Paul Simon’s Restless Journey – Rolling Stone
Home Music Music News

Paul Simon’s Restless Journey

How a musical perfectionist from Queens who agonizes over every lyric became one of the most important artists of his generation

Paul Simon

Paul Simon performs in concert in New York City on May 10th, 2011.

Eugene Gologursky/WireImage for New York Post/Getty

LATE AFTERNOON ON A WINTER’S DAY, AND PAUL SIMON IS HARD AT work with his eight-member band in a rented rehearsal studio not far from his home in New Canaan, Connecticut. Simon is preparing the group for a tour of smallish venues in support of So Beautiful or So What, his 11th solo album. Like all his records, So Beautiful is an intricate assembly of tones and chords, and because Simon recorded the 10 songs largely on his own, the band has been gathering to learn them all. Back before 1970, when Simon and Art Garfunkel decided to get themselves free of each other, the two childhood friends from Queens were known as musical perfectionists, so immersed in sounds that they would spend weeks in the studio recording a single new song like The Boxer.” Simon is now near­ly six birthdays past the morning when his old friend Paul Mc­Cartney telephoned to say, “I’m sorry, but this has to be done,” and sang him “When I’m Sixty-Four,” but nothing has changed about his approach to music. Which explains why his percussionist and lead guitarist are currently on their hands and knees, huddled together, ears pressed to a large speaker, trying identify that mysterious tapping noise.

Simon usually comes to rehearsals in a blue, brushed-felt fedora and a hooded sweatshirt, and his public reputation is for being a bit blue and hooded himself. “The only interesting thing is the work,” he says. At the moment, the band is deep into “Rewrite,” a deceptively quiet song on So Beautiful that engages with the intense desire people have to go back and change troubling things that have happened in their past. When he writes, Simon begins with rhythm or melody, and the lyrics come last. Sound is what most interests him, which is why, when you hear a classic line from an old song, like “the Boy in the Bubble and the baby with the baboon heart,” the words are so rhythmic that they very nearly are the rhythm. Here in the studio, the challenge for the band is re-creating all the sounds that Simon has layered into his new songs. There are guitars and drums, more recondite instruments like the glass harp and angklung, and ambient noises that Simon’s wife, the singer Edie Brickell, record­ed on a small digital tape machine during a family trip to Africa: humming insects, tent zippers, grunting wildebeests. “I put the wildebeest in just to change the sound,” Simon says. “Nobody’ll notice, but changing the textures makes you hear more clearly. Without these sounds, it’s like I’m just playing a guitar in a room, which I don’t like. So I put in ambience. I put in the African night.”

All this is no problem for the virtuosos in Simon’s band. But what is that faint thock, thock, thock everyone hears when the sound engineer plays back the track from the album? Even Simon isn’t sure. “It doesn’t have to be exactly like the record,” he tells the perplexed musicians. “It’s fine so long as we keep it sim­ple and a little weird.” But as the band practices “Rewrite,” Simon keeps stopping them, on average, every 20 seconds, to refine the number. His attention to detail is such that during rehearsals for his musical The Capeman, he kept the entire company waiting for half an hour while he explored the theater, testing the air for the ideal spot to place a gourd player. Comparing his approach to writing music with that of Paul McCartney, Simon says, “He doesn’t think of it in the same way as I do. He wants to capture his impulse. Me, I’m happy to spend a year and a half on a song. I’m willing to wrestle until I cry uncle or I beat it. I think that way — I got ya now! Gotcha!

Simon’s remnant hair is gray, but otherwise his essential fea­tures remain intact: Under the awning of the ever-present hat or baseball cap are those silent eyes, the alert, expressive brows, the chesty boxer’s frame, the oft-pursed lips that indicate a watchful presence. At five foot four, Simon has no illusions about his image as a rock star; he once went through a pe­riod when he so disliked his own appearance that he refused to look at photographs of himself. “It’s easier not to play the game of rock star when you don’t look like one,” says McCartney. “He looks professorial — you can imagine him teaching you literature. The fame game can make people be­lieve their own legends and go out of control. He has in-built protection.” In the studio, Simon is dry and deadpan. At one point during rehearsal, Jim Oblon, the youngest member of the band, puts down his drumsticks, moves to the microphone and starts riffing over the melody.

“If I do that, will I get more girls after the show?” Oblon asks.

“You’re in the wrong band,” Simon tells him. “Or at least a decade late.”

