Paul Simon felt grateful.

It was March 2001, and the occasion was the 16th-annual Rock and Roll Hall of Fame induction ceremony, held at the Waldorf Astoria in midtown Manhattan. Along with another honoree that night, Michael Jackson, Simon joined an elite group of artists that has been inducted multiple times. In 1990, he entered the hall as part of Simon & Garfunkel, a dysfunctional but immensely successful musical marriage with Simon’s childhood friend and eventual adversary, Artie. (Simon had been eligible for induction as a solo artist since 1991.) By the time he released his first post–Simon & Garfunkel solo LP in 1972, Simon had already written a career’s worth of iconic songs: “The Sound of Silence,” “I Am a Rock,” “Homeward Bound,” “Mrs. Robinson,” “America,” “Bridge Over Troubled Water,” and many more. He was also incredibly rich, due to owning his own publishing. Practically all of Simon’s classic-rock colleagues — including Bob Dylan, the Beatles, and the Rolling Stones — spent millions in the late ’60s and early ’70s untangling themselves from onerous business deals. But Simon had come up as a teenager in the streetwise world of New York indie labels and publishers — many of them housed in the world-famous Brill Building — working as a song plugger, session guitarist, and budding composer, penning dozens of terrible would-be teenybopper hits like “Teenage Fool” and “Get Up & Do the Wobble.” He was savvy about the value of songs and protecting a hard-won artistic persona. Both had served him well.

In spite of a cocksure aloofness that rubbed many of his contemporaries the wrong way — John Lennon once supposedly referred to the 5-foot-3 Simon as “the singing dwarf” — Simon was often beset by writer’s block and other crises of confidence. After Simon & Garfunkel’s 1970 swan song, Bridge Over Troubled Water, won Album of the Year at the 1971 Grammys (beating out other soothing singer-songwriter benchmarks like Déjà Vu by Crosby, Stills, Nash & Young and Sweet Baby James by James Taylor), Simon spent 10 months fretting over his self-titled solo LP, all the while convinced that many in the music industry were betting on the lanky, blond, and angelic-looking Garfunkel having the better solo career. Even after Paul Simon sold more than 1 million copies and spawned two of his most famous tracks, the reggae-infused “Mother and Child Reunion” and the delectable Latin pop number “Me and Julio Down by the Schoolyard” — as well as one of his most beloved deep cuts, the evocative story song “Duncan” — Simon’s self-doubt persisted.

Perhaps this was on his mind as Simon strode to the podium dressed in his usual business-casual attire — white sports jacket, black T-shirt, and red ball cap pulled down tight over a balding dome — like an aging talk show host warming up the audience a few minutes before airtime. Unfortunately, video of Simon’s speech isn’t available online; the Rock Hall induction ceremony back then wasn’t the arena-based spectacle that it is now. (Look closely and you can see Simon playing “Julio” with Jann Wenner on backing vocals during the night’s de rigueur climactic jam session.) But according to accounts of the evening, Simon gave one of the longest speeches in the ceremony’s history, setting an unofficial record by thanking 50 people.

He acknowledged ’50s rock and roll disc jockey Alan Freed, who played Simon’s first hit with Garfunkel, 1957’s “Hey Schoolgirl,” recorded under the name Tom & Jerry, when Simon was just 15. He expressed gratitude for the fans, including “those two girls in Covington, Kentucky,” for undisclosed reasons. He even gave a shout-out to frequent sparring partner Garfunkel, expressing remorse for “the ending of our friendship” and hope that “one day before we die, we will make peace with each other.” Simon and Garfunkel would make peace after that, and then fall back into discord. In 2015, Garfunkel called Simon a “monster” with a Napoleon complex.

Did the appreciation Simon expressed stem from his decisive victory over Garfunkel in the solo-career wars? Or was he feeling reflective over the many twists and turns his life had taken?

Simon’s singular career, which will apparently conclude later this year in New York City at the end of a farewell tour wrapping a few weeks before his 77th birthday, spans more than 60 years, from the dawn of rock ’n’ roll to the Spotify era. For almost that entire run, he’s been a major figure in popular music. His first hit, “The Sound of Silence,” topped the charts in 1966; his most recent album, Stranger to Stranger, debuted in the top three in 2016. Even his old hits have a way of coming back — Disturbed’s gloom-metal 2015 cover of “The Sound of Silence” has sold more than 1.5 million downloads, and been streamed more than 370 million times on YouTube.

