As a prolific singer-songwriter for over six decades, Paul Simon has consistently demonstrated his aptitude for crafting songs that resonate with music fans. With his distinct blend of folk, pop, and world music, Simon has crafted a vast catalogue of timeless classics that continue to delight audiences to this day.

Focusing on his solo work, we’re going to delve into the best songs from Paul Simon’s unparalleled career. From his poignant lyrics to his intricate melodies, these songs showcase a true genius at work, and are a testimony to his enduring legacy in the music industry.




“Graceland” – Paul Simon

“Graceland” is an emblematic track that epitomizes Paul Simon’s prowess as a singer-songwriter. Released in 1986, the song features lively African rhythms infused with Simon’s signature lyrical style. The tune’s catchy melody and infectious beats have made it a beloved classic that continues to captivate audiences today.

With its unique blend of diverse cultural sounds, “Graceland” remains a timeless masterpiece that showcases Simon’s formidable songwriting prowess.


“The Sound of Silence” – Simon & Garfunkel

“The Sound of Silence” is a timeless classic that showcases Paul Simon’s songwriting prowess. The exquisite combination of Simon’s emotive lyrics and Garfunkel’s soulful voice, accompanied by the subdued yet intense melody, creates a hauntingly beautiful masterpiece. The lyrics are thought-provoking and evoke feelings of loneliness and despair, yet somehow, they also radiate hope.

This song captures the essence of Simon’s musical genius and continues to resonate with audiences of all ages, even after more than five decades since its original release.


“Me and Julio Down by the Schoolyard” – Paul Simon

“Me and Julio Down by the Schoolyard” is a groovy track that captures Paul Simon’s eclectic style. The song’s upbeat rhythm and playful lyrics about youthful rebellion make it an unforgettable tune. With its catchy melody and vibrant energy, it’s no wonder why this song remains a fan favorite among Simon’s repertoire.

So, if you’re looking for a funky hit that’ll get you moving and shaking, “Me and Julio Down by the Schoolyard” is definitely worth a listen.


“Bridge Over Troubled Water” – Simon & Garfunkel

“Bridge Over Troubled Water” is a classic Paul Simon track that showcases his songwriting prowess. Its emotive lyrics and haunting melody have made it a timeless piece that continues to resonate with audiences today. With its soulful vocals and iconic piano riff, this track remains a staple in Simon’s extensive catalogue of hits.

Its universal message of providing solace to those in need is as relevant now as it was when it was first released. Overall, “Bridge Over Troubled Water” solidifies Simon’s position as one of the greatest songwriters of our time.


“Mrs. Robinson” – Simon & Garfunkel

“Mrs. Robinson” ranks among the all-time greatest songs by iconic folk rock duo Simon & Garfunkel. With its playful yet haunting melody and racy lyrics, the track captured the rebellious spirit of the 1960s counterculture. Paul Simon’s masterful songwriting and Art Garfunkel’s soaring vocals make this a timeless classic that continues to captivate listeners young and old.

Whether you’re a fan of old-school folk rock or simply appreciate great music, “Mrs. Robinson” is a must-hear track that stands the test of time.


“Diamonds on the Soles of Her Shoes” – Paul Simon

This track is a groovy journey through African rhythms and storytelling lyrics; Paul Simon’s signature blend of world music and folk-rock is showcased perfectly here. The intricate guitar work and stunning vocal harmonies are reminiscent of Simon’s earlier work with Simon & Garfunkel, while the unique blend of sounds and percussion highlight his innovative and eclectic musical style.

“Diamonds on the Soles of Her Shoes” stands out as a standout track in Simon’s extensive discography, showcasing his versatility and creativity as a songwriter and musician.


“The Boxer” – Simon & Garfunkel

“The Boxer” is undoubtedly one of Paul Simon’s most iconic songs. With its haunting melody and poignant lyrics, it captures the heart and soul of a young musician struggling to make it in the big city. The song’s sweeping chorus and intricate guitar work are testaments to Simon’s formidable songwriting skills, while its themes of perseverance and hope resonate deeply with listeners of all ages. It’s a timeless classic that continues to inspire and move people some five decades after its initial release.”


“Kodachrome” – Paul Simon

When it comes to the timeless catalog of Paul Simon, one song stands out as a colorful gem: “Kodachrome.” This catchy tune encapsulates the essence of Simon’s artistry, blending infectious melodies with introspective storytelling. It’s a musical snapshot that captures the spirit of an era and invites us to embrace the joyous moments in life. Released during a period when Simon had already solidified his status as a musical legend, “Kodachrome” further cemented his place in the hearts of listeners. Its lyrics speak of nostalgia and the power of capturing life’s precious moments through the lens of a camera.

