When Paul Simon announced his retirement from touring, he was clear about his intended pursuits in his autumn years: Spirituality, neuroscience and the occasional one-off gig benefiting the environment. (Ideally in "acoustically pristine halls," he clarified.)
The latter is a clever way to frame your wind-down: just quitting touring, not all the other stuff. Because it leaves open the possibility for more public music-making. And Simon has taken advantage of that caveat: ever since he plucked his final note on his farewell tour in 2018, he’s played one-offs that laid audiences flat.
Case in point: his brief set to an agog audience at Newport Folk Fest in 2022. As the sun set over the water, he closed with an undeniable classic, which he wrote as a shaken youngster in response to the Kennedy assassination: "The Sound of Silence." This writer was there. You could cut the vibe at Newport with a knife.
The experience drove home how Simon’s songs already reflect his planned post-retirement pursuits. Simon’s written brilliant inquiries into spirituality, like "Questions for the Angels." Countless tunes from "The Sound of Silence" onward deal heavily in psychology. The environment? Check out multiple songs from his most recent album, 2016’s Stranger to Stranger.
All these themes are bound to swirl around "Homeward Bound: A GRAMMY Salute To The Songs Of Paul Simon," a two-hour special set to air on CBS on Wed. Dec. 21 from 9-11:00 p.m. PT/ET. Featuring everyone from Garth Brooks to Angélique Kidjo to Stevie Wonder, the performance will illuminate the 16-time GRAMMY winner's timeless and revered songbook.
A retired Simon may go on to abandon music entirely, but what his songs added to the public consciousness may dwarf anything he could pursue in a scientific or philanthropic sense. Because Simon’s greatest works are some of the finest inquiries into the human experience — internal, external, and ineffable — ever penned.
A 15-song list of the finest Simon tunes could easily, and fairly, fall in line with his greatest hits. But what's the fun in simply reproducing the "essentials" playlists across streaming services? So, if you’ll forgive a lack of "Kodachrome" or "50 Ways to Leave Your Lover," we’ll raise you deep cuts you might not be familiar with. The list is below.
"The Sound of Silence"
In 1963, a 21-year-old Simon softly fingerpicked an acoustic guitar in the reverberating bathroom of his family's Queens home. He had a spectral melody in mind, but the words hadn't come yet.
But when John F. Kennedy was assassinated in November of 1963 — just over a month after Simon's 22nd birthday — a line came to his lips, staggering in its power and simplicity. "Hello, darkness, my old friend," he sang. "I've come to talk with you again."
A meditation on distance between human beings, "The Sound of Silence" unfurls with borderline terrifying, hallucinogenic power — and has lost zero impact across the decades. On the 10th anniversary of the 9/11 terrorist attacks, which occurred a few subway stops from his apartment, he sang it on Ground Zero.
The electrified, pop-friendly version of "The Sound of Silence" is the one everyone knows; riding on the popularity of the Byrds, electric guitar and drums were added in post-production.
The one to truly cherish is the sparse, acoustic version included on the Old Friends boxed set. It’s not on YouTube, but it’s on streaming — and it’ll make the hairs on your arms stand up.
"The Boxer"
From that "darkness" flies an ember of resilience: "The Boxer," from Simon and Garfunkel’s final studio album in 1970, Bridge Over Troubled Water.
"The Boxer" is just as haunted, but in a realistic sense. Instead of depicting phantasmagoric images of blazes of light and prophetic pronouncements, the narrator finds himself unmoored in New York City: "Laying low, seeking out the poorer quarters/ Where the ragged people go."
According to Simon, these feelings stemmed from his battle with the critics: "I think the song was about me," he told Playboy in 1984. "Everybody's beating me up, and I'm telling you now I'm going to go away if you don't stop."
These gloomy verses tip into a wordless lamentation of a chorus, which swells with power after the unforgettable final verse. Therein, Simon sketches a portrait of a pugilist. He’s beaten, weary and humiliated, but unwilling to surrender.
Then, that chorus slams back in, augmented by reverberated cannon-shots from Wrecking Crew drummer Hal Blaine. Right then, from hopelessness springs courage. "Lie-a-lie." Crash.
"Bridge Over Troubled Water"
That voice. No, we’re not talking about Simon’s, as fluid and supple a vocalist he is. Any analysis of Simon and Garfunkel’s music must acknowledge Art Garfunkel’s world-beating talent as a vocalist, and his creative synergy with his more celebrated former partner.
