Top 10 Paul Simon songs

I’m calling this a list of my favorite Paul Simon songs, but these are almost exclusively Simon and Garfunkel songs. To be honest, I’ve never been a particularly big fan of Simon’s solo work. He’s got plenty of nice songs spread throughout the years, but very little that rises to the level of his songs from the sixties. Still, I had to expand things to his whole discography simply for the sake of Graceland.

10. The Sun is Burning (Wednesday Morning, 3 A.M.)
I have a somewhat weird fascination with songs about apocalypse. In high school I collected them pretty relentlessly, and this was in a pre-MP3 world, too, so it was pretty hard to compile them. For obvious reasons, a lot of these songs come from folk and from metal. In each case it makes sense, but it’s kind of a weird pairing.

Anyways, of the entire set, this one is probably my favorite song. It’s just so achingly beautiful. Until the final two verses, there’s no hint whatsoever that it’s even going anywhere dark.

9. Diamonds on the Soles of Her Shoes (Graceland)
I’ve always had a big crush on the woman in this song. There’s something effortless in the dualism of it. You could think of her as careless (a Gatsby character), so rich that she has diamonds even on the soles of her shoes. But you can also think of her as rich in spirit, not ashamed of who she is and where she’s from, but feeling no need to flaunt it. She wears the diamonds because…why not. But she wears them on her soles, where no one will ever see them, where they are trodden on every day. “She’s a rich girl, she don’t try to hide it, diamonds on the soles of her shoes.” But later, “She said you’ve taken me for granted because I please you, wearing these diamonds.” And you wonder…was she cast out or did she leave? And is it possible that she’s far happier than she could ever have been in high society now that she’s out on the streets with the poor boy? There’s no way to no for sure, but that’s what makes it such a great song.

Because here’s the thing, the best he can do is put on a new set of clothes and some aftershave. He can’t take her out on the town, maybe doesn’t even have a home. It’s sad and discouraging, but also beautiful. Because suddenly “by the bodegas and the lights on Upper Broadway,” it’s no longer diamonds on the soles of HER shoes. It’s diamonds on the soles of THEIR shoes.

And then he just says ‘oooooooooo’ as if everyone knows what he’s talking about…because what else can you say?

8. The Only Living Boy in New York (Bridge Over Troubled Water)
Some of the best ‘ahhhhs’ ever recorded. The song is Paul saying goodbye to Art (they originally went by the name Tom and Jerry), and it’s pretty much the sweetest song about a band breaking up you’re ever likely to hear. No hard feelings, just an expression of joy about what they were able to do together, even if it was for only a short time. And yet, it’s by no means a happy song. You can’t regret what needs to be, but you can still feel the pain of its loss.

7. Flowers Never Bend With The Rainfall (Parsley, Sage, Rosemary, and Thyme)
It’s such a beautiful and simple melody, and the harmonies are gorgeous. The line that really gets me is: “I am blinded by the light / Of God and truth and right / And I wander in the night without direction.”

6. The Sounds Of Silence (Sounds of Silence)
I love the original, quiet, acoustic version of this song. But there’s no denying the power of the electric one. The juxtaposition of the electric jangle just makes the refrain against the sound of silence reverberate that much more powerfully.

You might not know this, but the drums, bass, and electric guitar overdub were recorded by Bob Dylan’s studio band in the immediate aftermath of them recording “Like a Rolling Stone.”

That kind of blows my mind, really. To record one of the finest records in history, and then on a producer’s whim add the crucial bits to a relatively unknown track by some duo with a goofy name (who had broken up at this point), which then springs that song to #1…

It’s crazy to think that Paul Simon might never have become famous if not for Tom Wilson asking for those overdubs – completely without the knowledge of Simon or Garfunkel.

5. The Boy in the Bubble (Graceland)
I was too young to experience Graceland firsthand, but I can easily imagine what it would have been like to hear it fresh. For all the nice songs in Simon’s catalog from between Bridge Over Troubled Water and Graceland, it was certainly a comparatively weak period. You could easily be forgiven for thinking that there were no more great songs left in him.

And then he went to South Africa, causing controversy for his violation of the sanctions. What he came back with was a record that mixed the classic Paul Simon songwriting skill with world music, and wrapped it all up in a beat that feels very much a product of the mid-80s (with all the good and bad implications that come with that thought). It’s really pretty crazy that it works.

But it doesn’t just work, it’s mind-blowing. It’s a revelation.

This doesn’t sound like Simon tacking on some ‘world’ sounds in order to spice things up. It sounds like him getting caught up in the tempest of sounds and feelings and doing his best to find himself within it. It’s distinctly a Paul Simon album, but there is simply no way that anything remotely like this song could have been produced out of a different milieu. It’s what makes his voice sound so perfect on the line “these are the days of miracle and wonder” – because you can tell how genuinely he feels it.

