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15 Best Paul Simon Songs of All Time (Greatest Hits)

July 19, 2023
Best Paul Simon Songs

Get ready to embark on a musical journey through the remarkable career of one of the most influential singer-songwriters of our time, Paul Simon.

With a rich discography spanning several decades, Paul Simon has captivated audiences around the world with his poetic storytelling, introspective lyrics, and eclectic musical style.

In this article, we will delve into the 15 best songs ever crafted by this iconic and visionary artist.

From his early days as one-half of the legendary duo Simon & Garfunkel to his successful solo career, Paul Simon has consistently pushed the boundaries of popular music, blending genres such as folk, rock, world music, and more.

His songs resonate with listeners on a deep level, addressing themes of love, introspection, societal issues, and the human experience.

So, let’s dive in and explore the best Paul Simon songs!

1. “Bridge Over Troubled Water”

Paul Simon and Garfunkel’s iconic ballad “Bridge Over Troubled Water” has become a classic, offering comfort and hope through its comforting lyrics and soothing melody.

The song, released in 1970 as the titular track of Simon and Garfunkel’s fifth and final studio album, resonates with listeners even today.

The song is based on the idea of providing comfort to someone in need, being a bridge of solace over troubled waters.

Its simple structure and arrangement, coupled with its meaningful lyrics, make it a timeless piece of music that continues to bring joy and comfort to those who need it most.

2. “The Boxer”

The Boxer” by Paul Simon is a profound composition that beautifully encapsulates the weight of worldly struggles through heartfelt lyrics and a soothing melody.

Simon’s poignant portrayal of life’s challenges resonates deeply, allowing listeners to empathize with the emotional burden carried by the song’s protagonist.

The delicate fusion of piano and strings in the instrumentation further enhances the message, providing a captivating backdrop that intensifies the somber atmosphere.

As a timeless classic, “The Boxer” possesses an enduring quality that ensures its relevance for generations to come.

It’s impactful message and brilliant composition solidify its position as one of Paul Simon and Garfunkel’s greatest musical achievements, leaving an indelible mark on the hearts and minds of listeners.

3. “The Sound of Silence”

The hauntingly beautiful “The Sound of Silence” captures the essence of loneliness and isolation like no other song.

Written by Paul Simon and released in 1964, “The Sound of Silence” became a chart-topping hit and one of his most iconic songs.

The lyrics tell a story of a man who’s been disconnected from the world, feeling unable to express himself to others.

The song’s melancholic melody and sparse instrumentation further evoke feelings of sadness, resignation, and distance.

The song has been covered multiple times and has been referred to as one of the most iconic and influential folk rock songs of all time.

4. “America”

“America” has been home to some of the most iconic songs of all genres, such as Paul Simon and Garfunkel’s Timeless.

One of the most beloved of these is his song “America”, a reflection on the beauty and the complexity of his home country.

The song explores the paradox of the land of the free, and how people can simultaneously love it and hate it.

Simon and Garfunkel’s lyrics are beautifully crafted, painting a picture of “America” that is both heartbreaking and hopeful.

The song has become a classic, and its themes are still relevant today, making it one of the best Paul Simon songs of all time.

5. “Mrs. Robinson”

You can’t think of Paul Simon and Garfunkel without remembering his hit song “Mrs. Robinson”.

It’s a tune that captures the confusion of a generation.

The song’s lyrics explore the emotions of a young man in the midst of change.

It’s a time when he’s trying to figure out who he is and where he fits in the world.

Simon’s lyrics are both witty and insightful, and the melody is catchy and memorable.

“Mrs. Robinson” is a timeless classic that has been covered by numerous artists and is still popular today.

It’s a testament to Simon and Garfunkel’s brilliance as a musician and a songwriter.

6. “Homeward Bound”

“Homeward Bound” is an inspirational folk-rock ballad that captures the hopefulness of returning home after being away for a long time.

Written by Paul Simon and Garfunkel released in 1966, the song has a wistful tone as Simon sings about his desire to return home and be reunited with his loved ones.

Musically, the song is driven by a gentle yet uplifting acoustic guitar melody and Simon’s emotive vocal performance.

Overall, “Homeward Bound” is a classic Paul Simon song that is sure to bring a smile to listeners’ faces and a tear to their eyes.

7. “Old Friends”

Leaving the bittersweet nostalgia of “Homeward Bound” behind, Paul Simon and Garfunkel’s “Old Friends” is a touching tribute to the people who’ve been in his life for years.

Through its lyrics, Simon celebrates the importance of maintaining old relationships, and the comfort they bring.

The song’s acoustic guitar and cello arrangement provide a warm and intimate setting, while Simon’s vocals convey a feeling of contemplation and nostalgia.

This line serves as a reminder of the long-lasting bond between Simon and Garfunkel, and the music they made together.

As a true classic of Simon and Garfunkel’s catalog, “Old Friends” is a timeless reminder of the value of old relationships.

8. “The Only Living Boy In New York”

Take a stroll down memory lane with Paul Simon and Garfunkel’s classic hit, “The Only Living Boy In New York”, a heartfelt tribute to the people who’ve impacted his life.

Released in 1970, “The Only Living Boy In New York” is a reflective piece about the importance of strong relationships and the power of nostalgia.

The song speaks to the universal experience of growing up and feeling alone in a big city, while at the same time reminiscing about simpler times.

The song also features a gentle and melancholic melody that’s complemented by Simon’s signature twangy vocal delivery.

With its stirring lyrics and captivating delivery, “The Only Living Boy In New York” is a timeless classic that’ll continue to resonate with listeners for generations to come.

