The 10 Best Paul Simon Songs

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The 10 Best Paul Simon Songs

Keystone/Getty Images

Fifty years ago, Paul Simon wondered how terribly strange he’d feel at 70. Today, after becoming one of the 20th century’s greatest songwriters, he turns 80. Happy birthday, Paul.

Simon began his career as a teenage hitmaker with erstwhile partner Art Garfunkel. The two cut a track called “Hey, Little Schoolgirl,” an Everly Brothers rip-off that made them local celebs at their high school in Queens. They broke up, got back together, and formed Simon & Garfunkel, the most successful musical duo of the 1960s. As the creative force behind the act, Simon wrote a number of all-timers and some sophomoric stuff that sounds like high school poetry. By the time they released swan song Bridge Over Troubled Water, in 1970, Simon had shed the world-weariness of his younger years and matured into an artist capable of anything.

His solo career came next, and has persisted — on and off — for nearly half a century. His style in this era can best be described as numinous. He’s sophisticated, curious, and sanguine. His music is spiritual and it shines like a National guitar. Summing up Paul Simon’s 14-album solo career in 10 tracks was as fun as it was painful. Feel free to disagree (that’s what the comments are for), but remember, one man’s ceiling is another man’s floor.


"The Coast" (from The Rhythm Of The Saints, 1990)

To me, the golden era of Paul Simon is roughly from 1966-1990, ending with his last true masterpiece, The Rhythm Of The Saints. Sure, he put out great music in the time after The Simpsons premiered its second season, but none of it is top-10 material. “The Coast” is a gem on an album that should be as loved by the culture as its predecessor, Graceland. The song’s production is ambitious, showing that Simon is not someone to rest on his laurels following his 1987 Grammy win for Album Of The Year.

Ushered in with cricket chirps, Afro-Brazilian candomblé drumming, an exotic bird call, a glissando of bells, and then a Graceland-era throwback guitar riff, “The Coast” follows a family of musicians that serendipitously communes at a church of St. Cecilia, the patron saint of musicians. The lyrics are opaque — a tad glib — but the family is saved from a lonely life with “sorrows everywhere you turn” by Christ, though, reading between the lines, the musical clan may have gained the trust of the parish through its instruments and joined the service as a solemn obligation. Either way, this is one of those Simon songs where it’s not worth ruminating on the words as much as the feeling it evokes. The music counts among its chipper sounds the return of Ladysmith Black Mambazo, a horn section, a synthesizer solo, and the guitar of Cameroon native Vincent Nguini, who shares a rare co-songwriter credit with Simon.


"Was A Sunny Day" (from There Goes Rhymin' Simon, 1973)

The bass heavy, reggae-inflected “Was A Sunny Day” is a carefree, bouncing tune. The lyrics are cartoonish, but not everything in Simon’s oeuvre has to be as self-serious as “The Sound Of Silence.” Here, he sounds happy to harmonize with Maggie and Terre Roche, two of the three Roche sisters who he discovered and would later produce. On the sunny day in question, there’s nary a cloud in the sky and “not a negative word was heard.” The crystalline weather clearly matches the song’s rocksteady beat and unfettered and alive vibe. The blog Every Single Paul Simon Song claims“Was A Sunny Day” was created using the leftovers of the song that eventually became “Mother And Child Reunion.” There is a dour note hidden in the former, but it shines like fool’s gold. Its disappointment is nowhere as obvious as the bereft feelings expressed in the latter. This is more like a golden ticket with no strings attached: a trip inside a wonderful world.


"Still Crazy After All These Years" (from Still Crazy After All These Years, 1975)

Dominated by a plodding Fender Rhodes line that’s always airy, never bogged down by how many chords Simon has written into this thing, “Still Crazy After All These Years” is the original “Same Old Lang Syne.” By which I mean it tackled the nostalgia of bumping into your old lover set to heavy strings and ending in the anticlimactic feeling of saudade years before Dan Fogelberg’s similar song.

“Still Crazy After All These Years” is a phrase that came to Simon while he was in the shower. At the time, circa 1974, Simon would often take long showers, “to wash away the sadness.” His marriage to Peggy Harper was falling apart and songwriting has always been how Simon processed his feelings. “Still Crazy” is not a bitter song; it’s about acceptance. The word crazy in the title, to me, never stung as a pejorative, but is instead more like the crazy of “a wild and crazy guy” — not someone you avoid in the street, but someone to whom you offer a big hug. It’s a heartwarming ballad of love lost, refound, not rekindled, but remembered as just another up and down in a wild and crazy life.


"Me And Julio Down By The Schoolyard" (from Paul Simon, 1972)

“I sat around playing the collected works of Paul Simon on my stereo and feeling sorry for myself,” the writer David B. Feinberg says in Eighty-Sixed, his roman à clef about gay life in New York’s 1980s. Perhaps due to the world-weariness of Simon & Garfunkel’s songs, people often pigeonhole Simon as a dreary dude. This is incorrect, especially on “Me And Julio Down By The Schoolyard,” which Simon himself called “probably the happiest song I ever wrote” in Robert Hillburn’s definitive book Paul Simon: The Life.