Simon was nominated for Album of the Year at the Grammys in the ’60s, ’70s, ’80s, ’90s, and ’00s, a testament to his incredible commercial and artistic longevity. (He won three times, for Bridge Over Troubled Water, 1975’s Still Crazy After All These Years, and 1986’s Graceland.) He even had a long and complicated coupling with Princess Leia, the surest sign of all that he is a master of the universe.

But Simon and Carrie Fisher eventually split in the late ’80s, the second of his failed marriages. (He’s been married to his third wife, the folk singer Edie Brickell, since 1992.) And he suffered humiliating professional setbacks that many blamed on Simon’s hubris, including the 1980 box office bomb One-Trick Pony — which Simon wrote and starred in — and the disastrous 1997 Broadway production The Capeman, a musical about convicted killer Salvador Agron overseen by Simon and a cadre of cronies who flaunted their New York theater inexperience until it led them to artistic and financial ruin, inspiring widespread schadenfreude.

A true show-business lifer, Simon always managed to come back — with his signature achievement, the cross-cultural and intergenerational sensation Graceland, in the mid-’80s, and his unlikely renaissance as a darling of indie rockers in the ’10s. But he’s never been able to shed his enemies.

Even now, among younger generations that learned about his music from family car trips, Wes Anderson soundtracks, and Vampire Weekend albums, Paul Simon and Graceland are flashpoints in an ongoing debate about colonialism and cultural appropriation. Most damning of all are the bevy of accusations from less-famous collaborators, during Graceland but also from decades earlier, who say that Simon lifted their ideas without giving proper credit, or a share of his precious publishing royalties.

As Simon walked up to give his Rock Hall speech, “the applause was polite, the cheers measured, the sound of respect, as opposed to a rush of affection,” biographer Peter Ames Carlin writes in 2016’s Homeward Bound: The Life of Paul Simon. “Was it the lingering effects of the Graceland controversies weighing down their hands? The reports of back-alley tactics used to snatch up what his collaborators, and many others, assumed was theirs?”

It’s a scenario that recalls one of Simon’s most popular songs, “You Can Call Me Al,” from Graceland. Over a deceptively bouncy beat, Simon describes a full-blown mid-life crisis, with the narrator wondering whether after all this time he truly is alone in the world.

When Simon looked out at the audience that night, did he really see a mix of friends, enemies, well-wishers, and rivals, all giving him his due with varying degrees of reluctance? Or was he a man lost in his own songs, seeing angels in the architecture, spinning in infinity? What could he say except “amen” and “hallelujah”?

With the Homeward Bound tour set to open next week in Vancouver, all that’s left for Paul Simon to ponder is his legacy. Let’s start with the songs. Like that other show-biz avatar of 20th-century New York male Jewishness, Woody Allen, Simon specializes in witty tragedies about characters with sophisticated airs. They attend parties hosted by cinematographers and have philosophical daydreams about Jay-Z, but they ultimately fail to live up to the people they imagined one day becoming.

The rueful protagonist of “Something So Right” who likens his emotional distance to the Great Wall of China — that’s the quintessential Paul Simon hero. Boys in bubbles populate his songs. The lonely man in “Still Crazy After All These Years” whose anxieties are triggered by a late-night encounter with an ex-girlfriend. The absentee father in “Slip Slidin’ Away” who kisses his son as he lies sleeping before leaving him again. The departing spouse in “Hearts and Bones” who’s asked by a former lover why he can’t accept her for who she is, and replies, “’Cause that’s not the way the world is, baby.” (“What a great writer,” raved Carrie Fisher, the song’s subject, about that particular lyric.) In possibly his very greatest song, a middle-aged divorcée goes on a road trip to find himself and winds up at the former home of his dead boyhood hero, a metaphor for the afterlife, creative rebirth, rock ’n’ roll fatalism, and the cheap transience of iconic status.

But lyrics are only half the story with Simon. “Just give me some tenderness / beneath your honesty,” Simon sang in 1973 — his music is what delivers that benevolence.