9. “April Come She Will”

Filled with a sense of bittersweetness, Paul Simon and Garfunkel’s “April Come She Will” is a gentle ode to the passing of time.

The song is a reflection on the eternal cycle of life, with a focus on the way things change and how quickly time passes.

The lyrics are simple yet powerful, providing an uplifting message of hope as Simon expresses his appreciation for the beauty of life.

The melody is gentle and light, with a light touch of nostalgia.

The song’s structure is simple but effective, and the instrumentation is sparse yet effective.

Overall, “April Come She Will” is a timeless classic from one of the greatest singer-songwriters of all time.

10. “El Condor Pasa (If I Could)”

You can’t help but be moved by Paul Simon and Garfunkel’s classic hit, “El Condor Pasa (If I Could)”.

With its gentle melody and poetic lyrics, it’s a beautiful song that speaks to the longing for freedom and a better life.

The song has a unique structure, alternating between two different melodies.

This gives the song a dream-like quality and adds to the uplifting feel of the song.

The lyrics are filled with imagery, painting a vivid portrait of a majestic bird flying high in the sky looking for freedom.

Its simple yet profound message of hope and optimism has resonated with generations of listeners.

This has made it one of Paul Simon and Garfunkel’s most beloved classics.

11. “I Am A Rock”

With its bleak atmosphere and melancholic lyrics, Paul Simon and Garfunkel’s “I Am A Rock” is a powerful anthem of isolation and loneliness.

The song’s lyrics tell the story of a person who’s decided to protect themselves from the pain of rejection and heartache by shutting themselves off from the outside world.

Musically, “I Am A Rock” features a simple, yet hauntingly effective melody, along with sparse instrumentation that emphasizes the feeling of loneliness described in the lyrics.

The track is considered one of Paul Simon and Garfunkel’s greatest works, and it’s still frequently performed today.

12. “Cecilia”

Pulsing with vivid energy, Paul Simon and Garfunkel’s “Cecilia” is an uplifting and joyous ode to the power of love.

The upbeat folk-rock melody and catchy chorus serve as the perfect backdrop for Simon and Garfunkel’s sincere lyrics that evoke a sense of romance and nostalgia.

The song’s imagery of beautiful moments and people, such as a rambunctious celebration or the titular “Cecilia”, captures the essence of being in love and emphasizes the importance of cherishing every moment.

The song also features some of Simon’s signature wordplay and clever rhymes, further adding to its appeal.

“Cecilia” is a timeless classic and a testament to the timelessness of love.

13. “My Little Town”

Experience a nostalgic journey with Paul Simon and Garfunkel’s “My Little Town”, a beautiful reflection on the power of memories.

This classic hit, released in 1975, was co-written by Simon and his former writing partner Art Garfunkel and appeared on their final album Still Crazy After All These Years.

The song features a simple, but mesmerizing melody, with Simon’s signature tender vocal delivery.

The lyrics are a heartfelt ode to the memories of childhood, and the bittersweet feeling of growing up.

With its timeless lyrics and gentle sound, “My Little Town” has become a classic staple of the Simon and Garfunkel songbook, and is a must-have for any fan of the duo’s work.

14. “A Hazy Shade of Winter”

An anthem for anyone who’s ever felt overwhelmed by the complexities of life, Paul Simon and Art Garfunkel’s “A Hazy Shade of Winter” captures the beauty of embracing the unknown.

This 1966 classic is an exploration of life’s journey, of taking each day one step at a time.

Its upbeat tempo and rousing chorus are a reminder that even when life seems uncertain, we can make our way through with a bit of optimism and faith.

The message of “A Hazy Shade of Winter” is one of resilience, of facing the unknown with courage and determination.

It’s a timeless classic that’ll remain relevant for generations to come.

15. “Kathy’s Song”

Paul Simon and Garfunkel’s “Kathy’s Song” is a deeply moving composition that skillfully conveys the profound emotions associated with the complexities of relationships and the inescapable reality of parting.

Within the song, one can distinctly sense the rawness of Simon’s sentiments, as he navigates the bittersweet terrain of reminiscence and wistfulness.

Through his poignant reflections, he gracefully encapsulates the beautiful moments he once shared with Kathy, juxtaposing them with the somber acknowledgment of their inevitable separation.

As “Kathy’s Song” unfolds, it serves as a poignant testament to the fragile and intricate nature of human connections.

It artfully reminds us of the transitory essence of existence and the perpetual shifts that accompany our journey through life.

Simon’s evocative lyrics and soul-stirring melodies combine to create a stirring composition that resonates deeply with listeners, reminding us of the profound impact that relationships and their subsequent endings can have on our hearts.

Best Paul Simon Songs – Final Thoughts

You can’t talk about Paul Simon and Garfunkel’s music without mentioning his greatest hits.

These 15 songs are some of the best of all time, and they’ve had an impact on both popular and folk music.

Whether you’re a fan of folk, rock, or pop, there’s something here for everyone.

From “Bridge Over Troubled Water” to “My Little Town”, Paul Simon has created music that will last for generations.

So whether you’re just discovering his music today or you’ve been a fan for years, these are the songs that show why Paul Simon is one of the most influential and beloved singer-songwriters of all time.

You may also like: Best Folk Songs Ever Made

Will Fenton

Will, the founder of MIDDER, is a multifaceted individual with a deep passion for music and personal finance. As a self-proclaimed music and personal finance geek, he has a keen eye for futuristic technologies, especially those that empower creators and the public.

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