Solo work only
  1. Hearts and Bones
    It's the song that "Graceland" is a sequel to. It's about the dissolution of his marriage with Carrie Fisher(!), and it's just about the most devastating and beautiful thing I can think of. The arc of a love affair.
  2. Graceland
    The Godfather Part II to Hearts and Bones's Godfather.
  3. I Know What I Know
    The very next track from Graceland, which is the best song of all time to use African rhythms to capture the feeling of being a little uncomfortable at an NYC party. Contains the lines "There's something about you that really reminds me of money," and "Aren't you the woman who was recently given a Fulbright?"
  4. Late In The Evening
    He's describing his entire childhood. Talks about being at a "funky bar" and having "stepped outside to smoke myself a J." Also, it serves as the opening credits to the movie One Trick Pony, for which Simon wrote the screenplay, and in which he stars. Lou Reed plays a cheesy record producer that forces him to add a string section to one of his songs.
  5. Kodachrome
    "If you took all the girls I knew when I was single, and brought them all together for one night, I know they'd never match my sweet imagination." True that.
  6. Rewrite
    This song is from 2011 so nobody will agree with me, but it's fucking great. It kind of sounds like the Dirty Projectors and it's got lyrics about writing a screenplay. And dude was like 70!
  7. Mother and Child Reunion
    The first track on his first solo album after splitting with Garfunkel is straight up reggae.
  8. The Obvious Child
    A beautiful and hilarious song about a stand up comic in Williamsburg who gets an abortion. Jk
  9. You Can Call Me Al
    Only Tom Petty can handle songs with three full verses as deftly as this. Also, the video is probably Chevy Chase's best work.
  10. 50 Ways to Leave Your Lover
    The drums sound so so good. The only problem with this song is that it actually only lists five ways to leave your lover. Slip out the back, make a new plan, no need to be coy, hop off the bus, drop off the key. And that's generous. "No need to be coy" is not really a way to leave your lover. You know, people love to pick apart "Ironic," but this song's lyrics are as bad at living up to its didactic title.
  11. Bonus: Train in the Distance
    By popular demand, and I couldn't agree more. I have teared up many a time at the depiction of those islands of intimacy in the vast sea of pain that is a breakup: "But from time to time he makes her laugh. She cooks a meal or two." Everybody thinks it's true!
  12. Bonus: Diamonds on the Soles of Her Shoes
    Also suggested by more than one person, so I'm adding it here. This song is maybe directly responsible for Ladysmith Black Mambazo's long career as popular recording artists and writers of Lifesavers jingles.