Outside of the Beatles, ’70s Stevie Wonder, ’80s Michael Jackson, and early ’00s Outkast, Paul Simon songs are the easiest to like in the entire modern pop canon. It’s not just that they’re effortlessly melodic and performed by uniformly excellent musicians. There’s an effervescent lightness to his records, no matter the essentially adult nature of the lyrics. Simon doesn’t brood or obscure his hooks behind inscrutable, audio verité–style production like Dylan, Neil Young, or Tom Waits. He prides himself on clarity, musicianship, and a kind of straight-forward sonic sumptuousness. The pop instincts bred into him at an impressionable age when he was a young, hungry striver in the late ’50s and early ’60s never left him, even after punk and new wave spooked (or motivated) his peers.

“Pop music is in a terrible state right now,” Simon complained to Newsweek in 1975. “The staple of American popular music is all three- or four-chord, country or rock oriented now. There’s nothing that goes back to the richest, most original form of American popular music — Broadway and Tin Pan Alley — in which sophisticated lyrics are matched by sophisticated melodies.”

While he’s more musically accomplished than many of his singer-songwriter colleagues, Simon’s songs are rarely as challenging. On the contrary, he bends over backward to engage the listener, painstakingly crafting sounds that seduce the ear and soothe the soul. In the wake of 9/11, it was Simon’s songs about broken individuals grasping for redemption that people turned to for comfort and relief. And Simon seized the moment, knowing intuitively what people needed to hear. When best friend Lorne Michaels asked Simon to perform on the first Saturday Night Live after the World Trade Center fell, Michaels wanted him to play the expected plea for deliverance, “Bridge Over Troubled Water.” Simon instead performed “The Boxer,” a less passive song about taking your lumps and punching back.

Pretty tough for a guy whom critics in the ’70s wrote off as a wimp. But Simon’s lightness served his songs better as he aged. When he started writing in the 21st century about his own mortality, he didn’t emulate Dylan’s bluesy recriminations or Leonard Cohen’s doom-laden whispers, the standards for late-stage “death bed” rock. Instead, he leaned on dry humor and airy melodies that were improbably strong bulwarks against primal fear of the big empty. It helps that, unlike Dylan, Simon still sounds like himself. On Stranger to Stranger, his sweet, boyish tenor retains the conversational fluidity of a man uttering spontaneous confessions over morning coffee.

In the process, contemporary music critics — who can be hostile to white, male, boomer rock icons — have come around on Simon in a big way. Simon’s rejection of old-fashioned rockist machismo made him a target 40 years ago, when he was viewed as a soft-rock dweeb with zero outsider cred. But today, Simon’s willingness to veer beyond conventional, folk-based “three chords and the truth”–style songwriting seems strikingly contemporary. Even the curatorial role he adopted on Graceland, in which he built tracks from cherry-picked riffs and rhythms created by South African musicians, has been likened to modern production techniques. If you love My Beautiful Dark Twisted Fantasy, in which Kanye West played maestro to an army of talented contributors in Hawaii, is it possible to see Graceland in a new light?

“No matter what Simon listens to, he hears nothing but raw ingredients for Paul Simon songs,” observed The New Yorker’s Kelefa Sanneh in 2016. “When he finds something he likes, he makes it his own, on the correct assumption that most people will enjoy it too much to complain.”

It’s funny how times change — I suspect that at least a few people gathered at the Waldorf Astoria for the Rock Hall induction in 2001 merely looked at Simon as a thief.

Carlin’s book revisits the people who have accused Simon of musical larceny over the years. There’s Martin Carthy, a legendary British folk guitarist who passed along some fingerpicking techniques to Simon when he was living in England in the early ’60s, along with the arrangement of “Scarborough Fair” that Simon & Garfunkel made famous in The Graduate a few years later. Carthy grumbled that Simon was a scoundrel, though Simon later claimed that the royalties he had forwarded to Carthy’s publishing company hadn’t been passed on to the guitarist. More than 30 years later, when Simon finally learned about the mistake, he made Carthy whole again, which apparently satisfied Carthy enough for him to forgive the transgression.

When Simon traveled to Alabama in 1972 to record several tracks with the house band at Muscle Shoals Sound Studio, known as the Swampers, for There Goes Rhymin’ Simon, keyboardist Barry Beckett felt that he had written the descending piano riff that opens and closes “One Man’s Ceiling Is Another Man’s Floor.” But Beckett didn’t press the issue — Simon gave the band members coproducer credits on the Muscle Shoals tracks, and paid well above scale for the sessions, as is Simon’s custom. Besides, there was also the code of the studio musician, which is anyone who haggles over songwriting credits ought to make their own damn record.

