10 Best Paul Simon Songs

Paul Simon’s songs are part of the American landscape, a thoughtful man documenting his inner dialogue in popular song. From Simon and Garfunkel songs like ‘America’ and ‘Bridge Over Troubled Water’ to solo songs like ‘American Tune’ and ‘Graceland’, his songs capture both the American zeitgeist and his own personal journey. He’s also covered a lot of musical ground – his early work is grounded in folk, but he explored textures and styles from Jamaica, South Africa, and Latin America.

This list only covers Simon’s work as a solo artist. While Simon has released music slowly since 1975’s Still Crazy After All These Years, there’s still more than 50 years of solo music to draw from, from 1965’s The Paul Simon Songbook to 2017’s Stranger to Stranger. There’s an embarrassment of riches – there’s no room for ‘You Can Call Me Al’, ‘Kodachrome’, ‘Me and Julio Down By The Schoolyard’, or anything from the Grammy-winning Still Crazy After All These Years. I also had to exclude personal favourites like ‘Loves Me Like A Rock’, ‘Wristband’, ‘Under African Skies’, and ‘The Obvious Child’.

10 Best Paul Simon Songs

#10: Something So Right

from There Goes Rhymin’ Simon, 1973
This lush slice of soft-pop is drawn from Simon’s second record of the 1970s. It presaged Simon’s move into jazz-flavoured territory on 1975’s Still Crazy After All These Years with its chord structure, while Quincy Jones wrote the lush string arrangement. Annie Lennox recorded ‘Something So Right’ on her 1995 covers album Medusa.


#9: Wartime Prayers

from Surprise, 2006
Simon’s take on 9/11 took half a decade to emerge. Combining disparate musical genres isn’t unusual for Simon, but it’s particularly pronounced here – along with Simon’s trademark introspective folk-rock, Brian Eno adds electronics, jazz legend Herbie Hancock is on piano, while gospel group the Jessy Dixon Singers are on backing vocals. It’s a very strong late-period piece – with a hummable tune and some of Simon’s most cutting lyrics – “Because you cannot walk with the holy/If you’re just a halfway decent man”.


#8: Late in the Evening

from One Trick Pony, 1980
Simon’s 1980 movie One Trick Pony was unsuccessful, and the accompanying Simon album was one of his weaker efforts. But the best thing to come out of the project was the lead single ‘Late in the Evening’. Simon recalls his own musical apprenticeship, backed by cowbell, a great Steve Gadd drum rhythm, and a Mariachi horn arrangement from Dave Grusin.


#7: The Cool, Cool River

Paul Simon Rhythm of the Saints

from Rhythm of the Saints, 1990
Rhythm of the Saints was the sequel to Simon’s massively successful 1986 album Graceland, with Simon exploring Latin American sounds and rhythms. While its dense lyrics made it a more difficult listen, much of it is among Simon’s best work. ‘The Cool, Cool River’ is a journey of self-reflection, with anger in the terse verses and hope in the glorious and uplifting coda. I specifically recommend the version from 1991’s Paul Simon’s Concert in the Park – the coda is punchier than on the studio version.


#6: Peace Like A River

from Paul Simon, 1972
Taken from Simon’s first post-Simon and Garfunkel album, ‘Peace Like A River’ is a simple arrangement with Simon backed with congas and Joe Osborne on bass – probably a relief for Simon after the grandiose arrangements of Bridge Over Troubled Water. In this simple setup, Simon’s acoustic guitar work is impressive. The title is taken from The Bible, and the song is like a satisfied look back at the progress made by civil rights activists in the 1960s. It acknowledges their work is far from over in the “I’m gonna be up for a while” coda.


#5: Graceland

from Graceland, 1986
Simon’s career was in turmoil after 1983’s Hearts and Bones failed to make it into the US top 40. Listening to a tape of street music from Soweto, Simon became interested in South African music and flew to Johannesburg to jam with local musicians. Back in New York, he worked the jams into full songs. While expectations were low, Graceland became Simon’s best-loved album.

Simon felt awkward about taking the album’s title from the name of Elvis Presley’s home, but realised that in the song it had become a metaphor for a state of grace. ‘Graceland’ contains some of Simon’s best lines, addressing his failed marriage to Carrie Fisher – “And sometimes when I’m falling, flying/Or tumbling in turmoil I say/”Whoa, so this is what she means”/She means we’re bouncing into Graceland.” Simon’s musical heroes, The Everly Brothers, appear on backing vocals.


#4: Mother and Child Reunion

from Paul Simon, 1972
Simon had dabbled in reggae before – ‘Why Don’t You Write Me’ from Simon and Garfunkel’s Bridge Over Troubled Water was recorded with US studio musicians, but it ended up as a “bad imitation”. For his solo debut, he travelled to Jamaica to record ‘Mother and Child Reunion’ with Jimmy Cliff’s backing band. The title was inspired by an item on a Chinese restaurant menu (a meal with chicken and egg together) and the lyrics were inspired by the death of Simon’s pet dog.


