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Paul Simon at 85: The Eternal Troubadour Who Redefined American Song
Born on October 13, 1941, in Newark, New Jersey, Paul Frederic Simon has spent more than six decades shaping the course of American popular music. From the folk-rock harmonies of Simon & Garfunkel to the revolutionary world music fusion of Graceland, Simon has consistently pushed the boundaries of what a songwriter can achieve, earning 16 Grammy Awards, a place in the Rock and Roll Hall of Fame (twice), and recognition as one of Time magazine's "100 People Who Shaped the World". As he celebrates his 85th birthday, his legacy stands as one of the most remarkable in the history of recorded music.
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Roots and Early Life
Paul Simon was born into a Hungarian-Jewish family in Newark, New Jersey. His mother, Belle, was an elementary school teacher, and his father, Louis, was a college professor and professional musician who played bass on the radio. The family later moved to Queens, New York, where Simon attended Forest Hills High School alongside Art Garfunkel, a classmate he had met at age 11. The young Simon was a high school baseball star, but music would soon become his true calling.
The musical influences that shaped Simon's early development were deeply rooted in the urban soundscape of 1950s New York. "The music was city doo-wop out of gospel quartets, with a little Puerto Rican mix in the rhythm," he later recalled. Among his earliest heroes were the Moonglows, the Penguins, and Frankie Lymon. The Everly Brothers, however, held a special place in his musical education. "Artie and I, we really learned to sing harmony by learning the Everly Brothers," Simon said. "Their sound was something that we strived for, that kind of buzz that you get, you know, when the blend is just right. You couldn't tell who was singing lead because both parts were so beautiful and sung so beautifully".

In 1957, while still in high school, Simon and Garfunkel formed a duo called Tom and Jerry, writing and recording the single "Hey Schoolgirl". The song sold more than 100,000 copies and earned the teenagers an appearance on American Bandstand and their first placement on the Billboard charts. The duo separated after high school, with Simon briefly attending Brooklyn Law School before completing a B.A. in English at Queens College in 1963.
The Simon & Garfunkel Era
The reunion of Simon and Garfunkel in 1964 marked the beginning of one of the most influential partnerships in popular music history. Signing with Columbia Records, they released their debut album Wednesday Morning, 3 A.M. that same year. The album initially sold poorly, and Simon traveled to England to pursue the burgeoning folk scene there, performing in small clubs and honing his craft as a solo artist. He later immortalized this period in "Homeward Bound": "one night stands / my suitcase and guitar in hand / every stop...neatly planned / for a poet and a one-man band".

Everything changed when producer Tom Wilson overdubbed electric instruments onto the acoustic track "The Sound of Silence," transforming it into a folk-rock anthem that shot to No. 1 on the American charts in 1965. The song announced something genuinely new: neither folk music nor rock and roll, it was, as the Kennedy Center describes, "an American troubadour's passionate narrative impulse filtered through an urbane aesthetic drenched in melancholy gentleness".
What followed was a remarkable run of five era-defining albums: Sounds of Silence (1966), Parsley, Sage, Rosemary and Thyme (1966), Bookends (1968), and the duo's valedictory Bridge Over Troubled Water (1970). These albums produced an extraordinary catalogue of songs that became part of the American cultural fabric: "Mrs. Robinson," "Homeward Bound," "The 59th Street Bridge Song (Feelin' Groovy)," "America," "The Boxer," "Hazy Shade of Winter," and "At the Zoo," among many others.
The partnership, however, was always fraught with tension. Garfunkel pursued an acting career, and creative differences increasingly strained their relationship. Bridge Over Troubled Water, released in January 1970, became their most successful album and won the Grammy for Album of the Year, but the duo broke up shortly after its release. They would reunite sporadically over the decades—most memorably for a legendary free concert in Central Park in 1981 that drew over 500,000 people—but the partnership was never permanently restored.