The complaints from disgruntled musicians that came out of the Graceland sessions have been the most persistent. Simon shares songwriting credits on five tracks — “The Boy in the Bubble,” “I Know What I Know,” “Gumboots,” “Diamonds on the Soles of Her Shoes,” and “Homeless” — all of which were made in collaboration with South African players. But the album’s two concluding songs, “That Was Your Mother” and “All Around the World or the Myth of the Fingerprints,” came out of sessions with Americans: the Louisiana zydeco band Good Rockin’ Dopsie and the Twisters and the great Los Angeles rock group Los Lobos, respectively. Both bands claimed that Simon took their music and wrote lyrics and melodies on top of it without sharing songwriting credits.

And then there’s Heidi Berg, a young guitarist who met Simon via Lorne Michaels, her former boss at SNL and the short-lived The New Show. Berg, who wanted Simon to produce her debut album, loaned him a tape of South African music called Gumboots: Accordion Jive Hits, Volume II. Berg envisioned a record that integrated elements of the music on that tape with her own songs, particularly the boisterous accordion sound from “Gumboots,” a regional hit for a mbaqanga trio called the Boyoyo Boys. She assumed that stateside studio musicians would replicate it for her record.

“Why don’t you go to South Africa and record with the people who made the original records?” Simon asked, as Berg recalls in Carlin’s book.

Berg could only laugh. She didn’t have the means to go to South Africa, track down all of the musicians, and set up studio time.

But Paul Simon did.

“I thought seriously about writing my own memoir,” Simon announced in 2014, “but I’d rather devote my time to making music, which continues to hold my full attention.” So he gave his blessing to former Los Angeles Times music critic Robert Hilburn to write Paul Simon: The Life, which arrived this week.

Reading Hilburn’s book, I sometimes forgot that it wasn’t a memoir. While Hilburn interviews a sizable cast of friends, family members, collaborators, ex-wives, and muses — including normally reticent subjects like Simon’s first wife, Peggy Harper, and his ’60s-era girlfriend, Kathy Chitty, who inspired many of Simon & Garfunkel’s loveliest tunes — Simon’s point of view dominates The Life.

The book certainly feels like a memoir, in that Simon seems primarily concerned with settling scores and disputing the most unflattering things ever written about him, particularly Carlin’s book. (Simon was “remarkably hostile” to Carlin’s project, the author has said.) Hilburn, meanwhile, happily cedes the floor to Simon. According to The Life, Simon never slept with groupies or used any drug stronger than a brief dalliance with ayahuasca in the late ’90s. When Simon swiftly explains away the stories about him ripping off his backing musicians, Hilburn’s only counter is to quote Simon’s friends testifying to his generosity with studio wages and inclusivity in the liner notes. (He notes that the credits for 1990’s lavish, often brilliant Graceland sequel, The Rhythm of the Saints — which employed around 100 musicians from around the world — runs “as long as the scroll of names at the end of a movie.”) Whenever Hilburn must delve into the ugly parts of Simon’s personal life for the sake of the narrative — like the case in which Simon was charged with misdemeanor disorderly conduct after a dispute with Brickell that was quickly dropped in 2014 — you can practically feel his squeamishness and subsequent relief when Simon refuses to discuss any of it in detail.

Hilburn also declines to wade deeply into Simon’s long, strange relationship with Garfunkel. “Paul remembers first seeing Garfunkel in 1951 at an assembly at PS 164 when they were both in fourth grade,” he writes. “Artie, as Paul grew to call him, sang ‘Too Young,’ a ballad that had been a hit for Nat ‘King’ Cole, and Paul was struck by two things: the loveliness of Art’s voice and the strong impression he had on the girls.”

Simon and Garfunkel first performed together in a sixth-grade production of Alice in Wonderland, and not long after Simon wrote his first song, “The Girl for Me,” for them to perform as a duo. But after they received some notoriety as Tom & Jerry in the late ’50s, Simon negotiated a side deal with their record label to put out his own single under the name True Taylor. This “betrayal” by Simon marked the first fissure in his relationship with Garfunkel, who brought it up time and again for decades afterward. Tom & Jerry eventually broke up, and Simon and Garfunkel didn’t reconnect for several years.