The bright guitar playing, the Brazilian cuíca drum laughing like a bird, and the allegro tempo in a major key (and that cheery whistling) all culminate in a good feeling. That is until you take into account the picaresque story of Julio and the unnamed narrator. The duo is ensconced in some untoward situation, though the mystery of what they did is intel Simon claims even he is not privy to. An easy answer would dispel the appeal altogether. Personally, I like to think of the song as a spinoff of the troubled singer in the Everly Brothers’ “Wake Up Little Susie” or an update on “Punky’s Dilemma.” He’s tippy-toeing down there for what? What did the Mama Pajama see? I have my guesses, but I’d rather stay out of trouble.


"St. Judy's Comet" There Goes Rhymin' Simon, 1973)

When Harper Simon was around one-years-old, he would “stay up pretty late into the night,” Paul Simon told a group of children on Sesame Street in 1977. “So I wrote this song,” he continued before finger-picking a fine tune on his guitar. The song, “St. Judy’s Comet,” from There Goes Rhymin’ Simon, is a lullaby addressed to a sleepy boy who Simon implores to lay his body down, a motif in a popular spiritual of roughly the same name, which Simon may have heard revived as a gospel song.

“St. Judy’s Comet” is a sleepy ditty replete with vibraphone and the soft patter of a shaker — the stuff even insomniacs can’t deny has a somnambulant touch. It’s a lovely ode to a stubborn toddler and the warmth of his father’s love for him is palpable. The Muscle Shoals Rhythm Section joins Simon on the song and adds some gravity to keep Simon from floating away. Worth noting is Pete Carr’s electric guitar, which adds a welcome country twang. The relaxed atmosphere even inspires one of Simon’s cheekier lines: After informing us that he’s going to sing the song over and over until Harper dozes off, he adds, “Cause if I can’t sing my boy to sleep/ Well it makes your famous daddy/ Look so dumb.”


"Mother And Child Reunion" (from Paul Simon, 1972)

Many of Simon’s songs are in conversation with his other songs. He’ll often write what feels like a sequel (S&G’s “America” compared to his solo “American Tune”) to a song from earlier in his career. “Mother And Child Reunion,” for instance, is a stab at Jamaican ska, which he unsuccessfully attempted on Simon & Garfunkel’s “Why Don’t You Write Me.” This time, Simon ditched the American session players, grabbed his passport, and went to a Kingston studio where he was the only white man in the room. He kicked off the jam by saying, “Let’s play some ska,” to which the band replied, “We don’t play ska”; the genre had since grown up and into reggae.

“Mother And Child Reunion” is audibly more authentic than its predecessor, from the opening drum roll, through to the percussive upstroke organ playing from Neville Hinds, to the climactic quartet of female singers — including Cissy Houston, Whitney’s mother — swelling around Simon’s voice as he meditates on grief. It’s a sad song in which a father, addressing his child at her mother’s funeral, says he has no false hope to give. But the desperation is belied by the spiritual music, which does offer at least a glimmer of something good to come, someday down the line.


"Peace Like A River" (from Paul Simon, 1972)

Graceland is the most popular Paul Simon album. But the real heads know Paul Simon is his best album. “Peace Like A River,” which appears on side two, is an understated gem. Its title is a reference to the Hebrew Bible. (In Isiah 48:18, God says, “Oh that you had paid attention to my commandments! Then your peace would have been like a river.”) Simon’s song also begins with an exclamation, in his case “Ah,” which he sings across eight beats. The light drum of congas carry the soft song, rounded out with the Wrecking Crew’s Joe Osborne on bass and Simon playing a tuned-down acoustic guitar in a Spanish style with newfound verve.

“Peace Like A River” is about a dream of a new world in which the meek have finally inherited the earth. Simon rouses from the dream and realizes it’s just that, but, he concludes, he feels reconciled. The levity he feels is expressed most readily in the song’s uplifting chorus. Simon sings of having his faith tested, but, no matter. If he’s beaten with wires or chains, he will persist, he declares while harmonizing with a choir of his layered voice. A rare feat for a chorus, it only appears once in the song, making it all the more vital.


"The Late Great Johnny Ace" (from Hearts And Bones, 1983)

Paul Simon has a shallow songwriting toolbox that he uses to construct songs of great depth and pathos. Case in point, “The Late Great Johnny Ace.” It covers many of Simon’s token themes, mainly the loss of innocence and hero worship (“Where have you gone Joe DiMaggio?/ A nation turns its lonely eyes to you”). He does this via a trifecta of Johns killed by gun violence: the titular R&B singer Johnny Ace, John F. Kennedy, and John Lennon.