The Solo Artist: A Journey of Constant Reinvention
Simon's solo career, which began in earnest with the release of The Paul Simon Songbook in 1965 and truly took flight with his 1972 self-titled album, has been defined by relentless artistic exploration. His first post-breakup album, Paul Simon (1972), featured the reggae-inflected hit "Mother and Child Reunion," a song whose title was reportedly inspired by a chicken-and-egg dish he saw on a Chinese restaurant menu. The album also included "Me and Julio Down by the Schoolyard," a playful narrative of youthful rebellion that became one of his most enduring solo hits.
There Goes Rhymin' Simon (1973) continued his commercial and critical success, yielding the gospel-tinged "Loves Me Like a Rock," backed by the Dixie Hummingbirds, and the sardonic "Kodachrome," a buoyant shuffle that masked its meditation on memory and photography with an irresistibly catchy chorus. The album earned Simon a Grammy for Best Album of the Year, and its hit single "50 Ways to Leave Your Lover"—which Simon once dismissed as "basically a nonsense song"—became one of his biggest successes, its clever rhyming structure ("You just slip out the back, Jack / Make a new plan, Stan") embedding itself in the cultural consciousness.
Still Crazy After All These Years (1975) marked a more introspective turn, with its title track becoming one of Simon's most enduring ballads. The lonesomely lilting tune has been covered by artists from Ray Charles to Karen Carpenter, its relatable lost-in-love lyricism and moving arrangement resonating across genres. The album won Simon his second Grammy for Album of the Year as a solo artist.
The 1980s brought both challenges and triumphs. Hearts and Bones (1983), his most personal album to date, was a commercial disappointment, described as "the lowest-charting new studio album of Paul Simon's career". Yet this period of relative failure would soon give way to his most ambitious and celebrated work.
Graceland: A Revolutionary Fusion
In 1984, at a low point in his career and personal life—his marriage to Carrie Fisher was unraveling—Simon found himself captivated by a bootleg cassette of South African mbaqanga music that a friend had given him. The accordion-heavy, jazz-rhythm-driven style of "township jive" reminded him of the early rock and doo-wop records he had loved as a teenager in Queens.
Simon traveled to Johannesburg in 1985 to record with South African musicians, a decision that proved deeply controversial due to the United Nations' cultural boycott of apartheid South Africa. He worked with a remarkable array of local groups—General MD Shirinda and the Gaza Sisters, Tao Ea Matsekha, the Boyoyo Boys, and the a cappella group Ladysmith Black Mambazo—developing melodies and lyrics on top of their already-finished grooves. This process, which Simon described as building "from the rhythm up," represented a profound shift in his approach to songwriting, one that Ashley Kahn, author of Days of Miracle and Wonder, compared to hip-hop: "Start with the beat and match the words to the beat".
The resulting album, Graceland (1986), was a revelation. It fused American pop sensibilities with South African rhythms, zydeco, and a cappella singing into something entirely new. The album sold between 14 and 16 million copies worldwide and won the Grammy for Album of the Year in 1987, with the title track winning Record of the Year in 1988. It spawned classics including "You Can Call Me Al," "Diamonds on the Soles of Her Shoes," and "Under African Skies".
Simon has said that Graceland is his greatest work and that the title track is his favourite composition. The album's legacy is complex—it introduced millions of listeners to South African music and helped launch the careers of artists like Ladysmith Black Mambazo, but it also drew accusations that Simon had broken the cultural boycott. Simon maintained that he had worked with Black South African musicians who supported his efforts, and he donated royalties to educational projects in the region.
The Rhythm of the Saints and Beyond
Simon continued his exploration of world music with The Rhythm of the Saints (1990), which blended Brazilian drums and African guitars into a hypnotic, percussion-driven soundscape. Recorded with Brazilian artists including Uakti and Milton Nascimento, the album featured the evocative "The Obvious Child" and "Can't Run But". While not as commercially dominant as Graceland, it was critically acclaimed and demonstrated Simon's commitment to artistic growth rather than repeating a winning formula.
The 1990s and 2000s saw Simon continue to evolve. You're the One (2000) was his first proper album since The Rhythm of the Saints, and Surprise (2006) found him collaborating with producer Brian Eno, whose ambient and electronic sensibilities brought a new texture to Simon's songwriting. The album featured guest appearances from guitarist Bill Frisell, drummer Steve Gadd, and pianist Herbie Hancock.