ONE DAY NOT LONG AGO, DONALD FAGEN, OF STEELY DAN, WHO HAS ADMIRED SIMON’S WORK FOR decades but knows him only slightly, offered up a spontaneous theory of Simon’s childhood. “There’s a certain kind of New York Jew,” Fagen began, “almost a stereotype, really, to whom music and baseball are very important. I think it has to do with the parents. The parents are either immigrants or first-generation Americans who felt like outsiders, and assimilation was the key thought — they gravitated to black music and baseball looking for an alternative culture. My parents forced me to get a crew cut; they wanted me to be an astronaut. I wouldn’t be surprised if all that’s true in Paul’s case.”

When I recount this to Simon, he says Fagen isn’t far from the truth. Simon’s parents were first-generation American Jews. His mother, Belle, taught at a Queens elementary school, and his father, Lou, was a professional musician who played the bass “to put food on the table.” They lived on 70th Road in Kew Gar­dens Hills, in the middle of a monochrome block of identical, low-slung, attached brick houses. But to Simon, his childhood comes back to him in nice bright colors, teeming with ballplay­ers, hoodlums — “I was a wanna-be gang member” — street-cor­ner doo-wop groups, satin summers and clear winter nights. “I got real infatuated with lights,” he says. “I was lying in bed and they were building new houses in the lots across the street. Snow fell at night. The workmen built a bonfire. The light from the bonfire magnified by snow, the way it moved across the ceiling — I loved it. An orange flickering thing.”

It was Art Garfunkel who long ago pointed out to Simon that, even in boyhood, Simon had an unusual interest in people who liked to do the things Simon liked to do but had different ways of doing them. In those days, Simon would put his baseball glove over the handles of his Schwinn bicycle with the baseball cards in the wheel spokes — “to sound like a motor” — and leave Kew Gardens Hills in search of pickup games in far-flung Italian and Irish neighborhoods. Unknown schoolyards were exotic places to Simon, and he enjoyed the company of strangers. “Artie used to say, ‘You were the kid who knew more kids in different neigh­borhoods,'” says Simon. “I was a ballplayer. I’d go on my bike, and I’d hustle kids in stickball.” Simon has essentially approached his entire creative life as a series of bike trips, riding in and out of different musical neighborhoods, responding to something new.

As a boy, Simon often crooned to himself in the bathroom with the lights off, enjoying the reverb of the tiles — hence, “Hello dark­ness, my old friend.” But he was singing alone in his bedroom with the baseball pennants on the wall when the door opened, and there was Lou Simon telling him what a nice voice he had. Nobody had ever said that to him before. “He was in a tuxedo, going out the door to a club date,” Simon recalls. “My father was a Yankee fan. I used to listen to games with my father. He was a nice guy. Fun. Funny. Smart. He didn’t play with me as much as I played with my kids. He was at work until late at night.” Some­times, at two in the morning, when Lou Simon at last turned on to 70th Road, he couldn’t tell which driveway was his and pulled his car into the wrong one. “It really frustrated him,” says Simon. “We had to be quiet in the morning. I used to watch him shave. He used to say, ‘I really don’t feel like working to­night,’ a feeling I came to understand.

It was baseball that introduced Simon to rock & roll. He was the sort of Yankee fan who kept a scorebook and tore up Red Sox cards as a matter of principle. One day, as he was listening to his radio, waiting for the broadcast of the game to begin, the DJ said, “I have a new record. It’s the worst thing I’ve ever heard. If this is a hit, I’ll eat my hat.” The song was “Gee,” a doo-wop number by the Crows. Simon was transfixed. “This is the first thing this guy’s played that I like!” he thought.

Simon was the kind of categorical listener who knew precise­ly what he liked, and how much he liked it. His first favorite song was a doo-wop hit, “Sincerely” by Harvey and the Moonglows. His two “unattainable pinnacles” remain Elvis Presley’s song “Mystery Train” and the Bo Diddley beat. The beacon in the dis­tance he might reach someday is the great Iowa harmony singers Don and Phil Everly. “I wasn’t exposed to poetry at all as a boy,” Simon says. “But the music I heard conjured up a kind of poetry. Seemed very mysterious to me. A kind of delightful mysterious. I thought the name Elvis Presley was one of the weirdest names I ever heard.” As he sorted through it all, trying to find his own voice, he realized he could never sound raunchy and Southern like Presley, so he went the other way, following softer examples like Sam Cooke, Clyde McPhatter, and the Fleetwoods.