4. Kathy’s Song (Sounds of Silence)
One of the very finest love songs ever written. Also one of his finest pieces of poetry. It’s a product of a very specific moment in Simon’s life, and yet it’s also completely universal. It’s simply the feeling of quiet desperation, the lack of certainty that you will ever amount to anything or that it will ever make sense. And it’s the way that love helps sustain in those moments. It’s not that we’re rescued by love; it’s just that the struggle and the pain is somehow redeemed, made worthwhile.

3. The Boxer (Bridge Over Troubled Water)
This song was Paul Simon’s version of Born to Run. It famously took over 100 hours for them to produce a recording that satisfied him, and he drove everyone crazy trying to micro-manage it. He was also tremendously unhappy with the wordless chorus, which was only meant to be a placeholder until he figured out the right words. But for me, that’s part of the serendipity of the song. There’s something ineffable about those repetitions of ‘lie la lie’ that couldn’t possibly have been captured with lyrics.

This will, forever I think, be the benchmark against which coming-of-age songs are measured. The story is so sad and desolate and sparse; it combines beautifully with the huge cannon-fire drums, the strings, the rising tide. Simon’s finger-picked guitar is wonderful here, too.

You know, the 60s almost defy belief. So much took place in so short a time. And when we think about ‘the 60s,’ really we’re thinking about a period even shorter than a full decade. You might say that the 60s started in Dallas, 1963 and ended in Woodstock, 1969. But for me, I can’t help but think that the 60s really ended with just two little musical moments. First, The End from The Beatles. And second, the final verse of this song. The boxer stands alone and cries out “I am leaving, I am leaving” – but the fighter still remains. And curtains draw close on the decade.

2. Graceland (Graceland)
In one sense, it’s a fairly straightforward song about broken hearts and the difficult task of rebuilding a life. In another, it’s about the existential meaning of love, and what it means to live your life FOR something as opposed to simply existing. And mixed in with all of that is the thoughts of fading empires and the politics of identity. All in all, it’s really nothing more or less than the sound of hope which shines through in the darkest of times – not always (or even often) successfully. But trying nonetheless.

It opens: “The Mississippi Delta was shining like a national guitar / I am following the river down the highway through the cradle of the civil war.” That is pure poetry, evocative and beautiful. And it establishes the multi-layered themes. Traveling with the one who loves your most truly (your son) on a pilgrimage to the roots of rock and roll, seeing the country that tore itself apart and slowly (very slowly) began to heal itself over the centuries, and thinking about your own world being blown apart.

So it’s no surprise when you hear the next verse:

She comes back to tell me she’s gone
As if I didn’t know that
As if I didn’t know my own bed
As if I’d never noticed the way she brushed her hair from her forehead
And she said losing love is like a window in your heart
Everybody sees you’re blown apart
Everybody sees the wind blow

The deep, intense sadness. The slight sense of bemusement and disbelief. The realization that you knew all along but just couldn’t quite admit it. And the falling down of walls that you have tried desperately to erect between your interior and the world outside.

There aren’t answers here, but there really couldn’t be. The important thing is the searching, not what you will find.

1. A Poem on the Underground Wall (Parsley, Sage, Rosemary, and Thyme)
It’s the other side of The Sounds of Silence, the poetry of the underground. When there is nothing except the suffocating silence, a simple scrawl of four letters is all that’s left. It challenges us to mark the violence, to remain attuned to the impossibility of representation, to wrestle ourselves out of a stupor.

And what is the word? For years I just assumed it to be an obscenity. An expression of rage to mark the hypocrisy. The truly obscene, it says, is the advertisement that has been written over. No matter its connotations, a word is still an act of poetry. But advertisements are all the more disgusting because they hide themselves under the clean veneer of happy consumption.

But after years of listening to the song, it suddenly dawned on me that there’s another equally plausible word, something that stands in direct opposition: “love.” I think there’s a deliberate ambiguity here. And it’s not just an ambiguity of the wording, but also of the possibility for meaning at all.

The crayon is a rosary; it’s an object to signify devotion. We hold onto it in order to grab hold of something stable in the midst of chaos. Held with true belief, it transforms the bearer. It gives us a sense of deeper purpose. But that purpose is not found in the object but comes through its use. Individual words, individual prayers, these have no meaning by themselves. They obtain meaning through their context.

The word scrawled across the advertisement is only poetry because it is there, in that place, at that time. What it means depends on who we are every bit as much as it depends on what it says.

In my heart of hearts, I can see the bold letters screaming ‘fuck.’ And yet, in that desperate plea, I can hear a whisper, a quiet voice reminding us that the WORD doesn’t matter. Salvation is not in the word; it’s in the act. Even more, it’s in the faith that lies behind the act. The faith that one word, scratched onto a subway wall, can still be heard. And that is, above all, faith in the power of ‘love.’

Honorable mentions
11. America (Bookends)
12. I Am a Rock (Sounds of Silence)
13. The Dangling Conversation (Parsley, Sage, Rosemary, and Thyme)
14. Homeward Bound (Parsley, Sage, Rosemary, and Thyme)
15. Mrs. Robinson (Bookends)