The dynamic between the short, insecure, and prodigiously talented Simon and the tall, confident, and medium-talented Garfunkel seems ripe for armchair psychology. But Hilburn isn’t much interested in exploring the inner lives of his subjects, or even indulging in a little fun-spirited soap-opera gawking. The Life both minimizes Garfunkel’s prominence in Simon’s story and repeatedly puts him in his place. In the first 50 pages alone, Simon disputes Garfunkel’s “Napoleon complex” cheap shot on two different occasions. (Later, Hilburn contrasts the glowing critical response to There Goes Rhymin’ Simon with the mediocre reviews for Garfunkel’s solo debut, 1973’s Angel Clare.) If Simon truly didn’t exert editorial control over The Life, as the promotional materials claim, perhaps it’s because Hilburn was already inclined to be deferential.

Hilburn’s access to Simon, no matter his aversion to pressing him, still manages to provide a measure of insight into how Simon thinks and operates. Born in Queens on October 13, 1941, Simon was raised by Belle, an elementary school teacher, and Louis, a bandleader who didn’t spare his son criticism of his early musical efforts. Between 1957 and 1964, Simon bounced around the lower rungs of New York’s pop music world, playing guitar for $50 per session and writing and recording unsuccessful singles under a variety of generic pseudonyms, like Jerry Landis and Paul Kane. One of his friends from that period, Carole King, became a major songwriter with her husband, Gerry Goffin, when their song “Will You Love Me Tomorrow” was recorded by the Shirelles and went to no. 1 in 1961, stoking Simon’s competitive spirit.

“I was glad for her, but it was also incredibly frustrating,” Simon admits to Hilburn. “They were making big hits, and I was still trying to get a record deal or just make another demo. I kept asking myself, ‘How did they do that?’”

As an English major at Queens College, he started writing with a more self-conscious poetic bent, studying the freshman lit canon of Robert Frost, Emily Dickinson, and T.S. Eliot. And he began bumming around the folk scene in Greenwich Village, though he felt out of place. He was, in a sense, living a double life, performing topical broadsides like his own civil rights allegory “He Was My Brother” at night while working as a song plugger during the day, hawking pop dreck like “The Peanut Vendor” to the highest bidder. (“I wasn’t a very good salesman,” Simon tells Hilburn.)

Simon hit upon “The Sound of Silence” in the fall of 1963. Unlike every other song he had written up until then, Louis Simon actually liked this one. “He said it was just the kind of song he loved to hear on the jukebox,” Simon proudly told a friend. By now, Simon had reconnected with Garfunkel, and together they were signed to Columbia in 1964 on the strength of “Silence” by Tom Wilson, producer of Bob Dylan’s early records and, a few years later, the earth-shaking The Velvet Underground & Nico. When the duo’s first album, Wednesday Morning, 3 AM, stiffed, Wilson reworked “The Sound of Silence” without Simon’s or Garfunkel’s permission, overdubbing a jangly backing band highly reminiscent of the Byrds’ recent smash, “Mr. Tambourine Man.” Simon hated it, but Simon & Garfunkel had the first of their 15 Top 40 hits, including three no. 1s.

Simon would never again match his prolific pace as a songwriter during this period. In later years, he would either struggle with a surfeit of inspiration, or tinker for years on the same batch of tunes. “Within a five-year period, from 1965 to 1969, I wrote most of my big hits,” he told Alec Baldwin on Here’s the Thing in 2015. “Now I’m much slower.” His credo at the time was: Never set out to write a song by picking a theme; let the music itself lead the way.

“Bridge Over Troubled Water” came to him one night in early 1969 as he sat strumming his guitar and listening to a record by the gospel group the Swan Silvertones. A line from the pre–Civil War spiritual “O Mary Don’t You Weep” stood out: “I’ll be a bridge over deep water, if you trust my name.” Inspired, Simon wrote quickly, capturing the spirit of the song in maybe 20 minutes. It took another hour and a half to finish off the first two verses. “This is better than I usually write,” he thought to himself.

