20 Best Paul Simon Songs of All Time

Paul Simon is one of the most influential singer-songwriters in the history of popular music. With a career spanning over six decades, Simon has released multiple albums and produced numerous hits that continue to be beloved by fans around the world. His signature sound, which blends elements of folk, rock, and world music, has earned him critical acclaim and a devoted following. Simon’s introspective lyrics and intricate melodies have resonated with listeners for generations, making him a cultural icon and a source of inspiration for countless musicians. In this article, we will explore the best Paul Simon songs of all time, delving into their origins, significance, and why they remain timeless classics. From his early days as half of the folk duo Simon & Garfunkel to his later success as a solo artist, Simon has produced a diverse and impressive catalog of hits that showcase his incredible talent and creativity. Whether you’re a longtime fan or a newcomer to his music, this list is sure to remind you of the incredible legacy of Paul Simon and why his songs continue to be some of the most beloved and enduring in music history. So, sit back, turn up the volume, and let’s take a journey through some of the greatest Paul Simon songs ever recorded.

1. “Bridge over Troubled Water” – Bridge Over Troubled Water, 1970

“Bridge over Troubled Water” is a powerful ballad that showcases Simon & Garfunkel’s musical and vocal prowess. The lyrics speak to the comfort and support we can offer one another during difficult times. The song’s soaring chorus and tender piano melody make it a timeless classic that continues to resonate with listeners today.

2. “The Boxer” – Bridge Over Troubled Water, 1970

“The Boxer” tells the story of a struggling musician trying to make it in New York City. The song is driven by Paul Simon’s acoustic guitar and features intricate harmonies and percussion. The lyrics are poignant and introspective, exploring themes of perseverance and resilience in the face of adversity.

3. “The Sound of Silence” – Wednesday Morning, 3AM, 1964

“The Sound of Silence” is a hauntingly beautiful song that captures the feelings of loneliness and isolation that many people experience. The song’s gentle guitar melody and whispered vocals create a sense of intimacy and vulnerability that make it a timeless classic.

4. “America” – Bookends, 1968

“America” is a folk-rock masterpiece that explores the themes of wanderlust and searching for identity. The song’s vivid imagery and driving guitar rhythm make it a fan favorite and a staple of Simon & Garfunkel’s live performances.

5. “Mrs Robinson” – Bookends, 1968

“Mrs. Robinson” is a catchy and playful tune that showcases Simon & Garfunkel’s ability to write a great pop song. The song’s lyrics reference the classic movie “The Graduate” and the chorus has become a cultural touchstone.

6. “Homeward Bound” – Parsley, Sage, Rosemary & Thyme, 1966

“Homeward Bound” is a bittersweet tune that captures the feeling of homesickness and longing for connection. The song’s simple guitar melody and emotive vocals make it a standout track on “Parsley, Sage, Rosemary & Thyme.”

7. “Bookends Theme – Reprise” – Bookends, 1968

“Bookends Theme – Reprise” is a brief but haunting instrumental that serves as a bookend to the album of the same name. The song’s gentle piano melody and atmospheric sound effects create a sense of nostalgia and reflection.

8. “Old Friends” – Bookends, 1968

“Old Friends” is a tender ballad that explores the complexities of friendship and the passage of time. The song’s poignant lyrics and lush harmonies make it a standout track on “Bookends.”

9. “Scarborough Fair/Canticle” – Parsley, Sage, Rosemary & Thyme, 1966

“Scarborough Fair/Canticle” is a haunting folk song that blends traditional English ballads with contemporary lyrics. The song’s intricate vocal harmonies and haunting melody make it one of Simon & Garfunkel’s most iconic tracks.

10. “The Only Living Boy in New York” – Bridge Over Troubled Water, 1970

“The Only Living Boy in New York” is a poignant tune that explores the feeling of isolation and longing for connection. The song’s gentle guitar melody and emotive vocals make it a standout track on “Bridge Over Troubled Water.”

11. “April Come She Will” – Sounds of Silence, 1965

“April Come She Will” is a gentle ballad that captures the fleeting nature of time and the seasons. The song’s gentle guitar melody and poetic lyrics make it a standout track on “Sounds of Silence.”

12. “El Condor Pasa (If I Could)” – Bridge Over Troubled Water, 1970

“El Condor Pasa (If I Could)” is a beautiful instrumental that showcases Simon & Garfunkel’s ability to blend traditional Andean music with contemporary rock. The song’s intricate flute melody and driving guitar rhythm make it a fan favorite.

13. “I Am a Rock” – Sounds of Silence, 1965

“I Am a Rock” is a poignant and introspective song that explores the themes of isolation and emotional detachment. The song’s driving guitar rhythm and emotive vocals make it a standout track on “Sounds of Silence.”

14. “Cecilia” – Bridge Over Troubled Water, 1970

“Cecilia” is a playful and upbeat tune that showcases Simon & Garfunkel’s ability to write a great pop song. The song’s catchy chorus and infectious rhythm make it a fan favorite and a staple of their live performances.

15. “My Little Town” – Still Crazy After All These Years (Simon) and Breakaway (Garfunkel), both 1975

“My Little Town” is a bittersweet tune that explores the themes of longing and nostalgia. The song’s melancholic melody and evocative lyrics make it a standout track on both Simon and Garfunkel’s solo albums.

16. “A Hazy Shade of Winter” – Bookends, 1968

“A Hazy Shade of Winter” – Bookends, 1968: This song is a reflection of the fast pace of life and how it can leave one feeling lost. The lyrics describe the chaos and confusion of modern times and the need to adapt to survive. The use of rock instrumentation and harmonies creates a sense of urgency and anxiety that perfectly captures the mood of the song.

17. “The 59th Street Bridge Song (Feelin’ Groovy)” – Parsley, Sage, Rosemary & Thyme, 1966

“The 59th Street Bridge Song (Feelin’ Groovy)” – Parsley, Sage, Rosemary & Thyme, 1966: This song has a cheerful, upbeat melody and lyrics that celebrate the small joys of life. The use of simple acoustic guitar and vocal harmonies creates a peaceful, optimistic mood that encourages the listener to slow down and appreciate the moment.

18. “Kathy’s Song” – Sounds of Silence, 1965

“Kathy’s Song” – Sounds of Silence, 1965: This song is a tender love ballad that showcases Simon’s poetic lyrics and Garfunkel’s beautiful voice. The use of fingerpicking guitar and subtle percussion creates a peaceful, dreamy mood that perfectly matches the introspective lyrics.

19. “For Emily, Whenever I May Find Her” – Parsley, Sage, Rosemary & Thyme, 1966

“For Emily, Whenever I May Find Her” – Parsley, Sage, Rosemary & Thyme, 1966: This song is a hauntingly beautiful ballad that showcases Garfunkel’s angelic voice. The lyrics describe the search for a lost love and the longing to be reunited. The use of acoustic guitar and vocal harmonies creates a sense of intimacy and vulnerability that draws the listener in.

20. “Bleecker Street” – Wednesday Morning, 3AM, 1964

“Bleecker Street” – Wednesday Morning, 3AM, 1964: This song is a nostalgic reflection on the bohemian lifestyle of New York’s Greenwich Village in the 1960s. The use of fingerpicking guitar and Simon’s poetic lyrics create a romantic, dreamy mood that perfectly captures the spirit of the times. The harmonies of Simon and Garfunkel add a layer of sweetness and longing to the song.

Edward Tomlin

Edward Tomlin is a frequent contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us via social media below.