So Beautiful or So What (2011) was hailed as a return to form, with songs like "Rewrite" showcasing Simon's continuing lyrical wit and melodic invention. In 2018, he released In the Blue Light, featuring reworkings of ten of his own lesser-known songs. His most recent album, Seven Psalms (2023), was a deeply spiritual, seven-part acoustic suite that many critics regarded as one of his finest late-career achievements.
Musical Style and Harmonic Innovation
Paul Simon's musical style defies easy categorization. As a songwriter, he has drawn on an extraordinary range of influences—folk, doo-wop, gospel, reggae, zydeco, South African township jive, Brazilian percussion, and American pop—yet his voice remains unmistakably his own. His best early songs, as Britannica notes, "tended to be bookish angst-ridden reveries with simple folk rock melodies and earnest, poetically ambitious (but often mannered) lyrics". Over time, his lyrics grew more elliptical and imagistic, his melodies more harmonically adventurous.
Simon's harmonic language is particularly distinctive. Music theorist James Bennighof, in his comprehensive survey of Simon's recorded output, focuses on "meter, form, and harmonic structure, examining the relationship of music and text". Bennighof notes that Simon's songs are often "synthetic" in nature: "before the words, chords, and melody are even composed, the song is conceived as a selection and assembly of disparate elements".
One of Simon's hallmarks is his willingness to embrace tonal ambiguity. In songs like "I Do It for Your Love," "the remainder of the harmony is tonally ambiguous... However, the wide variety of chord qualities provides a deep harmonic richness. As the chords tend to bear little or no relationship to one another," the effect is one of deliberate complexity and emotional depth. This approach resists the easy resolutions of conventional pop songwriting, creating instead a sense of restless inquiry that mirrors his lyrical concerns.
The "bridge" of "Bridge Over Troubled Water" exemplifies Simon's harmonic sophistication. The song begins in a bright major key, but the bridge introduces unexpected chromatic turns and a shift in tonal centre that deepens the emotional impact of the lyric. This kind of structural ambition—marrying complex harmony to accessible melody—is a hallmark of Simon's finest work.
Simon's guitar playing, while often understated, is another crucial element of his style. Rolling Stone named him one of the 100 greatest guitarists of all time in 2011. His fingerpicking patterns, particularly on songs like "The Boxer" and "Diamonds on the Soles of Her Shoes," provide a rhythmic and melodic foundation that is both intricate and immediately recognisable.
The Art of Collaboration
Collaboration has been central to Simon's career from the very beginning. The Simon & Garfunkel partnership, though turbulent, produced some of the most beloved music of the 20th century, with Garfunkel's ethereal tenor providing the perfect counterpoint to Simon's more earthbound delivery. "Their sound was something that we strived for," Simon said of the Everly Brothers, and that same pursuit of perfect vocal blend drove his work with Garfunkel.
Beyond Garfunkel, Simon has collaborated with an extraordinary range of artists. On Graceland, he worked with Ladysmith Black Mambazo, whose soaring a cappella harmonies transformed "Homeless" and "Diamonds on the Soles of Her Shoes" into something transcendent. He recorded with Los Lobos on "All Around the World or the Myth of Fingerprints," and with zydeco group Rockin' Dopsie and the Zydeco Twisters. On The Rhythm of the Saints, he collaborated with Brazilian artists Uakti and Milton Nascimento.
In 2019, Simon performed his only live collaboration with Grateful Dead singer-guitarist Bob Weir at the Outside Lands festival in San Francisco. The two had met in 1967 when Simon came to Haight-Ashbury to invite the Dead to the Monterey Pop Festival. "I knocked on the door of their house, and Bob Weir opened the door, and we've been friends ever since," Simon told the crowd. "But actually, this is our first duet!" Weir joined Simon for a rendition of "The Boxer," adding harmonies to the song's "lie-la-lie" chorus.
