits and the favorites. Simple.

Quality vs. quantity

Not really.

Part of the problem is the sheer number of CDs I have in my collection; I could easily construct a fortress of solitude out of them, and never interact with another human being again. Hey, sounds like a plan!

After I transferred over "just my favorites," which took me two weeks, my iTunes library sat at over 5,000 songs. So, I started the editing process. First, I considered which songs I'd want to have on me "at all times" - the desert island approach.

I consulted Rolling Stone's 500 greatest songs of all time to help me figure out which ones are truly essential. A funny thing happened: I started adding, not subtracting songs:

"Yeah, I should have Led Zeppelin's "Black Dog" in there, and Outkast's "Hey Ya!," and Simon and Garfunkel's "Bridge Over Troubled Water..."

In a complete breakdown, I added five Sam Cooke songs. And, I brought back Bob Dylan's "Desolation Row," which hadn't made it through my first edit. At 2 a.m., I sat weeping over my laptop; I was like Debra Winger in Terms of Endearment: adding items into the grocery cart after the clerk told me that I couldn't afford the items I already had.

This approach clearly wasn't working, so I made "my personal favorites" the litmus test. I took no prisoners, editing out a lot of "classics" in some cases to make way for "guilty pleasures." So, Sam Cooke remained at three songs, but I could only cut down my favorite retro new-wave band, the Sounds, to four songs.

What kind of freak has more songs by the Sounds than Sam Cooke? I don't know, but that question tends to come up a lot in the morning, when I look at myself in the mirror.

What the iTunes taught me...so far

After another three, painful edits, I have cut the songs down to 1789 - still, over 700 more than my goal.

I've memorized most of the songs in the list, I've looked at them so many times. I've lost the ability to judge the difference between a "good" and "bad" song. I'm tired of iTunes. I'm tired of music. Mostly, I'm tired of trying to decide whether the Beatles' "Happiness is a Warm Gun" is a better song than "I Want to Hold Your Hand."

And here's what I'm left with:

I've condensed the entire Beatles catalogue to just 35 songs. Elvis Costello is at 28 songs. Bob Dylan stands at a paltry 11 songs. The Clash are at 14, the same as the Who. Lou Reed has 18 songs, not including 10 by the Velvet Underground, his first band. The Rolling Stones were never one of my favorite bands, but that I cut their entire output to seven songs is outrageous to even me.

My favorite contemporary band is the Magnetic Fields, which sits at 29 songs, probably because their album, 69 Love Songs, has - you guessed it - 69 great songs on it, all of them quite short.

The Ramones are one of my favorite bands of all time. They sit at 10 songs. New-wave pioneers, Sparks, are well represented with 29 songs. The band has released a stunning amount of material over the years, and bucked the rock and roll trend by getting better with time. A lot of people hate Sparks, but if I'm true to the songs I love, that's how it plays out. How embarrassing.

While going through the CDs, I was regularly surprised by a band or album that sounded really great - way better than I remembered. So, it was particularly painful to cut Yo La Tengo to two songs, Big Star to 11, and Young Marble Giants to five.

One of my favorite punk bands, the Dictators, is reduced to two cover songs - "California Sun" and "I Got You Babe." Ugh. What the hell was I thinking?

In a bid to show that "diversity is the spice of life, I've also included a handful of my favorite TV themes (the original Bob Newhart Show, Rockford Files, Three's Company, etc.), some Schoolhouse Rock, and showtunes for good measure.

I love a lot of classic blues, gospel, and jazz, but I've left these out, partially because they work best as pieces of a full album, but also owing to some of the early blues records' poor recording quality, which is jarring when shuffled with "the hits of the 60s, 70s, 80s, 90s, and today."

I recall making a mixed blues CD for a relative featuring Washington Phillips, Bessie Smith, and Robert Johnson. I was dismayed when she said, "I don't like it; it sounds like music from the Little Rascals." Ugh.

Now what? Help a broken man...

So, here I sit, broken by iTunes. I'm still determined to get the songs down to my original goal of 1,000 favorites, but not sure how to proceed, being a broken man and all.

Possibilities:

1. Include only the songs that were released as singles.

2. Incorporate a three-song-per-band maximum.

3. Incorporate a three-song-per-band maximum with exclusions for the Beatles, Elvis Costello, the Who, and any other band that's been recording for more than 20 years.

4. Ditch anything that's not "rock and roll."

5. Throw my hands up in the air and get a life.

6. Insert your idea here.

In the meantime, you can find me running around the track at Kelvin School. I'm the guy with the portable CD player.