#3: American Tune

from There Goes Rhymin’ Simon, 1973
When Nixon was re-elected in 1972 and the Vietnam war was dragging on, Paul Simon was disillusioned. In 1971, he’d contributed a quatrain for Leonard Bernstein’s Mass – “Half of the people are stoned and the other half are waiting for the next election/and half the people are drowned and the other half are swimming in the wrong direction”. American Tune continues those sentiments – it’s a lament for a nation that had lost its way. ‘American Tune’ takes most of its melody from a song published in 1601 by Hans Leo Hassler, also used by Bach for St Matthew’s Passion. The melody of the evocative bridge (“I dreamed I was flying”) was written by Simon.


#2: Rene and Georgette Magritte With Their Dog After The War

from Hearts and Bones, 1983
Rene and Georgette Magritte With Their Dog After The War’ was inspired by a photo bearing the same caption. It has a dream-like quality as Simon imagines the Belgian surrealist painter and his wife surreptitiously enjoying 1950s doo-wop music. It’s essentially 1980s sophisti-pop – Richard Tee’s Fender Rhodes fills are lovely, and the harmonised chorus is gorgeous. Simon is joined by then-wife Carrie Fisher in the music video, where they portray the Magrittes.


#1: Diamonds on the Soles of Her Shoes

from Graceland, 1986
Like the rest of Graceland, ‘Diamonds on the Soles on Her Shoes’ helped introduce African sounds to the western world. Male choral group Ladysmith Black Mambazo provide their distinctive backing vocals, while . Much of the song’s appeal comes from the distinctive African musicianship – Ray Phiri’s guitar licks and Bakithi Kumalo’s jazz-inflected fretless bass work are both gorgeous. The closing refrain of “ta na na na” is the best hook in Simon’s catalogue, while Simon’s lyrics are hilariously ambiguous: “As if everybody here would know/What I was talking about/Talking about diamonds on the soles of her shoes.”

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Did I leave out your favourite Paul Simon track?

43 Comments

  1. Great playlist by a great artist. Glad to see “Graceland” is well represented. I really loved that album when it came out (and still do) and saw Simon during the supporting tour at the time. Seeing these African musician perform on stage and the joy they projected was something else. A tune I would have included in my top 10 is “50 Ways to Leave Your Lover”

  2. I actually don’t know all of these. “The Boxer” is my overall number one and “Cecelia” and “the Sound of Silence” would be my 2 and 3.

    “call me Al” is the best song on Graceland. Yes it was a pop hit but that doesn’t take anything away from it.

    • I like ‘You Can Call Me Al’ fine – it’s just there are 5-6 amazing songs on Graceland and I couldn’t fit them all. Under African Skies, Boy in the Bubble, and I Know What I Know are all great too.

  3. Once again you’ve thrown down the gauntlet and once again I must interrupt whatever I’m doing and respond. I once said on my site that Paul Simon was in rarified air with Lennon/McCartney and Dylan. A (former) reader spent three or four comments trying to somehow change my mind and was ultimately frustrated that his words could not change my opinion. Let me say it here very loudly, very clearly, very definitively – Paul Simon is one of the greatest songwriters not only of the rock/folk generation but who ever lived and he has few peers. He wrote ‘The Boxer’ and ‘Bridge Over Troubled Water’ back-to-back for God’s sake. And then there’s everything else! There, now I feel better.

    As to the list, I purposely avoided looking at yours so it wouldn’t influence mine. When I went through his discography, frankly I didn’t get much further than seriously looking at ‘Rhythm of the Saints’ (from which I didn’t pick anything.) I know there’s good stuff after that (failed play ‘Capeman’) has some nice stuff but I just don’t know those well enough and they don’t resonate with me. Here’s my list:

    10. One Man’s Ceiling is Another Man’s Floor
    9. Mother and Child Reunion
    8. Something So Right
    7. Loves Me Like a Rock
    6. Kodachrome
    5. American Tune
    4. You Can Call  Me Al
    3. Me and Julio Down by the Schoolyard
    2. Diamonds on the Soles of Her Shoes
    1. Graceland

    Honorable mention: Still Crazy After All These Years; 50 Ways To Leave Your Lover; Late in the Evening; Homeless; Under African Skies;

    • We had 5 in common, which is a lot. You could make a pretty good playlist just with Rhymin’ Simon and Graceland.

      I don’t know why Simon doesn’t get put up with Lennon/McCartney and Dylan. He started a few years later, and I don’t think he had as much great stuff in the 1960s and 1970s (especially as he didn’t get going until 1965 and didn’t release much between 1975-1980), but I think he’s clearly outperformed McCartney and Dylan since 1980. He’s maybe just not quite rock and roll enough – more like a detached observer than part of the scene. Not trying to argue, just trying to figure it out.

      • I don’t know if it’s not rock ‘n roll enough. Here’s my thought. Firstly, Dylan exists on another plane. He brought a whole different sensibility to popular music. You could tackle serious subjects! You could make people think. And he has a Nobel which the other guys will likely never get.

        The Beatles were a worldwide phenomenon who not only moved WITH the culture but actually moved the culture. And they wrote a bunch of songs that also pushed songwriting forward.