If an algorithm were tasked with writing the greatest song of all time, it would probably produce something along the lines of “Bridge Over Troubled Water.” It has the sound, feel, lyrics, and structure of A Big Song That Matters. It’s actually a little too epic — I’ve always felt the song peaks in the second verse, when Garfunkel sings “… and pain is all around,” the song’s lump-in-your-throat moment. The subsequent “sail on silver girl” verse, which Simon added later, feels anticlimactic.

But who am I to criticize a deathless standard? “Bridge Over Troubled Water” made Simon a heavyweight. There’s nothing in his catalog that’s remotely like it, before or since. It’s a full-on diva anthem from a folk-pop miniaturist. (Aretha Franklin quickly claimed it as her own until the end of time.)

“Bridge Over Troubled Water” was another of those songs that Simon liked to say was gifted from his “imaginary friend,” the muse that Simon attributed to the mysteries of both God and neuroscience. Music itself was like a deity to Simon. A recurring theme in Hilburn’s book, from his interviews with Simon’s boosterish intimates, is that music might very well be the best friend that Simon has, offering companionship and shelter during his lowest points.

Simon himself seems to agree, though he expresses his love for music in a way that unintentionally reveals how he feels about people.

“Ever since I was 13 or 14, songwriting has always been a great place of security and comfort,” he tells Hilburn. “Songwriting never turned around and stabbed me in the back.”

“Bridge Over Troubled Water” the song and Bridge Over Troubled Water the album were Simon & Garfunkel’s greatest triumphs. And the beginning of the end. Garfunkel wanted to be a movie star — his work on Mike Nichols’s Catch-22 delayed progress on the album, annoying Simon to no end — and Simon wanted people to know that he was the sole genius behind all of those big Simon & Garfunkel hits.

“He didn’t want to sing it himself,” Simon complained bitterly about Garfunkel’s association with “Bridge” to Jon Landau in a 1972 Rolling Stone interview. “He couldn’t hear it for himself. He felt I should have done it. And many times I think I’m sorry I didn’t do it. … Many times on a stage, though, when I’d be sitting off to the side and Larry Knechtel would be playing the piano and Artie would be singing ‘Bridge,’ people would stomp and cheer when it was over, and I would think, ‘That’s my song, man. Thank you very much. I wrote that song.’”

A new career required a new sound. Simon dabbled in what would later be classified as “world” music during his Brill Building days, writing a song for the forgotten pop group Tico & the Triumphs called “Wild Flower” that melded Simon’s bedrock ’50s rock influences with Hawaiian lyrics, a synthesis inspired by the recent Tokens hit “The Lion Sleeps Tonight.” More successful were the international accents applied to Bridge Over Troubled Water, most notably “El Condor Pasa (If I Could),” in which Simon wrote English lyrics to music originally composed by Peruvian songwriter Daniel Alomìa Robles in 1913, and later covered by the Andean folk group Los Incas.

Another Bridge track, later released as the B-side of “El Condor Pasa,” was the ska trifle “Why Don’t You Write Me,” which resembles the Beatles’ “Ob-La-Di Ob-La-Da” far more than anything authentically Jamaican. During the long gestation of his 1972 self-titled solo record, Simon became enraptured by Jimmy Cliff’s “Vietnam,” which was every bit as soulful and gritty as “Why Don’t You Write Me” was twee and, well, white.

Simon had to go to Jamaica and work with the musicians who made “Vietnam,” he decided. He called up Leslie Kong, the producer of “Vietnam,” and Kong eagerly offered his assistance, convinced that Simon could help open the American market to Cliff and another Jamaican singer-songwriter, Bob Marley. When Simon arrived in Kingston with producer Roy Halee, he was met by a murderer’s row of Jamaican musicians who had played with Cliff and Toots & the Maytals, including guitarist Hux Brown and drummer Winston Grennan. Simon was thrilled.

“Let’s play some ska!” he implored. But the musicians didn’t play ska. “Well, what do you play?” Simon asked.

“Reggae,” they replied.

“OK,” Simon said, “let’s play reggae.”

Simon didn’t have “Mother and Child Reunion,” fully mapped out yet. He would play guitar lines and encourage the musicians to add their own reggae-style touches, while singing phonetic sounds in the place of wistful lyrics about the death of Simon’s pet dog. He finished the track in New York, adding words and Larry Knechtel’s piano and female backing vocals, including Cissy Houston’s.