"Bridge Over Troubled Water" began as a demo by Simon; in the studio, it took on wonderfully grandiose dimensions.
From Garfunkel’s mostly unaccompanied lungs — although Simon sings a harmony near the end — this devotional testifies like gospel and surges like an orchestra.
However you feel about the somewhat controversial, belatedly added third verse, "Bridge Over Troubled Water" is a masterpiece in a songbook full of them.
At the 1971 GRAMMYs, the song won a golden gramophone for Record Of The Year; the album of the same name won a GRAMMY for Album Of The Year.
"America"
Come 1968, America was in flux — Vietnam, MLK, RFK. And few songs released that year channeled all that turmoil, uncertainty and abstraction into such a Möbius strip of a song.
Listening today, as the country reckons with the sins of its past and questions the circumstances of its own founding, the America in "America" feels like this one.
Simon’s itinerant protagonists set out to discover this nebulous concept for themselves, yet the song finds no resolution. Still, the aching melody and indelible chorus will imprint themselves on your memory.
"America" is another example of a Simon tune that finds the light just as it can’t feel darker: "‘Kathy, I'm lost’, I said, though I knew she was sleeping," one character reports. "I'm empty and aching and I don't know why."
And in the sea of cars on the New Jersey Turnpike, Simon finds totality, oneness, and a paradoxical sense of peace. What is America? All of this, and none of this. It’s the search that’s so damned satisfying.
"Mother and Child Reunion"
In 2022, before Simon’s unannounced Newport Folk appearance, Nathaniel Rateliff and the Night Sweats performed an exultant set of Simon covers — beginning with "Mother and Child Reunion," that effervescent classic from his self-titled 1972 album.
It was a long, dusty, sweltering day for this writer — one where it was tempting to call it. But the decision to stick it out paid off.
As soon as Rateliff and his accompanists launched into "Mother and Child Reunion," every inch of exhaustion melted away; it felt physically impossible to not holler along.
Simon caught the inspiration to write the tune from the name of a chicken-and-egg dish on a Chinese restaurant menu; the reggae-inflected sound is all Jamaica, reflecting its recording in Kingston.
The result could wrest you from a bedridden depression; "Mother and Child Reunion" is pure release, relief, and exaltation. Word to the wise: reach for it in the darkness.
"American Tune"
1973’s There Goes Rhymin’ Simon is chock full of classics, like "Kodachrome," "Take Me to the Mardi Gras," "One Man’s Ceiling is Another Man’s Floor," and "Loves Me Like a Rock." But the arguable centerpiece is "American Tune" — essentially "America" in concept, but several degrees deeper and more philosophical.
Simon wrote it right after Richard Nixon was elected. It reflects the complication of that moment, cycling through a multitude of chords as if it’s turning each one over like a leaf and pondering it.
"We come on the ship they call the Mayflower/ We come on the ship that sailed the moon," Simon sings at its crescendo, as the strings swell to a head. "We come in the age's most uncertain hours/ And sing an American tune."
While still early in his career, Simon had written not one, but two alternative national anthems — ones that got beneath the hood and truly examined the oppression, jubilation, and complication that makes this place tick.
With such an economy of language, to boot. And although he rarely got this political again, in a way, he’d just keep writing more.
"Hearts and Bones"
1983’s subtle, supple Hearts and Bones typically gets lost in the Simon conversation, as the titanic Graceland would follow it three years later. But the title song alone is worth the price of admission.
What immediately jumps out about "Hearts and Bones" is Simon’s elegant verbiage, charged with erotic energy: "The arc of a love affair/ His hands rolling down her hair/ Love like lightning shaking ‘til it moans." But the song is so effortlessly percolating, so smooth and rolling, that it’s easy to let the details fly over your head.
The lovers are "one-and-a-half wandering Jews" roving through the Sangre de Christo mountains in New Mexico. The second verse is a flashback to nuptials: "The act was outrageous/ The bride was contagious/ She burned like a bride."
Finally, the sojourners return to their "natural coasts" to lick their wounds and "speculate who had been damaged the most."
Who could the itinerant couple be? None other than Simon and Carrie Fisher. (The late Fisher was the half-gentile.) These layers of details give "Hearts and Bones" astonishing gravitas: Simon himself has considered it to be superior to "The Sound of Silence."
"As the writing gets more complex and more layered, it's harder to have a lot of people who really like it," Simon admitted in a 1986 interview. Now that the dust has settled, it’s time to give this astonishing song its due.
