10 “Paid In Full” – Eric B. & Rakim, 1987.
I’ve told this story before. In the fall of my year in the Bay Area, I discovered a hip-hop show on Stanford’s campus radio station, KZSU. The only problem was we lived way across the Bay, and I could only pick the show up on a small, portable radio that had a three foot antenna. So, to record the shows, I had to run a cord to an old-school tape recorder (this was 1987, so it wasn’t so old school at the time). That left me with a fuzzy, mono tape of the latest songs from New York and L.A. One Sunday I heard “Paid in Full,” listened to it about a million times, and bought said album a couple weeks later. Somehow I was one of the first students at San Leandro High School to be hip to Eric B. & Rakim, and, in a cruel twist of fate, became very popular in my final weeks at the school as cool guys asked me either to dub a copy for them, or if they could borrow it for a night to make their own copy. Every time I hear this, I think of my boy Charles Terrell from Oak-town and hope that the last 20 years have treated him well.

9 “How Soon Is Now?” – The Smiths, 1984.
I went back-and-forth between this and The Smiths’ “There Is A Light That Never Goes Out,” many times. While both are typical Morrissey songs about being an awkward outsider, unsure of your place in the world, “Light” almost has an upbeat feel to it. It’s more of a “Life sucks but it doesn’t suck quite as much because I’m with you” song. “How Soon Is Now?” though, is all gloom and doom. It’s one of the most depressing songs ever, in fact. Throw in the brilliant cover of “Light” by Neil Finn and Friends, and I thought it had won the battle.

But, as good as “Light” is, “How Soon Is Now” is completely unforgettable. Even if you can’t totally sympathize with Morrissey’s plight, chances are at some point when you’ve been down about your romantic life and heard this song, the line below just destroyed you for a moment or two. And Johnny Marr’s guitar? Effingbrilliant.

8 “They Reminisce Over You (T.R.O.Y.)” – Pete Rock & C.L. Smooth 1992.
1992 was a watershed year in music. Old genres were being pushed aside as new ones developed and radio was a fascinating mix of styles as program directors and listeners attempted to figure out what was what. I will always look back on that summer fondly, as my personal soundtrack featured hip-hop (Arrested Development among others), R&B (Mary J. Blige), the emerging grunge sound (Pearl Jam), alt rock (R.E.M., Toad the Wet Sprocket, The Cure), and this song.

It’s strength comes from both its content (a tribute to a fallen friend, a biographical sketch, a tribute to those who survive rough times and strive to make their lives better) and its production. It is built around a wonderful, haunting, looped sample from Tom Scott’s “Today.” Throw in a hip-hop beat and you have one of the most unforgettable melodies of the 90s. I owned (I may still own it for that matter) the cassette single for “T.R.O.Y.” and kept it in my vehicle until just a few years ago, when we transitioned to two cars without cassette players. It was a comfort to always have it there, ready to pop in when radio or CDs let me down.

7 “True Faith” – New Order, 1987.
This is one of the few classic, 80s alternative rock songs that I loved in its time, rather than learning to appreciate it later when my musical tastes shifted. The driving bassline and that crazy ass video had a lot to do with it.

At first glance, this song is about growing up and growing apart. Further research shows, however, that Bernard Sumner was in fact singing about heroin abuse. A skittish record company forced him to change one key lyric, although in concert he always sang his original line. “Now that we’ve grown up together, they’re afraid of what they see,” was intended to be “Now that we’ve grown up together, they’re all taking drugs with me.” Doesn’t seem like a big deal now but, hey, it was 1987.

“True Faith” serves as a transition point in British music, from the pop/synthesizer sound of the 80s to the more guitar-driven sound that would emerge from Manchester when The Stone Roses burst on the scene two years later.

6 “Clampdown” – The Clash, 1979.
I had a hard time picking a Clash song. So many of their songs share common themes and sounds that it can be difficult to separate them. But I’ve always admired the perspective of this song, one of the few moments when The Clash’s bluster and political agenda were focused on an issue they actually understood and could have an impact on: the rise of the racist, far right in Britain.

