Paul Simon stands as one of the most influential songwriters in music history, crafting timeless melodies that have resonated across generations. From his groundbreaking work with Art Garfunkel to his innovative solo career that spanned five decades, Simon’s musical genius has produced an extraordinary catalog of songs that blend folk, rock, world music, and introspective storytelling. His ability to weave complex narratives with memorable hooks has earned him 16 Grammy Awards and a permanent place in the Rock & Roll Hall of Fame. In this comprehensive guide, we explore the 20 best Paul Simon songs that showcase his unparalleled artistry, including selections from his recent 2023 release, Seven Psalms.
The Sound of Silence
The haunting melody that launched Simon & Garfunkel into stardom remains one of the most iconic songs in popular music history. Originally released on their 1964 debut album “Wednesday Morning, 3 A.M.,” the song initially flopped until producer Tom Wilson added electric instruments without the duo’s knowledge, transforming it into a counterculture anthem. The song’s exploration of alienation and lack of communication in modern society struck a profound chord with 1960s audiences and continues to resonate today. Its poetic imagery about “darkness” and “silence” creates a meditation on human disconnection that feels as relevant in the digital age as it did during the Vietnam War era.
Bridge Over Troubled Water
This gospel-inspired masterpiece represents the pinnacle of Simon & Garfunkel’s collaboration and became one of the best-selling albums of all time. Simon wrote this song as a gift to Art Garfunkel, whose soaring vocals transformed it into an emotional powerhouse that won multiple Grammy Awards including Record of the Year and Song of the Year in 1971. The song’s message of unwavering support and friendship during difficult times has made it a staple at weddings, funerals, and moments of national healing. Its orchestral arrangement and Garfunkel’s angelic delivery combine to create a transcendent listening experience that showcases Simon’s ability to write hymn-like compositions with universal appeal.
You Can Call Me Al
From his groundbreaking 1986 album “Graceland,” this infectious track became an international sensation and helped introduce American audiences to South African music. The song features a memorable bass line performed by Bakithi Kumalo and a distinctive pennywhistle solo that became one of the most recognizable elements in Simon’s entire catalog. The accompanying music video starring Chevy Chase lip-syncing to the song while Simon appears annoyed became an MTV classic and helped propel the track to the top of the charts. The song’s narrative about a middle-aged man experiencing an identity crisis resonates with listeners questioning their place in the world, all set to an irresistibly upbeat rhythm.
50 Ways to Leave Your Lover
Paul Simon’s only solo number-one hit on the Billboard Hot 100 emerged from an unlikely source: a playful rhyming game with his young son Harper. Written following his divorce from first wife Peggy Harper, the song takes a surprisingly lighthearted approach to relationship dissolution with its catchy internal rhymes like “Slip out the back, Jack” and “Make a new plan, Stan.” The distinctive drum pattern played by Steve Gadd became one of the most studied and imitated rhythms in popular music. Despite its upbeat melody, the song captures the complex emotions of ending a relationship while maintaining a sense of humor about the situation.
Mrs. Robinson
Originally written for the landmark 1967 film “The Graduate,” this song became Simon & Garfunkel’s biggest hit and won them their first Grammy Award for Record of the Year. The song perfectly captured the disillusionment of 1960s youth culture while serving as a character study of a disillusioned suburbanite engaging in an affair with a college graduate. Its famous reference to Joe DiMaggio reflects Simon’s nostalgia for American heroes and simpler times. The song’s association with “The Graduate” cemented its place in cultural history, as both the film and song became defining artifacts of their generation.
Graceland
The title track from Simon’s most commercially successful solo album represents a journey both literal and metaphorical to Elvis Presley’s Memphis home. Featuring Forere Motloheloa’s distinctive accordion work and South African musical influences, the song addresses themes of pilgrimage, redemption, and the search for meaning following Simon’s second divorce. The track’s innovative fusion of American folk-rock with South African township music created a new sound that influenced countless artists. Despite controversy surrounding Simon’s decision to record in apartheid-era South Africa, “Graceland” became recognized as one of the greatest albums of all time and introduced millions of Western listeners to African music.
The Boxer
This epic ballad from the 1970 album “Bridge Over Troubled Water” stands as one of Simon’s most ambitious compositions, taking over 100 hours to record. The song’s narrative follows a poor boy from New York City struggling to survive, serving as both a literal character study and a metaphor for Simon’s own experiences in the music industry. The memorable “lie-la-lie” chorus and the thunderous drum sound recorded in a church hallway create an unforgettable sonic landscape. The song’s themes of perseverance in the face of adversity and the inability to escape one’s past continue to inspire listeners decades after its release.