All the sounds Simon liked as a boy remain fresh in him today, and he continues to draw from them. The new album’s title song, “So Beautiful or So What,” features what he says is “one of my favorite Bo Diddley rhythms.” (It also references the Miles Davis tune “So What.”) In his earlier songs, Simon is prone to naming his favorite doo-wop groups and their hits. His work references such a broad geography of music that he is sometimes accused of being someone, as he puts it, who “flits around from culture to culture,” but to him, when he encounters something new that he likes, an inevitable part of the appeal is that it doesn’t really seem new at all. In 1985, when Simon traveled to South Africa and began to work with Ladysmith Black Mambazo, their harmonies so closely resembled the doo-wop of his childhood that he found their sound to be “a very familiar thing.”

SIMON AND GARFUNKEL MET DURING A GRADE SCHOOL PRODUCTION OF “ALICE IN WONDERLAND.” Simon played the White Rabbit and Garfunkel the Cheshire Cat. (A musicologist will someday be tempted to make something of this; he shouldn’t.) Soon the two boys were hanging out in their basements, imitating the Everly Brothers. At a time when most people didn’t think of singing pop songs as a serious musical en­deavor, Garfunkel shared Simon’s belief that in rock & roll there were vast creative possibilities for two teenagers who liked to mesh their voices. Even at that point, both boys had a profes­sional sense of commitment to music: They would do whatever it took. “I missed baseball practice once for a talent show,” says Simon. “The baseball coach, he didn’t like it. He told me, ‘Paul, you better make up your mind if you want to play baseball or you want to sing. You gotta get serious, Paul.'”

At 16, using the stage name Tom and Jerry, the two had the first of their many hits, a teenage come-hither called “Hey, Schoolgirl.” As Simon and Garfunkel, it took them longer. While Garfunkel pursued mathematics at Columbia, Simon studied English at Queens College and worked jobs in the music indus­try. One of his employers was Am)’ Records, a small company on Broadway near the Brill Building. “After school, I’d come into town and listen to masters people sent in,” Simon says. “I knew where that record company was — the bottom. They got nothing choice. I didn’t accept anything.” Another year, Simon was hired by the song publisher E.B. Marks and charged with peddling weary chestnuts from the Marks catalog like “The Peanut Ven­dor” to record companies. “I couldn’t sell one song,” says Simon. “It was rock & roll’s time. I felt bad, I couldn’t get anything sold, and so I’d write a song and let them publish it.”

Each time he met with a record company, Simon had to write up a report. One day, the man who owned E.B. Marks called him in and asked, “Who wrote this report?” Simon answered that he had. The man said, “No, you didn’t.” Simon said, “Yes, I did.”The man insisted, “No, you didn’t. It’s written too well.” Simon lost his temper. “I majored in English lit,” he told the man. “And fuck you, I quit.” From then on, he decided, he would publish every one of his songs himself. He took the next one to Columbia Rec­ords and met with the producer Tom Wilson. “I’d like to use that song with this group the Pilgrims,” Wilson told him. Simon said, “I sing it with a friend. Can we sing it for you?” Wilson agreed. “So,” says Simon, “Artie and I go up there and sing ‘The Sound of Silence.’ We sang it, and to our surprise, they signed us.”

That was in 1964. Columbia put out the album Wednesday Morning, 3 A.M. At first, it went nowhere. “By that time,” Simon says, “the Beatles already existed, the Stones already existed, Dylan already existed. There seemed to be no place to fit in. You couldn’t get up to the feeding trough. They had covered the land­scape. But they didn’t have what we had: New York doo-wop.”

Wilson went back into the studio, and without telling Simon or Garfunkel, he added rock instrumentation to “The Sound of Silence” and re-released it. So it was that one Saturday night in 1966, the two best friends were sitting in Simon’s car, parked on a quiet corner in Kew Gardens Hills. They had no gigs, no dates, nowhere to go and nothing to do. The car radio was switched on, and as they talked, the DJ was concluding the weekly countdown of the nation’s top hits. At last, he reached Number One. “Hello darkness, my old friend,” it began.

Garfunkel spoke first. “Now those guys,” he said, “must be having a big life!”

