Learning to Fly (Pink Floyd). 40 Songs for 40 Years, 1987

This record really hasn’t held up well for me (it’s an OK David Gilmour solo album, I guess), but it earns its spot on the list because this is the first—and only—big rock show I ever went to. A few months later, I turned into a proper music snob, and by the time I was in college, I wouldn’t even think about going to a show with more than 300 people.

Like thousands of other kids, I waited by the phone until the instant tickets went on sale. I later learned TicketMaster had reserved the good tickets for scalpers and industry insiders, so no amount of speed dialing could get me a good seat. I was stuck in the nosebleed section.

My dad—a huge Pink Floyd fan to this day—said he’d drive me and my friend to the show, but since the tickets had already sold out, he couldn’t get a seat. With the full confidence of the totally naïve, I assured my dad that surely someone would have a seat to sell before the show. Dad was understandably skeptical but agreed to go along anyway—partly out of hope that I was right, and partly just to keep an eye on me.

When we got to the show, I walked up to a guy who clearly had a ticket to sell—really good seats, he said. I was too savvy to believe this, but he only wanted face value, so that was good enough for me.

My friend and I went off to our seats high above the stage floor. My dad found his seat, too: sixth row, center.

Big Time (Peter Gabriel). 40 Songs for 40 Years, 1986

Contemporary pop music is distended folk art, amplified (acoustically and culturally) to grotesque proportions. Big Time uses this to full ironic effect, as a fabulously wealthy international superstar sneers at the ambition that made his success possible.

Which made it the perfect soundtrack for my first year of high school, filled as it was with the shiny, attractive children of shiny, attractive professional parents. While my friends and I would have been quick to protest that we were different, the truth is that we breathed the same air as everybody else; even the self-identified rebels got a good night’s sleep before their SATs.

The archetype of success in my high school was an anodyne omnicompetence that proved an excellent preparation for my years as a consultant. You do what powerful people want you to do, and they reward you. Eventually, you become powerful, and people do what you tell them to do. And just like Peter Gabriel (and me), you can play this game with an insulating layer of ironic detachment that separates you from the pathetic striving ambition of everybody else. Neat trick, yes?

Nine years after this song came out, I had started my first real job. I sat at my Steelcase desk, with my many-buttoned office phone majestic and beige before me. In one of my first acts as a professional management consultant, it was time to record my outgoing voicemail message.

There was only one way to begin:

“Hi there!”

Jellicle Songs For Jellicle Cats (Andrew Lloyd Webber). 40 Songs for 40 years, 1985

Like nearly all adolescents, I wanted to listen to music that drove my parents crazy. They didn’t make this easy: both my parents have cool record collections and pretty broad taste. It was thus useful to learn that my dad couldn’t abide Andrew Lloyd Webber. Armed with this, I repeatedly listened to Cats and Jesus Christ Superstar, and I extolled their virtues at every opportunity.

My mom was more sympathetic to this particular musical enthusiasm, and she took me to see the Los Angeles touring production of Cats for my birthday. I loved it. My grandma was visiting at the time and she came along, too. Much to my mom’s annoyance, Grandma was overcome by the darkened theater and fell right asleep.

Even at the time, I thought Memory was overwrought, and I’ve since expanded that assessment to include pretty much this whole show. It’s one of the few musical obsessions that I’ve really soured on. Nonetheless, I credit Andrew Lloyd Webber with introducing me to the poetry of T. S. Eliot. Toward the end of my Cats kick, I picked up a copy of The Four Quartets in the school library. Once I’d gotten over my confusion that this came from the same guy who wrote Old Possum’s Book of Practical Cats, I fought my way through Burnt Norton. This gave me the first real inkling of what poetry could be, which has proved to be a considerably more enduring legacy.

White Lines (Don't Don't Do It) (Grandmaster Melle Mel). 40 Songs for 40 Years, 1984

Welcome to the awkward adolescence I promised earlier.

I entered seventh grade as a weird, nerdy, chubby kid. It sucked, and I remember this year as almost unbearable.

Of all the records that were released in 1984, the one that probably would have helped me the most was Zen Arcade by Hüsker Dü. Loud, alienated, and very angry, it would have been the perfect soundtrack. Sadly, I wouldn’t hear it until college.

Instead, what I really remember from this year were the songs I heard at dances, where my adolescent awkwardness attained a crystalline purity that makes this song ironically apt.

White Lines was a massive club hit with a cynical anti-drug veneer added to make it commercially viable in the heyday of Nancy Reagan’s Just Say No program. Given the unrelenting wholesomeness of my junior high social life, I’m surprised I heard it so often.

I was way too square to really get this song at the time. Instead, this song made me want to dance and gave me the fleeting illusion that I could be one of the cool, beautiful people. In seventh grade, I wished that feeling would last forever.

Billie Jean (Michael Jackson). 40 Songs for 40 Years, 1983

Speaking of things that weren’t cool. This is the first record I bought with my own money. To my credit, I also bought The White Album at the same time, which redeems things somewhat.

It’s probably just as well that I didn’t know that this song was about disputed paternity. What I did know is that the record was really fun to dance to. I was also fascinated by the stripped-down drumming on this record and how much discipline Ndugu Chancler must have had to play essentially no fills at all. Nowadays, such things are handled by machines, and records aren’t as much fun to dance to. Alas.