As a minstrel, Paul Simon looked like a nebbish, wrote like a poet, and sang like a dream. Now in his mid-70s, he’s in the midst of a tour of 29 cities in the U.S., Canada, Scandinavia, Belgium, and the British Isles—his farewell to performing after more than five decades. He’s sold uncountable millions of records, contributed more than a dozen entries to the second Great American Song Book, been admitted to every imaginable musical hall of fame, and gotten so rich that he once reimbursed his record company more than a million dollars for a flop album. And yet, he can still be mopey after all these years.

Anyone who grew up Jewish in New York, especially in Manhattan and Queens in the 1940s and ’50s, would recognize Simon as a type: small, smart, with middle-class parents keen on assimilation, a schoolyard ball player, baseball-card collector, Yankee fan, drawn to folk music and doo-wop, just religious enough to have a bar mitzvah. Ralph Lauren’s father, Frank Lifshitz, was a housepainter in the Bronx. Paul Simon’s father, who had an exceptionally high IQ, played the string bass, led his own dance band at Roseland, and plucked in the house bands at CBS and NBC. His mother was an elementary-school teacher. When Simon wrote the line, “Where have you gone, Joe DiMaggio?” he knew what he was talking about.

For all his accomplishments, Simon is not all that compelling beyond his music. That’s a problem for the readers of Paul Simon: The Life, the and-then-he wrote-and-then-he-broke-up-with–Art Garfunkel–again new book by Robert Hilburn, a longtime pop-music critic for the Los Angeles Times. It’s an all-but-authorized biography based on hundreds of hours of interviews with Simon and access to many people close to him. If you want to know why Simon put the opaque line, “The cross is in the ballpark” in the song “The Obvious Child” on The Rhythm of the Saints, the album he made with the black drummers of Salvador in northeast Brazil, this is the book for you. If you want to feel you know Simon the way, for instance, readers of James Kaplan’s two-volume biography of Frank Sinatra feel they know Sinatra, you’ll have to wait.

Still, Simon’s progression from Kew Gardens Hills in deepest parochial Queens to the Valhalla of the Rock and Roll Hall of Fame is a story worth telling. His first musical epiphany, Hilburn writes, came the summer he was 12. He wasn’t much interested in the piano lessons his father pressed on him or the novelty records and ballads like Jo Stafford’s “You Belong to Me” that dominated the pop-music stations. One day, he turned on the radio to hear Mel Allen calling a Yankee game and instead found a disk jockey playing “Gee,” an infectious doo-wop number by the Crows. Soon, he’d caught the Moonglows’ lilting “Sincerely,” and the Penguins’ “Earth Angel,” the love-sick teen anthem that’s still as evocative to those who heard it first as the madeleine was to Proust. He began singing the songs into a wire recorder with a kid with a sweet voice he’d first met in the fourth grade named Art Garfunkel. Later that year, he and Garfunkel teamed up to sing “Sh Boom,” the big hit by the Crew Cuts, at a school assembly.

Simon had taken up the guitar and was star-struck by Elvis Presley. But at barely five-and-a-half feet, he knew that the rangy, stunning Elvis could never be his model. Instead, he settled on the rockabilly Everly Brothers, whose “Bye, Bye Love” was a sensation and whose ferocious feuding became a template for Simon and Garfunkel’s next 50 years of passive and active aggression. He wrote a song called “Hey, Schoolgirl” with Garfunkel, made a $10 acetate copy at a recording studio, and began trying to peddle it. He was 16. A tiny record label named Big signed them up. Simon and Garfunkel were launched—except that their producer renamed them Tom and Jerry. Their first single sold some, but two later ones flopped, and Garfunkel went off to study architecture at Columbia. Simon spent hours back in Kew Gardens Hills, strumming his guitar in the dark in the bathroom where his music resonated off the tiles.

It’s just a stroke of genius from there to “Hello darkness, my old friend”—that was, of course, the first line of “The Sounds of Silence,” the 1963 song and album that transformed Tom and Jerry into Simon and Garfunkel. In between, Simon went to Queens College and patrolled the Brill building, hawking his own songs and earning pocket money singing other people’s on demo recordings. He also haunted the folk-music clubs in Greenwich Village, where he felt treated like an outsider because he hailed from bourgeois Queens rather than the Ozarks or the Dust Bowl. He fumed for years because he caught Bob Dylan giggling while Simon strummed one of his folky numbers. He played the folk clubs in Great Britain, too. At 22, he was a young old pro, savvy in the recording studio and on stage.