Still Crazy After All These Years
The title track from Simon’s 1975 album became one of his most covered songs, with interpretations by Ray Charles, Frank Sinatra, and Willie Nelson among others. Written about encountering an old lover, the song captures the bittersweet nature of nostalgia and the realization that some patterns in our lives never truly change. Simon’s jazz-influenced arrangement features sophisticated chord progressions that showcase his musical maturity beyond his folk-rock roots. The song won the Grammy Award for Best Pop Vocal Performance and helped establish Simon as a serious solo artist separate from his partnership with Garfunkel.
Me and Julio Down by the Schoolyard
This infectious track from Simon’s 1972 self-titled album features one of pop music’s great unsolved mysteries: what exactly did “Mama Pajama” see? Simon himself has admitted he never decided what the inciting incident was, allowing listeners to fill in the blanks with their imagination. The song’s bouncing rhythm and horn arrangement create an irresistibly upbeat atmosphere that contrasts with the suggestion of juvenile delinquency in the lyrics. Its playful nonsensical quality demonstrates Simon’s understanding that not every song needs to deliver a clear message to connect with audiences emotionally.
America
This poignant ballad from the 1968 album “Bookends” captures the restlessness and searching quality of 1960s American youth through the story of a young couple hitchhiking across the country. The song’s imagery of counting cars on the New Jersey Turnpike and looking for America serves as a meditation on identity, belonging, and the elusive nature of the American Dream. Simon’s acoustic guitar work and Garfunkel’s harmonies create an intimate soundscape that makes listeners feel like fellow travelers on this journey. The song has been embraced by multiple generations as an anthem for those seeking meaning and connection in an increasingly fragmented society.
Diamonds on the Soles of Her Shoes
Opening the “Graceland” album, this collaboration with South African vocal group Ladysmith Black Mambazo announced that listeners were entering unprecedented musical territory. The song begins with an a cappella section sung entirely in Zulu before transitioning into Simon’s English verses about a poor boy and a rich girl. The intricate polyrhythms and layered vocal harmonies create a rich tapestry of sound that rewards repeated listening. The track’s joyful energy and innovative production techniques helped redefine what was possible in popular music by seamlessly blending diverse cultural influences.
Kodachrome
This nostalgic ode to color photography from the 1973 album “There Goes Rhymin’ Simon” became one of Simon’s biggest solo hits despite being banned by some radio stations who mistook it for commercial advertising. The song’s opening line “When I think back on all the crap I learned in high school” resonated with listeners who questioned the value of traditional education. Its bouncing melody and bright arrangement perfectly capture the sunny, saturated quality of Kodachrome film itself. The song celebrates memory, youth, and the way photography helps us hold onto moments that would otherwise fade into the past.
Late in the Evening
From the soundtrack to Simon’s 1980 film “One Trick Pony,” this upbeat track features an irresistible Latin-influenced rhythm and intricate horn arrangements. The song’s infectious groove makes it impossible to sit still while listening, showcasing Simon’s ability to craft dance-floor-ready music without sacrificing lyrical sophistication. Its autobiographical lyrics trace the development of Simon’s love for music from childhood through adulthood. Despite the commercial failure of the film itself, “Late in the Evening” reached number six on the charts and earned Simon a Grammy nomination.
Loves Me Like a Rock
This gospel-influenced track featuring the Dixie Hummingbirds became Simon’s third top-five solo hit and remains one of his most soulful compositions. The song celebrates maternal love with warmth and humor, using the metaphor of solid rock to represent unwavering support and acceptance. The powerful vocal interplay between Simon and the gospel group creates an authentic spiritual feeling that transcends religious boundaries. Its message about the enduring nature of a mother’s love has made it a favorite for Mother’s Day celebrations and family gatherings.
The Only Living Boy in New York
This farewell song to Art Garfunkel addresses the dissolution of Simon & Garfunkel’s partnership as Garfunkel pursued an acting career. The title references Garfunkel’s departure to Mexico to film “Catch-22,” leaving Simon alone in New York City. Despite the sadness underlying the lyrics, the song’s soaring arrangement and multi-tracked vocals create an uplifting atmosphere that celebrates their friendship even as it acknowledges their diverging paths.
Mother and Child Reunion
Simon’s first solo single after the Simon & Garfunkel breakup marked one of the earliest instances of a white American artist successfully incorporating reggae into mainstream pop music. Recorded in Kingston, Jamaica, a full year before Bob Marley’s breakthrough, the song’s title came from a chicken-and-egg dish Simon saw on a Chinese restaurant menu. Written after the death of his dog, the song addresses themes of loss and the hope for reunion in the afterlife. Its innovative use of Jamaican musical styles opened doors for reggae’s eventual mainstream acceptance and demonstrated Simon’s willingness to take creative risks.