        My thought is that Paul wrote a tremendous amount of great songs but while S&G were tremendously popular, they weren’t the same level of cultural phenomenon. And I think that like Dickey Betts in the Allmans, Paul was just in many ways overshadowed.

        But history will tell. Simon is the very first person to win the Gershwin prize, McCartney the third. Lennon and Dylan – no.

        But I think you may be underestimating how people appraise Simon. Go read his entire Wikipedia page and see the honors he’s gotten the people who have paid tribute to him. We can argue whether he’s still on the level of Dylan and Lennon/McCartney. But even if it’s Dylan 1, Lennon/McCartney 2 that’s ok. But for me it will forever by Paul Simon 3. And then everybody else.

  4. I got tired of Paul Simon early in life because my father played “50 Ways to Leave Your Lover” non stop.

  5. Oh sorry. I didn’t read that it’s only his solo stuff on your top ten before I responded. As usual I didn’t read the fine print.

    I had a bunch of S and G songs in my comment. Handicapping the whole catalogue would make it both easier and more difficult I imagine!

  6. A nice list Graham, which includes several of my favorites of Simon’s songs. I’m not going to take issue with any of your choices or rankings, as I absolutely hate when people do that with my song lists.

    • I quite like it if people suggest songs I’ve missed or pick their favourite. It’s just if someone’s convinced that they’re absolutely right that it’s annoying. With someone like Simon there’s a vast, strong catalogue that it’s impossible to fit all his great songs into a list of ten.

  7. When Rolling Stone magazine published their “top 100 albums of all time” issue in the late 1980s, they deliberately tried to avoid the “recency bias” by omitting albums that had been released in the prior few years.

    The lone exception they made was for “Graceland”. They claimed it was a chance worth taking .

    I’m sure you can google it all to fact check my foggy memory!

  8. Great list . . . glad to see “Magritte” place so high, it’s my clear and easy #1. I’m probably hit-heavier with my appreciation of his catalog than you are, but what hits they were! I have mixed feelings about “Graceland” (I was heavily into collecting and studying “real” African music when it came out, and it smacked unpleasantly of appropriation to me)(but that could, admittedly, be a function of my own intellectualizing about what I was hearing then, and not liking hearing watered down versions of it winning such plaudits), but “The Boy in the Bubble” is the one song from that album that I could not, and cannot, resist. So my list would look something like . . .

    10. Slip Slidin’ Away
    9. Mother and Child Reunion
    8. Kodachrome
    7. Loves Me Like a Rock
    6. 50 Ways to Leave Your Lover
    5. The Boy in the Bubble
    4. The Obvious Child
    3. Late in the Evening
    2. Me and Julio Down By The Schoolyard
    1. René and Georgette Magritte with Their Dog after the War

    • Graceland isn’t really a pure African album, right? More like a weird hybrid of 1980s pop, Paul Simon, and African jamming. There’s some really cool guitar and bass playing though.

      I’m glad someone else likes Magritte – I thought it was a bit provocative having it at 2nd, but it’s really good.

  9. This one would be a very hard list Graham. I cannot argue with what you picked. For me I would have to include Kodachrome. The one I’m happiest to see on there is Mother and Child Reunion…that is my number 1 Paul Simon solo song…not that it matters but my number 1 Paul Simon song period is America…

    I’m glad you didn’t over load it with Graceland material…I do like that album a lot don’t get me wrong but I’ve seen people do that on his lists. You covered his career nicely with this…as far in the last twenty or so years…I really like “Old.”

    • I’ll do a Simon and Garfunkel list sometime, and America will definitely be on there.

      It’s hard to justify more than 2 slots for an album for Simon – he just has so many good records. I would have liked to include ‘Under African Skies’ or ‘Boy in the Bubble’.

      • That list will be difficult but not as difficult as this one…less of a time span.

        Boy in the Bubble is my go to song off of Graceland. When I heard “The bomb in the baby carriage was wired to the radio” I was won over. I had to get the album after that.

        • My English teacher in high school gave us the first verse to study once. I like the line “it’s a turn around jump shot/It’s everybody jump start” from later in the song.

          • If I hear a clever lyric…I will like the rest of the song…but yes…that one is filled full of them.

    • Once my friend at school publicly mocked me for arguing Take Me To The Mardi Gras was better than Green Day. That whole There Goes Rhymin’ Simon album is great, apart from ‘Was A Sunny Day’.

  10. Loads of stuff here I don’t know, cause I’ve never really listened to Paul Simon beyond Graceland and Hearts and Bones. At the risk of courting controversy here I’m gonna suggest that the 10 songs here are pleasant. I don’t doubt that the songs are well crafted. Same with the stuff with Garfunkel. But, y’know, it’s just my opinion.

      • I can’t disagree with that assessment. Kinda like Don McLean and Jackson Browne in a way… pleasant enough and fine songwriters, but it doesn’t really move me.

  11. Those are all strong choices- narrowing a list to just 10 would be difficult- without thinking too hard the first that comes to my mind as my favorite would be -‘American Tune.’

    • Maybe I Think Too Much for my own good?

      American Tune was my favourite from the 1970s, although I think just about the whole Rhymin’ Simon album is great and a bit overlooked.

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