The method and feel of “Mother and Child Reunion” point toward Graceland. But first, some other important bullet points: After making his best and most successful ’70s album, There Goes Rhymin’ Simon, Simon won his second Album of the Year Grammy in 1976 for the jazzy singles-bar fantasia Still Crazy After All These Years. When he reemerged four years later with the film and soundtrack album for One-Trick Pony, Simon was pushing 40 and sporting his most robust hairline since the 1950s.

In the film, Simon plays Jonah Levin, a faded ’60s folkie playing out the string in low-rent clubs in the shadow of energetic new wave bands like the B-52’s. Dismissed by Rolling Stone as a “morose little art film,” One-Trick Pony is better than its footnote status suggests, retaining the “sad comedy” feel of his best songs, particularly the scenes in which Simon and his band (played by Simon’s actual sidemen, including drummer Steve Gadd and bassist Tony Levin) banter in the tour van about bad reviews and dead rock stars.

But Simon spent so long making his passion project that by the time One-Trick Pony came and went from theaters it seemed like he’d written his own obituary. Once again feeling timorous about the state of his career, Simon recruited Garfunkel to join him at a massive concert in Central Park that drew half a million nostalgic ’60s true believers, spawning a popular live album and video that subsequently became a staple of PBS pledge drives.

A tour of arenas and stadiums with Garfunkel followed, and a reunion album was put into motion. But Simon decided that his latest songs, many of which were inspired by his relationship woes with Carrie Fisher, were too personal to share with Artie, and he instead made 1983’s Hearts and Bones a Paul Simon record. On the cover, he wears a black sports jacket over a pink and blue polo shirt with a skinny tie around his neck, a half-hearted attempt to update his image for Duran Duran fans. But the album itself is a kind of yuppie-era Blood on the Tracks, just pure heartache. Commercially, it bombed.

Simon blamed the failure of Hearts and Bones on the album’s flat sound. For his next record, he would make sure that he had exciting musical tracks recorded before he focused on finishing off songs, the reverse of how he and most other singer-songwriters normally work. If the tracks were great, Simon reasoned, it would be easier to write songs over them, rather than vice versa.

What happened next has been well documented, and continues to inspire debate. In Johannesburg, Simon played with the mbaqanga and Township Jive bands from Berg’s Accordion Jive tape, making crucial connections with musicians like guitarist Ray Phiri, who became a fixture in Simon’s band for years. (They later fell out, which Phiri attributed to “bad blood” over disputed Graceland songwriting credits. He died in 2017.) Together, they created the spare parts that Simon would use to build so many wonderful tunes.

On paper, Graceland looks like a prequel to Get Out, about a rich, middle-aged, ostensibly liberal white man who preys on black musicians for their eyes and ears, and is then reborn. But music does not exist solely on paper. It also resides in the heart and the hips, and Graceland moves both. It’s an impossible album not to love until you learn its back story. Then it becomes impossible to love without caveats.

The controversy over Simon’s defiance of the antiapartheid boycott isn’t as urgent now as it was in the ’80s, when Simon hired a crisis management firm to help him negotiate the expected media firestorm. (Perhaps that’s why Hilburn’s book doesn’t address the most scandalous Graceland-era charge against Simon, made by Sun City organizer Steven Van Zandt and noted in Carlin’s book and elsewhere, that he dismissed the African National Congress and the imprisoned Nelson Mandela as tools of the communists.) But concerns about cultural appropriation, leveled against Simon at a public forum held at Howard University in early 1987, have only intensified over the years.

“How can you justify taking over this music?” asked Howard sophomore Mark Batson, as Simon felt a mix of discomfort and anger. “For too long, artists have stolen African music. It happened with jazz! You’re telling me the Gershwin story of Africa!” (Batson, now a successful producer and songwriter, later won Grammys in 2010 and 2011 for his work with another famous signifier of cultural appropriation, Eminem.)

Does motivation matter here? Is it possible to ascertain what Simon’s actual motivation was? Simon has said, in Hilburn’s book and elsewhere, that his love of the music drew him to the source. Politics did not matter to him as much as sounds. Just as he traveled to Jamaica to make “Mother and Children Reunion,” he went to Johannesburg to gather the raw materials for Graceland because that’s what he needed to make the best music. The songs, he believed, would justify themselves. This is arrogance, and it’s also the sort of single-minded zeal driving the creation of masterpieces that nourish millions. If Simon had acted appropriately, Graceland probably wouldn’t exist. He bet instead, recklessly and presciently, on great art outlasting bad politics.