Slip Slidin’ Away
This contemplative track from the “Greatest Hits, Etc.” compilation addresses the universal experience of time passing and dreams remaining unfulfilled. Each verse tells the story of different characters—a man traveling to his lover, a woman leaving an abusive relationship, a father estranged from his child—all united by the recognition that life often takes us further from our intended destinations. The song’s melancholic melody and philosophical lyrics create a meditation on mortality and the human condition. Despite its somber themes, the song provides comfort through the acknowledgment that everyone experiences this sliding away from certainty.
Duncan
From the 1972 self-titled album, this narrative song tells the story of a fisherman’s son from Lincoln, Nebraska who loses his virginity to a Pentecostal street preacher. The song’s vivid storytelling and detailed characterization showcase Simon’s literary approach to songwriting. Its fingerpicked guitar arrangement and gentle melody create an intimate atmosphere that draws listeners into Duncan’s journey of self-discovery. The song demonstrates Simon’s ability to find universal meaning in specific, quirky details and his skill at creating fully realized characters within the confines of a three-minute pop song.
Homeward Bound
Written while waiting at a British railway station during Simon & Garfunkel’s early touring days, this song captures the exhaustion and homesickness that comes with constant travel. The song’s yearning quality and simple acoustic arrangement create an achingly beautiful portrait of loneliness on the road. Its themes of seeking comfort and familiarity while pursuing dreams resonate with anyone who has felt torn between ambition and the desire for home. The song became one of Simon & Garfunkel’s signature tracks and remains a favorite among travelers and musicians who understand the emotional toll of pursuing their passions.
My Professional Opinion (from Seven Psalms)
From Simon’s 2023 release “Seven Psalms,” this track showcases the humor and wisdom of an 81-year-old artist still creating vital music. The song opens with the witty line “Good morning Mr. Indignation / Looks like you haven’t slept all night / In my professional opinion / Go back to bed and turn off your light,” demonstrating that Simon’s sharp lyrical wit remains intact. The acoustic arrangement features intricate guitar work that highlights Simon’s continued mastery of his instrument despite hearing loss during the album’s creation. This movement from the seven-part composition proves that Simon’s creative powers extend well into his ninth decade.
Frequently Asked Questions
What is Paul Simon’s most famous song?
“The Sound of Silence” and “Bridge Over Troubled Water” are generally considered Paul Simon’s most famous songs, though “You Can Call Me Al” became his biggest international solo hit. “Bridge Over Troubled Water” won multiple Grammy Awards and became one of the best-selling albums of all time, while “The Sound of Silence” defined the 1960s counterculture movement and continues to be widely recognized across generations.
Did Paul Simon release new music recently?
Yes, Paul Simon released “Seven Psalms” in May 2023, a 33-minute continuous composition divided into seven movements. This acoustic work came to Simon in dreams and represents his most meditative and spiritual project, featuring intimate guitar work and contemplations on mortality, faith, and existence despite the artist’s hearing loss during its creation.
What is Paul Simon’s only number-one solo hit?
“50 Ways to Leave Your Lover” is Paul Simon’s only solo number-one hit on the Billboard Hot 100. Released in 1975, the song topped the charts with its catchy rhyming patterns and distinctive drum work by Steve Gadd, becoming one of his most enduring solo compositions.
Why was Graceland controversial?
“Graceland” sparked controversy because Paul Simon recorded the album in South Africa during the apartheid era, which some viewed as violating the cultural boycott. However, Simon defended his decision by arguing that he collaborated with Black South African musicians and helped bring international attention to their music, ultimately contributing to the anti-apartheid movement by showcasing the country’s rich musical culture.
What inspired Paul Simon to write Seven Psalms?
Paul Simon revealed that “Seven Psalms” came to him in a series of dreams beginning in 2019, with lyrics and melodies appearing during early morning hours between 3:30 and 5 a.m. The seven-movement work was inspired by King David’s Psalms and represents Simon’s contemplation of mortality, spirituality, and the search for meaning in his ninth decade of life.
How many Grammy Awards has Paul Simon won?
Paul Simon has won 16 Grammy Awards throughout his career, including three Album of the Year awards. His honors include awards for both his work with Art Garfunkel in Simon & Garfunkel and his solo career, recognizing his profound impact on popular music over more than six decades.