Simon still loves the memory. “Artie!” he says. “He was funny. I guess people like the idea that we can’t stand each other. That we don’t get along. We were best friends. Nobody made me laugh like Artie.”

Simon and Garfunkel was, Simon says, “an incredible adventure. Just to travel, get on a plane, go to a town I’d never been to. At the beginning, we were thrilled to stay in a Holiday Inn: ‘Oh, great! They have a vibrating bed!’ The kids would invite us to their parties. We were only a couple of years older than they were. Artie sometimes hitchhiked from one gig to another.”

With their five albums in six years, Simon and Garfunkel created among the most melodic, beautifully interwoven harmonies in American musical history. In the process they became something like musical brothers. “We really have a unique blend of voices,” says Simon. “It pulls you back, that blend.” But as rewarding as the collaboration was, it also pushed them apart. Both were willful and sharp-witted, bright and sensitive. “I’ve had terrible fights with Artie about things,” Simon says. “Some­times artistic things. But Artie doesn’t write. We didn’t really fight until ‘Bridge Over Troubled Water.’ That had a lot to do with Artie making a movie at the same time.”

The movie was Catch-22, directed by Mike Nichols, who had commissioned “Mrs. Robinson” for The Graduate. Since Simon wrote all the songs, it was understandable that Garfunkel might want a little artistic independence — might wish to create a role for himself rather than simply interpreting his shared part. But while Garfunkel was down in Sonora, Mexico, waiting and wait­ing for Nichols to film his scenes, Simon was working unassist­ed on their next album and feeling abandoned. He set down one of his last songs for Simon and Garfunkel, “The Only Living Boy in New York,” in which “Tom” flies down to Mexico, leav­ing the singer with “nothing to do today but smile.” Something else Simon was working on while Garfunkel was in Mexico was a soaring hymn he still feels Garfunkel’s voice alone is “particu­larly suited to.” After the record came out, Garfunkel would go onstage and perform “Bridge Over Troubled Water,” and as he did, Simon would stand in the wings, anticipating the torrents of applause to follow and thinking, “That’s my song, man.”

Soon the friends went their separate ways. “Simon and Garfun­kel is a minefield,” Simon says now. “It’s very hard to be in a duo. I was very liberated by the breakup of Simon and Garfunkel.”

FOUR DECADES LATER, “BRIDGE OVER TROUBLED WATER” HAS BEEN PLAYED ON THE RADIO MORE THAN 7 million times. In all, songs written by Simon have been broad­cast over 100 million times. Three of his 16 albums — Bridge Over Troubled Water, Still Crazy After All These Years and Graceland — have won the Grammy for Best Album. Simon has received a sufficient number of lifetime-achievement awards, from the likes of the Kennedy Center and the Library of Congress, that there is no one who would suggest he acted imprudently when he left Brooklyn Law School after a “wasted year” in 1963, and set off hitchhiking, looking for America with only a guitar and a suitcase.

Still, there is a stigma about Simon that might be summarized as the belief in some critical corners that he hasn’t suffered enough. The complaint seems to be that Simon is too literate, too earnest, too neurotic — in short, too much like a music critic. “He has always been the smart, bourgeois, fussy wimp who makes some self-styled rockers want to kick sand in his face,” is how Jon Pareles once described him in The New York Times. When Simon, searching for inspiration, traveled to apartheid-era South Africa in 1985 to record with local black musicians, American critics called him a cultural opportun­ist. And when he spent the early 1990s working on his Broadway musical, The Capeman, they portrayed him as an interloping egomaniac.

Simon experiences the world in such a full and detailed way, it’s easy to imagine the vivid impressions he must have accumulat­ed across more than 50 years at the center of American popular music. But though he applauds Stephen Sondheim for exacting “delicious” revenge in his recent memoir, Finishing the Hat, don’t expect any such revelations from Simon. These days he seems like a novelist in late autumn, working as hard as ever, but taking con­tented pleasure in family, friends and the daily newspaper. He has forsaken his penthouse duplex overlooking Central Park for the suburbs, where life as the only living boy in New Canaan seems to suit him. He now writes most of his songs in the car, a black SUV he selected for its acoustics. He sings to himself as he ferries his three kids around, and then, when he hits on something good, he remembers it until he gets home. “I don’t talk that much about my life, my past,” he tells me, sitting in his office in midtown Manhattan. Hearing him say those last two words in his familiar, gently longing outer-borough baritone brings to mind the weary man in Simon’s song “Gone at Last,” who takes harbor at a truck stop on a snowy night for some “thinking about my past.”