"Graceland"
By the time Simon was ready to make a career-defining statement in Graceland, his writerly voice had become maximum-cerebral; Simon was writing about distances and journeys and potential reunions with astonishing detail and verve.
And it all came to a head with "Graceland" — his self-described "true hybrid of South African music and American." Therein, drummer Vusi Khumalo choogles like Sun Records; fretless bassist Bakithi Kumalo adds buoyant swoops; rock ‘n’ roll progenitors the Everly Brothers coo along.
What follows is nothing short of a songwriting clinic. "Graceland" isn’t about Graceland at all; as Simon has explained, it’s about the journey, not the destination.
Nine words capture Simon’s surroundings: "The Mississippi Delta was shining like a national guitar." His failed marriage to Fisher hangs heavily in the air. The incisive chorus details how a shattered heart renders us all see-through.
Ever notice the songwriting trick behind the line about "the girl in New York City who calls herself the human trampoline"? He doesn’t bother to give her a name or a motive, or any further detail at all; it doesn’t matter.
Because she could be anyone in our lives, teaching us to fall, fly, and tumble in turmoil. We all rub shoulders with ghosts and empties. Graceland is any promised land, just out of our reach.
But, know this: we all will be received.
"Diamonds on the Soles of Her Shoes"
Before opening up into its mellower latter half, Graceland builds to a fever-pitch of momentum and anticipation that’s borderline absurd.
In the opening, vocal group Ladysmith Black Mombazo backs Simon in Zulu chordal harmony, roughly translating to "It’s not usual but in our days we see those things happen. They are women, they can take care of themselves."
Then, that irresistible groove, with Simon’s conversational yet hyper-melodic diction. The storyline itself, exploring love amid class differences, is rendered a dreamlike blur.
Still, the key lines cut to the quick: "She was physically forgotten, but then she slipped into my pocket with my car keys." Who with a pulse hasn’t experienced this sensation, never quite given a name, or expressed in the English language so succinctly, until then?
Even when it’s difficult to parse Simon’s literal meaning ("She makes the sign of a teaspoon/ He makes the sign of a wave"), his verbiage is gorgeous. And by the time the economical clash of lovers ends up "sleeping in a doorway" uptown, the song detonates like fireworks, in a jubilant rain of scatting.
"You Can Call Me Al"
Aurally, it’s difficult to think of another song in the pop canon quite like "You Can Call Me Al." Synth-horn fanfare, bubbly polyrhythms, massive gated reverb on the snare, a reversed bass solo, a friggin’ pennywhistle solo: were these elements ever combined to this effect?
Then, there’s the laconic Simon, way behind the beat, effortlessly fitting busy verses into the groove like a rapper, images spinning in infinity. A disillusioned, middle-aged man in a foreign land laments his lack of purpose, snaps at strangers, and vapidly whines for a "photo opportunity."
Even as the music leaps and bounds, Simon’s character’s dark night of the soul reaches a head — his "role model" has fallen from grace, embroiled in some scandal with a "roly-poly bat-faced girl."
But as the culture-shocked protagonist wanders through what we might have called the "third world" in 1986, he finds something like salvation, or grace. The "angels in the architecture" swirl into a celestial portal; the song becomes William Blake-sized.
As "You Can Call Me Al" crescendos, confetti practically rains from the ceiling. When Simon sang it on the final night of his farewell tour, Forest Hills Stadium went up. From lyrics to melody to production to the classic video starring Chevy Chase, this is a bona fide ‘80s classic.
"The Coast"
Juiced up from Graceland’s blockbuster success (despite poorly-thought-out apartheid controversy), Simon continued in a so-called "worldbeat" direction with 1990’s The Rhythm of the Saints.
Despite being far less splashy than Graceland and lacking a hit single, The Rhythm of the Saints is just about perfect. With synthesizers excised, it achieves a naturalistic quality that its predecessor lacked, and songs like "The Obvious Child," "Can’t Run But" and "The Cool, Cool River" rank among his very best.
For whatever reason, the magnificent "The Coast" tends to get lost in the shuffle — and it shouldn’t be. From a dust-devil of hand-drums and windchimes, it coalesces in the air; it feels weightless, continually ascending, never reaching a ceiling.
In the chorus, Simon undercuts an everyman lamentation — "This is a lonely life/ Sorrows everywhere you turn" — with an oblique hustler’s inner monologue: "That is worth some money, if you think about it!"