“Johnny Ace” has three parts: The first is a somber reflection on hearing the news about Ace’s untimely death at age 24, of an accidental self-inflicted gunshot to the head, the second picks up some steam, while the third section, as is traditional in a ternary, retains the theme of the first. The tense bookended sections are sparse: Simon’s vocals are high in the mix and his voice is resonant with melancholia. The middle section flits along like an old rock ‘n’ roll number — featuring dry snare drum and a talking bass line — as Simon covers his time in England with Kathy Chitty and the music (Beatles, Stones) that was in the air in the ’60s. He sounds jubilant, but the ugliness of the string arpeggios creep back in as he details a “cold December evening” when a stranger on the street asks him if he’d heard the news about Lennon’s death. And just when your nerves are raw, a climactic coda, courtesy of Philip Glass, kicks in. The moving one-minute resolution features pulsing strings grounded by clarinet bass and punctuated by a melodic line on the flute. Simon’s songwriting, boiled down, is about finding the happy in the sad. Here, he lingers in the darkness; no revelations in the naked light, just a powerful song that makes you return again and again to its heartening discomfort.


"Duncan" (from Paul Simon, 1972)

In a career filled with great opening lines (“When I think back on all the crap I learned in high school/ It’s a wonder I can think at all”), “Duncan,” the second track on Simon’s self-titled second solo album, is in the upper echelons for its humor and grace. It goes, “Couple in the next room bound to win a prize/ They’ve been going at it all night long.” We’re told this by the song’s narrator, Lincoln Duncan, a man on a journey who recounts his life and first sexual encounter to the tune of acoustic guitar and the sparkling timbre of treble heavy charango arpeggios.

This bildungsroman is arranged simply: Simon dramatizes the narrative with flourishes on his guitar’s lower register, which sounds like a walking bass line, but mostly it’s his words that shine through. Throughout, he’s accompanied by Andean folk group Los Incas, with whom he had previously worked on “El Condor Pasa (If I Could).” Between verses, the band plays two flutes in harmony, which act as the hook and give this wandering epic a sense of home.

Simon, who is self-conscious of his voice, gives an elevated performance on “Duncan.” There are about half a dozen moments worth pausing over. For instance, the way he repeats phrases and plays with syllables, stretching them for maximum effect, like when sings the word survival, as sur-vy-ee-ay-ee-ay-ee-eye-val. You’d be hard pressed not to find that vivifying.


"Graceland" (from Graceland, 1986)

Paul Simon, one of the greatest singer-songwriters of the 20th century, notices things, like the way his ex-wife Carrie Fisher brushes her hair from her forehead. He sings about it on the apotheosis of his talents, the title track to 1986’s Graceland, and, as a result of being an astute observer, he finds it insulting when she suggests that she’s leaving him. It causes him to shift his tone. He’s wounded (“Losing love is like a window in your heart/ Everybody sees you’re blown apart” *oof*) and the hurt is no longer contained when he emphasizes the words, “As if I didn’t know that” before acquiescing into his easy, nasal tone — with its faint registration of a Queens accent — and he completes the couplet with “As if I didn’t know my own bed.” The song builds toward that moment, but it’s so much more than just that snippet. It’s a song about salvation. It’s a song about America. It’s a song about the death of one thing and the phoenix-like rebirth from its own ashes.

“Graceland” opens with a drum-roll then a fretless bass riff that comes on like a car shifting into gear. We’re off. The listener is his nine-year-old son sitting in the passenger seat as the Mississippi River flies by in the window. It breathes; it takes its time before Simon begins singing. A pedal steel guitar, which adds a rockabilly flavor, comes in with mellifluous playing courtesy of Ray Phiri.

The genre is worldbeat, with its South African percussion, which is not quite on the three and four, but instead straddles either side of the three, not out of sync but unique. Simon built the song around Vusi Khumalo’s drums. The Everly Brothers are thrown into the mix, singing harmonies with Simon. (There’s a great clip from the Classic Album series where Simon plays back their isolated vocals; “Too many words for them,” is his response.)

Simon and the South African musicians influenced each other in equal measure. During the session, Phiri played an E chord, an A, and then a C-sharp minor, which surprised Simon. In South African music, they don’t ordinarily play minor chords. Phiri said he listened to Simon’s records and Simon used the chord all the time. It’s the quality in the song that makes going to Graceland a pensive pilgrimage. The minor chord adds a reflective quality to the song’s celebratory, upbeat rhythm.

Simon never went to Graceland with his son; however, the song itself is a journey, a “shot at redemption” as another song on the album puts it. He doesn’t know why he’s going, but he does believe he’ll be received. He’s resting his fate on a religious sense of faith, like he did when he controversially cut an album in South Africa. It paid off. South African music went global and Simon wrote the best song of his career.

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