If you’ve spent your life listening to Simon sing about scarred, resilient people grappling with life’s disappointments, there’s something affirming about how unchanged his voice sounds as he approaches his 70th birthday. You have only to listen to the precise way he enunciates his suffixes, the many pauses he favors in conversa­tion, to grasp that clarity and emotional precision are crucial to him. His voice is often faulted for its limitations of size, but it has the advantage of New York character. In the same way the city’s Upper West Side can feel like a Woody Allen movie in real time, it’s easy to hear every word spoken by New Yorkers as lyrics from a Paul Simon song: your barber when he tells you, “That seems to be OK,” or the woman in line getting coffee, rearranging her position on “this guy I had a little bit of a thing with.”

But Simon believes that his voice is part of what makes people hard on him. “One of my deficiencies is my voice sounds sincere,” he says. “I’ve tried to sound ironic. I don’t. I can’t. Dylan, every­thing he sings has two meanings. He’s telling you the truth and making fun of you at the same time. I sound sincere every time. Rock & roll has a lot to do with image. If that’s not your strength, people find fault with the work.”

In particular, Simon has spent his professional life being con­demned for not being Dylan. “There’s always some kind of com­parison between us,” he says. “I usually come in second. I don’t like coming in second. In the very, very beginning, when we were first signed to Columbia, I really admired Dylan’s work. The Sound of Silence’ wouldn’t have been written if it weren’t for Dylan. But I left that feeling around The Graduate and ‘Mrs. Robinson.’ They weren’t folky anymore.”

Simon’s office is in the Brill Building on Broadway. In the late 1950s and early 1960s, when Simon was coming into Manhat­tan by subway from Queens to hustle songs, the Brill Building was for popular songwriters what Silicon Valley is for computer programmers today. There are art deco ceiling lamps, Italian chairs, plants, an Asian screen, a desk that doesn’t look as though it has seen much service and a piano that seems more experienced. The books that Simon has on hand include biographies of Bruce Springsteen and Sylvia Plath stacked with a collection of John Berryman’s poetry. Simon agrees with his friend, the poet Billy Collins, that song lyrics are not poems. “I don’t like the honor­ific lifting up of something else to poetry,” Collins says. “Poet­ry in motion and so on. I hold rock lyrics to their own standard. ‘Whiter Shade of Pale,’you have no idea what that means, it’s just a great song.” But Paul McCartney disagrees. “He’s a poet!” Mc­Cartney says of Simon. “The same rules of poetry apply to a song­writer. Economy, phrase, rhythm. Allen Ginsberg always wanted you to say, ‘Is this a song or a poem?’ If it was a song, he’d leave you alone. If it was a poem, he’d knock it to pieces.”

For all of his celebrity, when Simon goes shopping for groceries, he is still capable of convincing himself that nobody notices him as he walks the aisles. Then, after he makes his purchas­es, he feels flustered to find people approaching him. “Paul Mc­Cartney is always aware that somebody’s watching him,” Simon says. “I never think anybody’s watching me. I’m naive.” Like many diffident writers who bring intimate themes from their own life into their work, there seems to be a necessary disconnect in Simon that wants always to consider the flashes of self-portrait that are layered into his songs as lyrics rather than life. “I don’t usually write autobiographically anymore,” he says. But people approach Simon in supermarket checkout lines part­ly because he has written so well about that most enduringly seductive subject, doomed romances. Among Simon and Garfunkel’s more popular songs are “Kathy’s Song” and “America,” which feature Simon’s former girlfriend, Kathy Chitty. “Before I knew him, I knew Kathy,” says Simon’s friend, Saturday Night Live producer Lorne Michaels, voicing an impression shared by many fans. Simon wrote the last verse of “Bridge Over Troubled Water” — which begins “Sail on, silvergirl” — after his first wife, Peggy Harper, noticed her first gray hairs. The medley of love-damaged songs he wrote with his second wife, the actress Carrie Fisher, in mind, includes “Hearts and Bones,” “Allergies” and “She Moves On,” in which Simon describes a man “abandoned, forsaken in her cold coffee eyes.”

