20) “Bad”— U2, 1985. A terrifyingly gripping song, mixing tragedy and hope in one six-minute swell. I never wanted to like U2 in the mid-80s when they started to get huge—just because, I guess. But watching Bono do this at LiveAid led to a grudging “Mm hmm” from me. And then watching it a few years later during Rattle and Hum put me over the edge. No pun intended (heh...The Edge. Heh.) Anyway, it's symphonic in the way it builds to a climax and then lets up very slowly, very deliberately. Sad and astonishing. “True colors fly in blue and black, blue silken sky and burning flak.”
19) “Red Shoes”—Elvis Costello, 1977. Geek bravado at its apex. As a geek who likes to think he’s brave (I’m not), it kinda speaks to me. Usually saying, “Get out of my face.” But still I love the way it smiles and hisses at the same time. “I used to be disgusted, now I try to be amused.”
18) “America”—Simon and Garfunkel, 1968. In college I took off one night on a plane ride halfway across America and spent a couple of days on the road, from Texas out to New Mexico, searching for…something. I never found it, and neither does the narrator of this song. But the search for something real and personal continues, Paul Simon put together a travelogue of the soul here. “'Kathy, I’m lost,’ I said, though I knew she was sleeping.”
17) “Me and Bobbi McGee”— Kris Kristofferson, 1971. This probably should be higher, but being on this list should be good enough for now. It’s Jack Kerouac condensed to four lovable minutes. And it’s a genuine piece of my childhood—on every car trip we’d take as a family, my parents had this playing on the tapedeck. It’s now embedded, as it should be. Love, adventure, and loss without regrets, a landmark tale of affection that takes us straight across the U.S.A. “I’d trade all my tomorrows for one single yesterday, holding Bobbi’s body next to mine.”
16) “The Pretender”—Jackson Browne, 1976. The man knew pain. And he knew how to write about it. Self-deprecating and self-realizing without an ounce of self-pity. My favorite Jackson Browne song. “We’ll get up and do it again. Amen.”
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