“The Sound of Silence,” later used as a motif in The Graduate, sold 3 million albums, and the hits just kept on coming:  “I Am a Rock,” “Scarborough Fair,” “Homeward Bound,” “Mrs. Robinson,” “America,” “At the Zoo,” “Bridge over Troubled Waters,” “The Boxer.”  In 1966, he made the equivalent of $2.35 million in today’s money. Four years later, the “Bridge” album sold 8 million copies. Two years after that, Simon and Garfunkel’s Greatest Hits sold 14 million albums.

Watching those old performances on YouTube today, it’s easy to see their appeal. Garfunkel has that adolescent, slightly androgynous look that enraptures young women and poses no threat to their boyfriends. His angelic voice mates with Simon’s to produce a wistful innocence evocative of brave hope, lost love, and teen alienation. Off-stage, Garfunkel was churning with resentment. He’d never forgotten that Simon and their producer had gone behind his back in the Tom and Jerry days to record a solo single for Paul. Simon was obsessed with being short, and Garfunkel would taunt him: “I’ll always be taller than you.” The big break came over Garfunkel’s budding movie career. Mike Nichols had cast both men in his 1970 film of Joseph Heller’s Catch-22. Garfunkel got fourth billing, Simon’s scenes were cut. The next year, Nichols gave Garfunkel a major part in Carnal Knowledge. The filming in Mexico took forever while Simon seethed back in New York waiting to work on their next album. Over the next 40 years, they kept making up for special concerts and reunion tours, a late one with the Everly Brothers, who got along even worse than they did.

His standoff with Garfunkel mirrored Simon’s lifelong pattern with women. His first real girlfriend was an unsophisticated British girl he met on tour and later dropped. He married his manager’s ex-wife, divorced her, took up with the actress Shelley Duvall, then dumped her for Carrie Fisher. He and Fisher drove each other crazy for ten years, several as husband and wife. “Who told you to fall in love with an actress?” chided his father-in-law, Eddie Fisher. His third marriage, to the singer and songwriter Edie Brickell, who is more than two decades younger, has lasted for more than 25 years.

Post-Garfunkel, Simon literally reengineered himself as a solo performer. The detailed descriptions of how Simon made his new music are the most engaging parts of the book. He’d never mastered musical notation, so Simon “composed” by noodling on his guitar until he found an intriguing riff, polishing the fragment and then adding it to others until he had a melody. Only then would he try to add a lyric, struggling for weeks over a single line that came to mind while driving or retrieving phrases from scribbled notebooks. Over time, the straightforward language of his S & G songs gave way to Dylanish interjections: “The mama pajama rolled out of bed,” “There’s a girl in New York City / Who calls herself the human trampoline,” “Song dogs barking at the break of dawn.”

To give his sound more authenticity, he augmented the polished studio musicians he’d always used with more exotic players. For one album, he went to Jamaica to work with the ska and reggae band from Jimmy Cliff’s albums. For another, he ventured down to Muscle Shoals in Alabama. He walked into the studio expecting to find black blues musicians and instead found a crew of down-home white guys. These forays paved the way for Simon’s big breakthrough—his 1986 Graceland album recorded in South Africa with the strutting, exuberant Ladysmith Black Mombaza group and later performed in concert with the great Xhosa star Miriam Makeba and trumpeter Hugh Masakela.

Graceland stirred a furor because Simon broke the anti-apartheid boycott against performing in South Africa, but it was a commercial and artistic triumph, with such numbers as “Diamonds on the Soles of Her Shoes,” “The Boy in the Bubble,” and the title song, a meditation on a visit to the Presley shrine. Simon had now become a leading popularizer of world music, a genre that was slow to win American fans. Four years later, he enlisted the throbbing Brazilian drummers for The Rhythm of the Saints, another exotic smash. It’s poignant to watch Simon in his bland T-shirt discreetly fingering his guitar in the midst of the churning Ladyship crew in their colorful dashikis or the frenetic drummers on the pastel Pelourinho Square in Bahia. None of them looks like Garfunkel, and Simon looks about as happy as he can manage.

Throughout his career, Simon battled his own recurrent sadness. He self-medicated by taking the show on the road or into the studio, where he could spend days with musicians perfecting tiny chunks of fresh sound that he would accumulate like Lego blocks and ultimately assemble into a song. No popular musician of our time worked as hard or evolved as much. And yet he’s never managed to transcend the emotional resonance of those half-century-old Simon and Garfunkel reveries.

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