All this, of course, can be hard on the mortals who inspired the timeless songs. When discussing the interplay of personal history and imagination, Simon’s desire “not to hurt anybody” always trumps disclosure. When I ask Simon about his song “I Do It for Your Love,” he says, “That’s about my first wife, Peggy. I met Peggy … better not to go into that!” Harper is a reserved woman from a hamlet in the east Tennessee hills. Carrie Fisher, on the other hand, is a former Hollywood princess who has seemed to spend her life getting into everything. She has written that Simon is a “magic person” and described herself as a “bitch,” explaining that Simon “had to put up with a lot” during their dozen years together. Simon’s response? “I don’t want to talk about Carrie,” he says. “I don’t mean I dislike her. I don’t dislike Carrie Fisher. I just don’t want to get into it. She’s a writer. She’s entitled to her life and to write about it as she wishes.”

It hasn’t escaped Simon’s notice that the more he kept his personal life to himself, the better life got. “At a certain point,” he says, “you begin to realize about your life and your private affairs that it’s inappropriate that it should be entertainment for some­body else. There’s no requirement that I tell how I hurt and how I feel. It’s a mistake you make early on. I see Eminem out there talking about his family, his kids, and I think 10 or 15 years from now he’ll regret it.” Simon refuses to discuss his children, including his eldest son, Harper, who has struggled to define himself as a musician since he toured with his dad on Graceland at age 14. “It’s a very high bar that he set,” Harper has said. “If you can’t be up at that level, why bother, you know?”

Near the entrance to Simon’s office, there are several framed pictures of baseball players, among them Jackie Robinson, the Negro Leagues star Buck O’Neil, Mickey Mantle, Joe DiMaggio and a fleet of other New York Yankees. “I like baseball,” he says. “Probably my favorite thing. When it comes to the end of life, I’ll say it was baseball and music. That’ll be it.” What Simon sa­vors most about the sport is line drives. “That feeling of the ball hitting the bat so perfectly, you don’t feel it,” he says. “It’s like writing a great line. You don’t even feel it. You think, Ahhh! It’s perfectly concise. Anybody who has not experienced it can’t un­derstand.” His favorite player was Mantle, who, when he met Simon, wanted to know why, if that was the case, DiMaggio was the one Simon had immortalized in song. Simon explained about syllables, how it helps when they glide along for a while. When Simon encountered DiMaggio in an Italian restaurant, the Yan­kee Clipper also had questions: “What does that mean — Where have you gone?” He let Simon know he hadn’t gone anywhere. He was doing ads for Mr. Coffee. Simon told DiMaggio about the potency of vanishing heroes. As for the line itself, how it came to him at age 26, all Simon has ever been able to say is, “I don’t know where it came from, but all of a sudden it was there.”

Leaning against a wall in the near corner of the office, not far from the baseball display, is a double bass. The instrument is so large that once you notice it, the bass seems to loom over the room. Simon says it belonged to his father, who remains a strong presence for him. The New York Times once reported that the two had a “famously tortured relationship.” This was said especially to be true after Simon became celebrated for making a kind of music that Lou Simon considered trivial. Not true, Simon says with indignation. “I imagine he was amazed and kind of happy for me,” he says. “I had a very good relationship with my moth­er and father. Complicated with my father, but certainly loving. I think it was fame. For my mother it was pure joy. For my father — he never said this — there came a point where enough was enough. The only thing I can remember — and my father is the person who most influenced my thinking and my life — he said, ‘Of course I’m very happy for you. I can’t argue with your suc­cess. But is that really what you want to be, a rock star?’ I said, ‘Yeah! Why not? What should I be? What am I supposed to be?’ He said, ‘A teacher.'”

In the late Seventies, Lou Simon abruptly put down his bass, went back to school at New York University, received a doctorate in linguistics, and became a professor of education at City College. “It’s complicated,” says Simon. “Here’s a guy, a musician all his life. In his fifties, he leaves and goes and gets his Ph.D. Extraordinary. He’s a star in his own right, but he’s also the father of Paul Simon. For him, it was a mix.” Simon pauses. “It’s very hard to know what your father is thinking,” he says. “I was working on St. Lucia when he died. His health had been failing. He took a nap and he died.”