Simon's collaborative spirit extends to his studio work as well. His 2006 album Surprise was produced by Brian Eno, a partnership that brought a new sonic dimension to Simon's music. He has also worked with musicians as diverse as Herbie Hancock, Steve Gadd, Bill Frisell, and the Dixie Hummingbirds.
Paul Simon in Film
Simon's music has had a profound relationship with cinema, beginning with Mike Nichols' The Graduate (1967). Nichols asked Simon to write a score for the film, and the resulting soundtrack—featuring "The Sound of Silence," "Mrs. Robinson," "Scarborough Fair/Canticle," and "April Come She Will"—became inseparable from the film's iconic status. The soundtrack won a Grammy for Best Original Score Written for a Motion Picture. The use of "The Sound of Silence" during the film's climactic scene remains one of the most powerful marriages of song and image in cinema history.
Simon has 34 credits as a film composer, starting with Shampoo in 1975, and his songs have been featured in 372 movies and music videos. In 1980, he wrote, produced, and starred in One-Trick Pony, a film about a struggling musician navigating the music industry. The soundtrack album included "Soft Parachutes" and "Late in the Evening," the latter becoming a Top 10 hit.
More recently, Simon wrote "Father and Daughter" for The Wild Thornberrys Movie (2002), which earned him a Golden Globe nomination for Best Original Song. The song, a tender meditation on parental love, won a Grammy for Best Song Written for a Motion Picture, Television or Other Visual Media.
Simon has also made memorable acting appearances, including a cameo in Woody Allen's Annie Hall (1977) and a guest role on Saturday Night Live, where he famously performed "Still Crazy After All These Years" in a turkey costume—a self-deprecating moment that endeared him to a new generation of fans.
Influences and Legacy
Paul Simon's influence on popular music is difficult to overstate. As the songwriting half of Simon & Garfunkel, he helped define the youth movement of the 1960s, his literate, introspective lyrics and sophisticated melodies providing a template for generations of singer-songwriters to come. His solo work, particularly Graceland, fundamentally altered the relationship between Western pop and global music traditions, paving the way for artists from Paul Simon contemporaries to contemporary musicians like Vampire Weekend and Fleet Foxes.
His musical influences were eclectic from the start. He has cited Bob Dylan, Chuck Berry, Randy Newman, and the Everly Brothers among his formative inspirations. But Simon's genius lay not in imitation but in synthesis—the ability to absorb disparate influences and forge them into something entirely new.
Simon's legacy is enshrined in an extraordinary array of honours. He has won 16 Grammy Awards, including three for Album of the Year: Bridge Over Troubled Water (1970), Still Crazy After All These Years (1975), and Graceland (1986). He received a Grammy Lifetime Achievement Award in 2009 and was inducted into the Rock and Roll Hall of Fame as a solo artist in 2001 (having already been inducted as part of Simon & Garfunkel in 1990). In 2007, he became the first recipient of the Library of Congress's Gershwin Prize for Popular Song. He has been awarded the Kennedy Center Honors and is a member of the American Academy of Arts and Sciences.
In 2006, Time magazine named him one of the "100 People Who Shaped the World". Rolling Stone has placed him on two of its "100 Greatest of All Time" lists—as a guitarist and as a songwriter.
Philanthropy and Personal Life
Beyond music, Simon has been a dedicated philanthropist. In 1987, he co-founded the Children's Health Fund with Dr. Irwin Redlener, an organization that brings health care to low-income children and their families across the United States. He has raised millions of dollars for causes including the American Foundation for AIDS Research, the Nature Conservancy, and The Fund for Imprisoned Children in South Africa. In recent years, he has donated the proceeds from his concerts to charity, primarily those involved with children's musical education and the environment.
Simon's personal life has been marked by both joy and difficulty. He was married to Peggy Harper from 1969 to 1975, and to Carrie Fisher from 1983 to 1984. In 1992, he married singer-songwriter Edie Brickell, with whom he has three children: Adrian, Lulu, and Gabriel. His son Harper, from his first marriage, was born in 1972.