“Homeward Bound” – Simon & Garfunkel

“Homeward Bound” is an exquisite tune by Paul Simon, filled with the many complexities that make his songs stand out. The addictive melody and Simon’s poetic lyrics create a burst of emotions that are sure to leave listeners in a state of awe. It’s a beautiful example of Simon’s lyrical genius and knack for crafting timeless classics.

With its heart-melting melody and emotionally charged lyrics, “Homeward Bound” is undoubtedly one of Simon’s best works that can be enjoyed by music lovers of all generations.


“Slip Slidin’ Away” – Paul Simon

“Slip Slidin’ Away”, a melancholic and insightful ballad, exemplifies the introspective style that Paul Simon is revered for. The song explores the ephemeral nature of life and relationships, utilizing vivid imagery to convey a sense of fleetingness and uncertainty. The poignant lyrics are matched by a haunting melody, creating a haunting effect that leaves a lasting impression on listeners.

The song showcases Simon’s ability to craft introspective lyrics that resonate with audiences of all ages, making it a worthy addition to any list of his greatest hits.


“America” – Simon & Garfunkel

“America” from Paul Simon’s time with Simon & Garfunkel offers a wistful account of youthful wanderlust and the American dream. The track pulses with a sense of possibility, as the lyrics pair breathtaking descriptions of stunning vistas with a desire to explore the world. The song captures the restless energy and yearning for adventure that characterizes much of Simon’s finest work, making it an essential entry in any “best songs” list.

An upbeat tempo and catchy melodic hooks add to the song’s appeal, making it a standout on the album and a timeless classic in the folk-rock canon.


“Still Crazy After All These Years” – Paul Simon

“Still Crazy After All These Years” is a timeless classic that showcases Paul Simon’s poetic songwriting style. Released in 1975, the song explores the complexities of relationships and the ever-changing nature of love. Simon’s use of vivid metaphors and clever wordplay create a sense of intrigue that keeps listeners engaged from start to finish.

The track’s infectious melody, coupled with Simon’s signature vocal delivery, makes it a standout hit and one of the best songs in his extensive catalog of music. It’s a true masterpiece that continues to resonate with audiences of all ages.


“Cecilia” – Simon & Garfunkel

Let’s talk about Simon & Garfunkel’s “Cecilia.” This rhythmic, percussive song finds Paul Simon singing about a turbulent relationship and the frustrations that come with it. With its anthemic “dum dum dum” chorus, “Cecilia” has become a fan favorite over the years and a staple of Simon’s live shows. The song’s infectious energy and catchy melody make it one of Simon’s best-known hits and an essential addition to any playlist of his greatest songs.



“50 Ways to Leave Your Lover” – Paul Simon

“50 Ways to Leave Your Lover” is an enigmatic tune that’s both infectious and evocative. It’s a timeless classic that showcases Paul Simon’s songwriting prowess and musical ingenuity. The song’s playful melody belies the earnest lyrics; Paul Simon delicately addresses the sensitive topic of breaking up with someone in a deceptively upbeat manner.

The song features a dynamic and diverse arrangement that incorporates different instruments and soundscapes, making it a unique and multifaceted piece of music. Overall, “50 Ways to Leave Your Lover” is one of the finest examples of Paul Simon’s musical genius.


“The Only Living Boy in New York” – Simon & Garfunkel

“The Only Living Boy in New York” is a musing track that dwells in melancholy and introspection. Brimming with contemplative lyrics and soothing harmonies, this offering from Simon & Garfunkel is one of their most enigmatic releases. The song feels like a soliloquy, with Simon’s warm voice taking center stage and inviting the listener to delve into their own thoughts and emotions. It’s a beautifully crafted piece of music that captures the essence of Paul Simon’s introspective songwriting style with grace and finesse.


“Late in the Evening” – Paul Simon

“Late in the Evening” is a groovy tune that encapsulates the energy and soul of Paul Simon’s music. The rhythmic beat, juxtaposed with the jazzy horns and catchy lyrics, creates a memorable experience for listeners. Simon’s distinct voice and the vibrant instrumentation make this an essential track in his repertoire that continues to resonate with fans.

The song showcases the diverse musical influences that Simon seamlessly weaves together in his work, making it a must-listen for fans of classic rock, world music, and everything in between.