SCATTERED THROUGHOUT SIMON’S OFFICE ARE PHOTOS OF ARTIE, DION, AL GORE, LORNE MICHAELS, PHILIP Glass, Leonard Bernstein, the Brazilian singer Milton Nascimento, the Smothers Brothers, Kate Smith, the wife and kids. A handsome walnut cabinet houses a Kodachrome-era hi-fi. “This stuff is old,” Simon says about the stereo. “I’m not a tech-nophile.” Along the walls there is a weekend watercolor portrait of Simon painted by his mother, the framed string arrangement Simon commissioned for “Bridge Over Trou­bled Water” that the composer hasti­ly mistitled “Like a Pitcher of Water” and a letter from George Gershwin, in which he pitches himself to one A.M. Wattenberg: “Our Astaire picture, Shall We Dance, looks first-rate.”

Simon smiles. “Songwriter insecuri­ty,” he says. “I never met a secure writ­er. They’re all competitive, and they’re all paying attention to what people say about them, which is what makes peo­ple crazy.” Is this true of him? “I don’t think of myself as insecure in the world, he replies quietly. I say that he seems like a self-confident person who prefers the periph­ery. “Periphery is true,” he says. I mention the “immobilizing” depression he once described after the failures of his film and album One-Trick Pony, and the simultaneous disintegration of his relationship with Carrie Fisher. “There’ve been times I’ve been depressed,” he says even more quietly. “Not to say there haven’t been times of self-doubt. I wouldn’t say I was happy-go-lucky.”

You don’t have to recall the cover photograph of Simon’s brilliant self-titled 1972 debut solo album, in which his face is half-obscured by a thick frame of parka fur, to sense that he is the kind of man who can be a little hard on himself. But if Simon has seemed furtive across his long career, it’s because he isn’t really nonchalant about anything. The singer-songwriter Randy New- man recalls playing catcher in a wiffle-ball game on Long Island when Simon came to bat. “I could hear him talking to himself,” recalls Newman, who has known Simon casually for years. “Real­ly competitive. Unusually competitive. He wants to win at stuff.” As Simon himself often stresses, his music is the best of him — “as opposed to when I’m being a real asshole and then later regretting it. Everybody famous is an asshole at times, and the only thing interesting about it is the excuse for why you’re such an asshole.”

Anyone who knows Simon’s best songs realizes how musically invested he is in that question of why flawed men and women are the way they are. Vulnerability is his great subject. Like all the great artists, he’s more interested in process than resolution, in the smallest subtleties of feeling. His characters are downcast, unguarded people trying to keep up their hopes (“I do believe, if I hadn’t met you, I might still be sinking fast”) and striving to con­nect (“You don’t feel you could love me, but I feel you could”). To those who know him, like Billy Collins, Simon is “a good example of the examined life” — something I come to appreciate at the stu­dio early one evening, when Simon tells me how a long, disorient­ing interval in his life became a single perfect line in a song.

It was a decade ago, and Simon was suddenly overcome with self-loathing. “I really attacked myself,” he recalls. “It was a bru­tal attack. I didn’t tell anybody. It was like a voice inside me was really attacking me.” When he tried to defend himself against the assault from within, the voice wouldn’t let him. “You got it wrong,” it told him. “This isn’t a trial. It’s a sentencing. We’re not interested in how good you talk. That’s just a cover-up.”

At the time, Simon was having trouble with pain in both hands and he worried about his future ability to play an instrument. He visited a doctor, and after the physical examination, Simon told him about the voice that made him feel that everything he did was wrong. The doctor asked Simon if he was game for some­thing unconventional. Sure, said Simon. The doctor knew a for­mer psychiatrist, a man of great skill, who had closed his practice and gone to work for a church in Baltimore. Simon telephoned the man. “I told him the whole thing about my attack on my ego,” he says. In response, the man in Baltimore said that encounter­ing an extraordinarily harsh inner voice is not an uncommon ex­perience for writers. The man asked Simon to choose a voice he thought of as comic — perhaps Bugs Bunny’s voice — and told him to try to hear the harsh voice as Bugs. Then, the man said, Simon should take the now-defused voice and put it under his shoe.

“I understood his point,” Simon says. “You’re fooled because it’s your inner voice. It’s not uncommon for people to get down on themselves and hit all their own wounded spots. You can really hurt yourself. This was a way of saying don’t pay attention to yourself. It was good advice.” The idea eventually showed up on the album Surprise, in “Sure Don’t Feel Like Love,” when Simon sings, “Who’s that conscience sticking on the sole of my shoe?”