5 “Corduroy” – Pearl Jam, 1994.
I would imagine people react to this song based on their like or dislike for Pearl Jam. The haters will say, “That’s when Eddie’s whining got out of hand and I tuned them out.” The fans point to this as the moment that the band decided to claim control of their career – and in turn their lives – and damn the consequences. So, it’s a little ironic that, aside from all the classic singles off their first album, this was one of their biggest and most successful singles.

Named for the fashion line knock offs of the thrift store jacket Eddie Vedder wore in the video for “Jeremy,” this was indeed when the band put the brakes on the hype machine and refused to carry the burden of Biggest Band In The World. Vitalogy is their darkest, angriest album, and this song was its center-point.

4 “And Your Bird Can Sing” – The Beatles, 1966.
There are several acts in my list for which it was difficult to narrow their body of work down to a single song. But the Beatles? It was damn near impossible. I have 25 Beatles songs in my iTunes library rated as five stars. How do you not pick “Yesterday”? Or “Tomorrow Never Knows”? Or “Strawberry Fields Forever”? Or “A Day In The Life”? And so on. Perhaps it was a bit easier for me, as I only became a Beatles fan within the last 6-7 years, so I’ve been able to take all their music in during a relatively brief time span, putting everything on equal ground, more or less.

All those, and several others, are fine choices. But this song always sticks out for its simplicity, its place in the band’s history (side one of Revolver, the sweet spot of their career), and the sense of playfulness and life in it. This is just a fun song that you want to hear over-and-over again.

3 “One” – U2, 1992.
Here’s where we had my last second shake-up. For years I’ve struggled to pick my favorite U2 song, always wavering between “One” and “Bad.” For most of the past two months, I’ve had “Bad” slotted into my top five. Then, suddenly, a week ago, I changed my mind. I’m not really sure why, as “Bad” is still brilliant. Perhaps it is because it has more ambiguous meanings, and thus more difficult to relate to. Perhaps it’s because Bono has said it’s about a friend who was a heroin user, something I thankfully haven’t experienced.

“One,” on the other hand, is more direct. If you’ve been through tough romantic times, chances are you can find something in this song that hits close to home (I’m sensing a theme in the countdown). Bono has often struggled as a lyricist, at times getting his message across more through sound than words. This has to be one of his finest efforts, though.

And then there is the new, post 9/11 meaning of the song. Following the attacks, U2 ended their encores on the Elevation Tour with a lengthy tribute to those who had died. Covering “One,” “Peace On Earth,” and “Walk On,” (at least when I saw them in Kansas City), the names of all who had died that day rolled on the screen behind the band. It had only been two months, and feelings were still raw, but it was the most emotional moment I can remember at a concert. In fact, for a long time after the concert, my wife couldn’t listen to “One” because of that new connection.

2 “Karma Police” – Radiohead, 1997.
You may remember my countdown of my five favorite albums about a year ago. You know, the one I never completed by writing up <em>London Calling</em>. It turned out, as I listened to <em>London Calling</em> for a couple weeks after listening to <em>OK Computer</em> for a similar amount of time, I realized I liked <em>OK Computer</em> more. This song is one of the reasons.

On an album about how technology and corporations and consumerism crush the individual, this was the center-piece: an Orwellian warning of what could happen to those who dare to resist a system run amok. It also serves as a bookend to the 90s, ending what “Smells Like Teen Spirit” and <em>Nevermind</em> began.

The title is menacing enough. When you hear Thom Yorke sneer the lines below, it’s even more chilling.

1 “Don’t Dream It’s Over” – Crowded House, 1987.
Neil Finn’s best songs are those that put his John Lennon influences right out in front: Love songs that speak not just of being in love, but also acknowledge that we fail each other in ways big and small each day. Yet to be truly in love, you accept and move past those missteps. This is, inarguably, his finest effort in that vein.

Music is important to me, and my favorite songs often serve as the soundtrack to parts of my life. This always takes me back to the spring of 1987, when I was struggling to fit in at my new school in California. The melancholy side of the song resonated with a 15-year-old who was lonely and having a hard time finding a social circle to fit into. At the same time, the idea of persevering through troubled times Finn also sang of helped me to keep trying to make friends and find my way. And 21 years later, I still think that single-beat pause in the final chorus is brilliant.