Paul Simon: The Eternal Troubadour
As Paul Simon turns 85, his place in the pantheon of American music is secure. He is that rarest of artists: a songwriter of profound commercial success who never sacrificed artistic integrity, a musician of extraordinary technical skill who never lost sight of the emotional power of a simple melody, and a cultural ambassador who opened Western ears to the riches of global music.
His songs have provided the soundtrack to countless lives—first loves and last dances, quiet moments of reflection and raucous celebrations. From the haunting opening bars of "The Sound of Silence" to the joyous rhythms of "Graceland," Simon's music has a way of embedding itself in memory, becoming part of the listener's own story.
"I believe in the future," Simon sang in "Cool, Cool River" from The Rhythm of the Saints. "We shall suffer no more / Maybe not in my lifetime / But in yours I feel sure". It is a sentiment that captures the essence of his art: a generous, hopeful vision of human possibility, expressed through melodies that linger long after the music stops. At 85, Paul Simon remains what he has always been—America's eternal troubadour, still searching, still surprising, still singing.
Discography
Main article on Wikipedia: Paul Simon discography
See also: Simon & Garfunkel discography
This discography does not include compilation albums, concert albums or work with Simon & Garfunkel. Simon's solo concert albums often have songs he originally recorded with Simon & Garfunkel, and many Simon & Garfunkel concert albums contain songs Simon first recorded on solo albums.[153][154]
Simon has a few songs that appear on compilation albums and nowhere else, such as "Slip Slidin' Away", which first appeared on the compilation album Greatest Hits, Etc. (1977) and has since been included in subsequent compilations such as Negotiations and Love Songs (1988).[155]
Solo studio albums
- The Paul Simon Songbook (1965)
- Paul Simon (1972)
- There Goes Rhymin' Simon (1973)
- Still Crazy After All These Years (1975)
- One-Trick Pony (1980)
- Hearts and Bones (1983)
- Graceland (1986)
- The Rhythm of the Saints (1990)
- Songs from The Capeman (1997)
- You're the One (2000)
- Surprise (2006)
- So Beautiful or So What (2011)
- Stranger to Stranger (2016)
- In the Blue Light (2018)
- Seven Psalms (2023)
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PAUL SIMON - Seven Of The Best
Simon & Garfunkel: Live at Shoreline 1993
Recorded live in October 1993 at the Shoreline Amphitheatre in Mountain View, California, this pristine archival performance captures Paul Simon and Art Garfunkel during their celebrated 1993 reunion run. Set against the crisp Northern California air, the duo delivers spellbinding acoustic renditions of their timeless catalog, blending Paul Simon's masterful fingerstyle guitar work with Art Garfunkel's soaring, angelic vocal melodies.
The Live Lineup:
Paul Simon – Lead Vocals, Acoustic Guitar
Art Garfunkel – Lead Vocals
5 Fast Facts About the Performance & Liner Notes:
- The Historic 1993 Reunion Era – Following their legendary 1981 Central Park concert, Simon & Garfunkel reunited in late 1993 for select benefit shows and a celebrated sold-out theater residency, reminding the world of their unmatched vocal chemistry.
- An Unrivaled Harmonic Balance – Art Garfunkel's ethereal tenor vocal lines paired with Paul Simon's rhythmic acoustic guitar and poignant lyricism created a musical blueprint that defined 1960s folk-rock and adult contemporary pop.
- The Shoreline Amphitheatre Atmosphere – Designed by Bill Graham to resemble the Grateful Dead's "Steal Your Face" logo, Shoreline's outdoor bowl provided an intimate, acoustics-friendly setting for acoustic anthems like "The Sound of Silence" and "The Boxer."
- The Show-Stopping "Bridge Over Troubled Water" – Garfunkel's solo vocal delivery on their 1970 masterpiece brought thousands of outdoor concertgoers to a complete hush before erupting into one of the night's biggest ovations.
- Soundboard Master Restoration – Sourced directly from original multi-track soundboard master tapes, this audio restoration cleanly isolates Simon's subtle guitar picking and the duo's delicate two-part vocal harmonies in high-fidelity clarity.