“Scarborough Fair/Canticle” – Simon & Garfunkel

“Scarborough Fair/Canticle” is a captivating masterpiece that embraces the essence of Paul Simon’s storytelling. Its haunting melody and potent lyrics evoke a sense of longing and bittersweet nostalgia. The song merges Simon’s original composition with an old traditional ballad and interweaves the two into a tapestry of beauty.

It’s a true marvel of songwriting that’s as timeless today as it was when it was released. If you’re looking for a quintessential Paul Simon song, this one is an absolute must-listen.


“I Know What I Know” – Paul Simon

“I Know What I Know” is an enthralling composition by Paul Simon that showcases his virtuosity as a songwriter. The track incorporates a captivating fusion of African rhythms, percussive beats, and soulful vocals, creating a dynamic and visceral listening experience. With its contagious energy and enigmatic lyrics, “I Know What I Know” stands out as a standout track in Simon’s vast and illustrious catalogue, solidifying his reputation as one of the greatest songwriters of all time.


“The Dangling Conversation” – Simon & Garfunkel

With its hauntingly beautiful melody and thought-provoking lyrics, this Simon & Garfunkel classic delves into the complexities of human relationships and the difficulty of truly understanding each other’s perspectives. The intricately woven harmonies and delicate finger-picking patterns create a sense of intimacy and vulnerability that draws the listener in and leaves them pondering the song’s meaning long after the last chord has faded away. It’s no wonder why this track is often considered one of Paul Simon’s greatest compositions.


“Call Me Al” – Paul Simon

“Call Me Al” is premier Paul Simon song that exudes vivacity, without scrimping on depth and meaning. It swings with an upbeat rhythm that captures listeners from the first note and carries them through an enjoyable and lively musical journey. The lyrics weave intricate facial imagery into the song, showcasing Simon’s literary prowess. From the playful horn section to the catchy chorus, “Call Me Al” is undoubtedly one of Paul Simon’s best songs.


“The 59th Street Bridge Song (Feelin’ Groovy)” – Simon & Garfunkel

The groovy and upbeat “59th Street Bridge Song” by Paul Simon is a classic tune that captures the essence of the free-spirited 1960s. With catchy lyrics and a cheerful melody, this song is sure to put a smile on your face and a spring in your step. Its playful and carefree tone makes it a standout tune in Simon’s impressive repertoire, and a must-listen for any fan of his music.


“Mother and Child Reunion” – Paul Simon

“Mother and Child Reunion” is a fabulous tune that showcases Paul Simon’s distinctive style. The song is a fusion of the Jamaican rocksteady and American pop, creating a unique and innovative sound that’s mesmerizing to the ears. The lyrics touch on themes of loss, death, and hope, bringing up emotions and sentiments that strike a chord with anyone who’s ever gone through tough times.

Paul Simon’s voice is emotive and expressive, delivering the lyrics with power and clarity. Overall, “Mother and Child Reunion” is a masterpiece that exemplifies Paul Simon’s brilliance and artistry.


“For Emily, Whenever I May Find Her” – Simon & Garfunkel

“For Emily, Whenever I May Find Her” is a hauntingly beautiful ballad from Simon & Garfunkel’s album “Parsley, Sage, Rosemary and Thyme”. Paul Simon’s lyrics are poetic and enigmatic, perfectly complementing Art Garfunkel’s angelic voice. The song’s ethereal quality and timeless appeal make it a standout among Paul Simon’s many classic compositions.


“Loves Me Like a Rock” – Paul Simon

“Loves Me Like a Rock” is a gospel-inspired track that showcases Paul Simon’s musical versatility. This upbeat and catchy song features soulful vocals and percussion, giving it a unique sound that sets it apart from his other tracks. It’s a crowd-pleaser that’s sure to get your toes tapping and your head nodding along to the beat. With its infectious energy and memorable chorus, “Loves Me Like a Rock” is definitely a standout song in Paul Simon’s repertoire.


“A Hazy Shade of Winter” – Simon & Garfunkel

“A Hazy Shade of Winter,” with its uptempo rhythm and raw, infectious energy, showcases Paul Simon’s mastery of clever lyrical and musical arrangements. The song’s propulsive bass line stands out, while its alternation between major and minor chords creates a sense of vibrant dissonance that fits perfectly with its apocalyptic lyrics.

The imagery of “frosty mornings” and “days of future past” lends a haunting quality to Simon’s tale of youthful disillusionment. It’s a timeless classic that still sounds as fresh and invigorating today as it did when it was first released.