During another conversation at the rehearsal studio, Simon tells me about a book, A Giacometti Portrait, he’d read years ago that was still strikingly vivid for him. The book is writer James Lord’s account of being painted by his friend, the Swiss artist Alberto Giacometti. “Every day, Giacometti finished the portrait and said it was awful,” Simon recounts enthusiastically. “The degree to which he beats himself up is hilarious. I can be pret­ty rough on myself. But him — he really beat himself up. He’d get better and better and then say, ‘This is just unacceptable! One thing the world will be spared is this crap, this kind of mediocri­ty out of me, talentless nothing that I am.’ He’d do this over and over until Lord told him, ‘Don’t touch it, you’ve got it now.’ But Giacometti took it apart and redid it and did it better. That constant editing and self-criticism — I liked it.”

Other artists are often surprised by the lengths to which Simon will go to “destroy everything with great bravery,” as Giacometti put it. A few years ago, Simon agreed to sing one of his forlorn masterpieces, “I Do It for Your Love,” on an album of covers the jazz pianist Herbie Hancock was making. But as the two musicians consulted about the song, Simon surprised Hancock by suggesting that they significantly rework the tune, reducing its complex structure to a single chord and switching it to a minor key. “The recording we did is a completely different idea of the song from the one he wrote,” Hancock marvels. Simon’s musical “curiosity” reminded Hancock of his old boss, Miles Davis. “Miles and Paul aren’t in boxes,” he says. “A couple of geniuses with heads full of ideas.”

WITH SIMON, IT ALWAYS SEEMS TO COME BACK AROUND TO WHERE IT ALL COMES FROM, how everything put together gets put together. During a recent public conversation with Billy Collins at a college in Florida, Simon told the audience about “Love and Hard Times,” one of the new songs on So Beautiful or So What, and he spoke in such detail about his process that he brought to mind for Collins “a Ferrari mechanic taking the engine apart. He had a very clear sense how his music is con­structed. The old question: Does the music or the lyric come first? For him, clearly the beat comes first. He’s not just Rhymin’ Simon, he’s Rhythmic Simon. He picked up his guitar and played ‘Mystery Train’ and said, ‘Forty percent of my music is based on that.’ More than most writers, he’s willing to admit his music is an assemblage of different influences.”

By reimagining existing forms of music and making surprising linkag­es across a vast palette of sound pat- terns old and new, Simon has always been ahead of his time. In 1965, at Theatre de l’Est Parisien, he heard the Peruvian band Los Incas using charangos and pan flutes to play the Andean folk song “El Condor Pasa,” which he subsequently adapted into the Simon and Garfunkel song “If I Could.” “I’d never heard those in­struments,” he says. “I loved it. Maybe I have the capacity to have my emotions touched by sounds and rhythms of different cul­tures as well as the first stuff I heard on the radio in adolescence, when most people’s emotions are touched.”

In 1971, for his first solo album, Simon returned to Paris and recorded a broken-shoed shimmy called “Hobo’s Blues” with the legendary jazz violinist Stéphane Grappelli. That same year, he visited Jamaica. He had heard Jimmy Cliffs ska song “Vietnam,” and it inspired a song about a smaller family trag­edy from Simon. “If you really want something,” he says, “you gotta go to where they play it.” When he got to Kingston, he met up with members of Cliffs band, Toots and the Maytals. “I showed them my song and said, ‘I want to do a ska version.’ They said, ‘We don’t do ska anymore.’ I said, ‘What do you do?’ They said, ‘We play reggae.’ I said, ‘What’s that sound like?’ They played it. I said, ‘Let’s do it!'” The title of Simon’s song was itself a sly allusion to provenance. On a menu at a restau­rant in Chinatown, he saw a chicken and egg dish called “Moth­er and Child Reunion.” The song, as Simon puts it, “became the first reggae hit by a non-Jamaican white guy outside Jamaica.”

By that time, Simon’s ambitions were growing beyond the diverse songs he was writing for his first three solo albums. I n 1977, Woody Allen cast him in Annie Hall, as the music producer for whom Annie leaves Alvy Singer. “Allen’s instructions were really simple,” recalls Simon. “Come in, say anything you want, and invite her to a party. Be sure you say it’s gonna be ‘very mellow.’ When he first wrote the part, it was all wrong. I said, ‘He’s not gonna be a stupid guy!’ Woody’s not a fan of rock & roll, as every­body knows. But he let me pick everything — the coke spoon dangling around my neck, the stuff I said about Jack and Anjelica coming to my party.”