Always with a way with a finale: as backing vocalists join the throng, Simon sings of stars and skies falling across the shore; the drums shimmer in the air like fireflies. Graceland was pop magic; "The Coast" is just magic.
"That’s Where I Belong"
2000's You’re the One is rarely brought up outside of the most zealous Simonite circles, but Simon clearly thinks a lot of it: he included a whopping four of its songs on his 2018 album of deep-cut re-recordings, 2018's In the Blue Light.
The original album’s opener, "That’s Where I Belong," isn’t among them. But the obscure track, in its own quiet way, a treasure.
Every element of "That’s Where I Belong" exudes a sense of peace Simon hadn’t fully touched on before. Simon said in an interview at the time that "It’s the first time I ever had domestic bliss," and the entirety of You’re the One is charged with that energy. And everything about "That’s Where I Belong" feels enveloping, capacious, invitational — a balm and a hideaway.
At the end, he sings of a villager — a "spiny little island man" at the mouth of a river, with music in the air. That, Simon sings, is home.
"Darling Lorraine"
"I always thought ‘Darling Lorraine’ was one of my best songs," Simon told Mojo in 2018, which galvanized him to give it a fresh coat of paint on In the Blue Light with accompanists like guitarist Bill Frisell, bassist Renaud Garcia-Fons and drummer Steve Gadd.
Unlike many of the above songs, "Darling Lorraine" doesn’t build to a climax; it hesitates, pontificates and mulls for its seven-minute runtime. This is appropriate for the subject matter: Simon negotiates the hills and valleys of a turbulent marriage — and no relationship is a completely neat arc.
The couple are a mismatch. The husband, Frank, is uptight and reticent, and gave up a dream of a musician life; Lorraine is effervescent and open-minded. Naturally, she feels stifled by domesticity; the song captures their arguments and walk-outs. Finally, she dies bedridden, "her breathing like the echo of our love."
Simon’s choice of including "Darling Lorraine" with the equally obscure You’re the One cut "Love" is interesting. That song pulls apart the four-letter concept like a child examining the guts of a radio; "Darling Lorraine" is love in action, seemingly unspooling in real time, and eventually being extinguished.
And even after "the moon takes Darling Lorraine," the song seems to hang in the air, like a faint plume of smoke.
"Wartime Prayers"
Simon’s Eno-assisted album Surprise may have been released in 2006, during the height of the Iraq war. But this is Simon we’re talking about, he would never write his own "Freedom" or "Let’s Impeach the President."
Instead, Simon analyzes the efficacy of prayer. What does it mean to appeal to the Most High during peacetime? How do rice Christians and religious hypocrites add static to the connection?
Ultimately, Simon seems to concede that "wrapping yourself in prayer" can be the final tool in the toolbox when dealing with suffering and death. Crucially, he never preaches: "I don't pretend that I'm a mastermind/ With a genius marketing plan."
Rather, Simon wonders how much he can sand his rough edges and embrace grace before the end of his life. At a time when death and uncertainty hung in the air, "Wartime Prayers" rang true.
Of all the Bush-era songs by classic rockers, this one arguably reverberates strongest — right up to our days of bloodshed in Ukraine, 14 years later.
"Questions for the Angels"
In 2018’s Paul Simon: The Life, Simon laid out his spiritual MO.
"If there is a God, and He created this planet and everything on it, I’ve got to say an incredible ‘Thank you so much — great job,’" he stated. "If it turns out there’s no God, I still feel the same way. I’m really grateful to be here. What a beautiful planet."
Seven years earlier, mortality was on Simon’s mind; it weighs heavily on his 2011 album So Beautiful or So What. On "The Afterlife," he envisaged heaven as a mind-numbing bureaucracy akin to the DMV. He followed that thread deep into the album, and the result is "Questions for the Angels."
It’s a song of riddles and reflections on materialism, following a modern-day pilgrim as he traverses New York "at the hour when the homeless move their cardboard blankets / And the new day begins." The character walks across the Brooklyn bridge and looks at a billboard of Jay-Z.
Everything about "Questions for the Angels" feels primeval; Simon wants to know about the animal kingdom, the state of his mind and the nature of divine connection. Hey, that sounds like Simon’s post-retirement plans — dealing in psychology, spirituality, ecology.
"Somewhere, in a burst of glory/ Sound becomes a song," Simon sang at the outset of "That’s Where I Belong." Maybe he’s ready to write the third part of that life. His songs are about to become him.
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