My position on Graceland, I suspect, is common. I adore it, and also believe the criticism of it is justified. People will love this album for as long as pop music exists, but they’ll also always be made aware of how it was created. His collaborators will not be erased, nor will they ever get their full due. And this will provoke discussion, as well as dancing. Ultimately, Graceland is a monument, and also a door.

In 2011, I interviewed Paul Simon over the phone for about 20 minutes. He was, as advertised, a little prickly and really insightful. I don’t remember a lot about the conversation — I was in the midst of dealing with a terrible personal crisis when I had to stop to take Simon’s call, a good setup for a Paul Simon song about the extraordinary colliding with daily disappointment.

Based on the published Q&A, Simon pushed back against some of my assertions about his latest record, So Beautiful or So What. Like most critics, I had seized upon the album’s lyrics, which in frisky and shimmery songs like “The Afterlife” and “Questions for the Angels” contemplate the meaning of life with a buoyancy akin to the gospel music that Simon has always loved.

But Simon wasn’t interested in talking about words; he remained enraptured by sound. The Graceland era shift from songwriter to record-maker was still in effect. He raved about working out of his home studio in Connecticut, and how he used decaying bell sounds as a substitute for echo. I pretended like I understood. The kid from Queens spoke like a scientist.

“I probably like to record more than I like to write,” he told me. “I like the abstract more than ‘What does that mean?’ Nobody ever says to you, ‘Why did you use a harmonium?’ Or ‘What is that ringing sound that occurs here?’ The questions are always ‘What does that song mean?’ or ‘What were you trying to say here?’ The abstract is just more interesting because it doesn’t really have anything to say, but if it is good, it creates thoughts and feelings, and I enjoy that.”

The public and critics enjoyed So Beautiful and So What as much as any Simon album in at least 20 years. But Simon was less competitive now. He accepted that he was an outlier who had aged even out of “dad rock”; he was now in cool grandpa territory. His music would no longer have the pop significance that it had in the 20th century. But that didn’t deter him from putting out a new little gem every four or five years.

When Simon read all of those “best since Graceland” reviews for So Beautiful or So What, I wonder whether he felt another impulse to push back, to insist that he had already made his “best since Graceland” album 11 years earlier, with 2000’s You’re the One.

It’s hard to call a record that was nominated for Album of the Year underrated. But You’re the One was up for the award the same year as Kid A, The Marshall Mathers LP, and Midnite Vultures — and lost to Steely Dan’s Two Against Nature — so Simon was written off as one of the category’s stodgy legacy nominations. Simon’s stock was also at its lowest point since Hearts and Bones in the wake of the Capeman debacle. Simon didn’t climb out of that valley by dramatically remaking his music. Instead, he allowed himself to appear humbled, and that humility leavens his funniest album.

I’m sorry, Paul, but your words are still worth quoting. I love this verse from “Old”:

The human race has walked the earth for 2.7 million,

And we estimate the universe at 13–14 billion

When all these numbers tumble into your imagination

Consider that the Lord was there before creation

God is old

We’re not old

The theatrical bent from The Capeman carries over to You’re the One. There’s a trace of Stephen Sondheim in the album’s most remarkable song, “Darling Lorraine,” which documents several decades in the life of a married couple. It’s an uncommonly straightforward narrative for Simon, who dispenses evocative details and crucial plot points with economical grace. It’s the kind of song you can’t talk about without issuing spoiler alerts. Just go listen to it instead.

In the statement announcing his retirement tour, Simon concedes that he may do an “occasional performance in a (hopefully) acoustically pristine hall” for charity. In private, I hope he keeps playing with sounds in his home studio, if only for himself. If he feels inspired, maybe he’ll write one more “Darling Lorraine.” How could he not? Without the songs, what is the point of any of this?

Steven Hyden is the author of two books, including Twilight of the Gods: A Journey to the End of Classic Rock, out now from Dey Street Books. His writing has appeared in The New York Times Magazine, The Washington Post, Billboard, Pitchfork, Rolling Stone, Grantland, The A.V. Club, Slate, and Salon. He is currently the cultural critic at UPROXX and the host of the Celebration Rock podcast.