The 15 Best Simon & Garfunkel Songs

Amongst all the drama and bitterness between Paul Simon and Art Garfunkel, (still crazy after so many these years), the pair knew how to make music together. Before they reached their multiple breaking points, Paul and Art were childhood friends who as teenagers performed under the name Tom & Jerry. Eventually the pair settled on a new band name and honed their folk style everywhere from Greenwich Village coffee shops to European locales.

Before splitting in 1970, although they’ve reunited numerous time since, the iconic duo released five studio albums crafting traditional folk and folk-rock music. And by now, they’ve become so entrenched in popular music that practically anytime musicians harmonize and wield an acoustic guitar, the names Simon and Garfunkel come up. Despite the fact that none of their songs were officially written together, the combination of Paul’s intricate and timeless songwriting, Art’s vocals, and their voices together makes them one of the best musical duos of all time. Here are the 15 Best Simon & Garfunkel songs.

15. “Bleecker Street”
Unsuccessful when first released—so much so that they briefly disbanded—Simon & Garfunkel’s debut album Wednesday Morning, 3 A.M. reveals a politically conscious, Bob Dylan influenced folk duo on the brink of greatness. In Simon’s quick snapshot of 1960s New York City, he writes about the places he and Garfunkel frequent along with many other hopeful folk acts. “Bleecker Street” shows that even when catering to the popular style of the time, Simon & Garfunkel stand out.

14. “A Hazy Shade of Winter”
“A Hazy Shade of Winter” is one of the most rock-oriented Simon & Garfunkel songs but doesn’t lose any of Simon’s poetic charms along the way. He writes of a glum and frustrated poet whose mood has clearly been affected by a dreary winter. The delicious misery of the song hits a high point during this third verse, “Hang on to your hopes, my friend / That’s an easy thing to say / But if your hopes should pass away / Simply pretend that you can build them again” and never looks back.

13. “The 59th Street Bridge Song (Feelin’ Groovy)”
With a clear message to slow down, “you move too fast,” “The 59th Street Bridge Song (Feelin’ Groovy)” is one of the more playful Simon & Garfunkel songs. Made complete with a great walking bass line, whistling, and an air of carelessness that’s infectious, it’s hard not to feel groovy too.

12. “Cecilia”
Along with “The 59th Street Bridge Song (Feelin’ Groovy),” Simon & Garfunkel show that they can ditch the turtlenecks and get down. A percussion-filled and foremost fun song, “Cecilia” is a blessing every time it comes on the radio and forever a curse for anyone with the name Cecilia.

11. “Homeward Bound”
In his reflection on the lonely and often unfulfilling life of a touring musician, Simon also sets out the roles he and Garfunkel play in the band with the line, “every stop is neatly planned for a poet and a one-man band.” Charged by a lively rhythm not that dissimilar from a moving vehicle, “Homeward Bound” sounds like home even during the most challenging bouts of homesickness.

10. “Old Friends”
Simon has been quoted as saying that Bookends is the “quintessential Simon & Garfunkel album.” A concept album centered on the theme of ageing and with it disillusionment, side A closes with “Old Friends” and its partner “Bookends Theme.” In “Old Friends” Simon writes about two friends on a park bench “silently sharing the same fears.” The haunting sketch of everlasting friendship is backed by a dramatic strings section and, appropriately, includes the duo sharing vocal duties.

9. “Bookends Theme”
With a single note from a violin ushering it in, “Old Friends” melts into “Bookends;” and it wouldn’t be right to include one song without the other. This final track of side A is a minute and twenty seconds of simplistic beauty. The same instrumentation heard at the beginning of the record is back as Simon’s gentle guitar picking guides this meditation on aging and preserving the past.

8. “I Am A Rock”
Fifty years later and the sentiments in “I Am A Rock” are still incredibly relatable. A sullen track about how to avoid pain (answer: isolate yourself), “I Am A Rock” finds a little light thanks to the breezy guitar riff throughout but lyrics like, “I have no need of friendship, friendship causes pain” quickly casts a dark shadow once again.

7. “Scarborough Fair/Canticle”
Combining the tradition English folk ballad “Scarborough Fair” with reworked lyrics from Simon’s “The Side of a Hill” (which appeared on his 1965 solo album The Paul Simon Songbook to make “Canticle”) “Scarborough Fair/Canticle” is the band’s most dreamy number. The easy way Simon and Garfunkel’s voices weave together here is magic and shows how special their harmonies really are.

6. “The Only Living Boy In New York”
In “The Only Living Boy In New York,” a lonely Simon writes a not-so-subtle ode to Garfunkel who’s away in Mexico working on his acting debut in Catch-22. A Simon-centric song, lyrics like “Hey, I’ve got nothing to do today but smile” and “Half of the time we’re gone but we don’t know where” are more examples of his enduring poetics. In a brilliant little touch, Garfunkel pops up only faintly in the chorus to provide a dream-like presence and sings, “here I am.”

5. “Mrs. Robinson”
Arguably the duo’s most recognizable song thanks to a film called The Graduate, “Mrs. Robinson” is as wildly catchy as it is an important part of 1960s popular culture. Managing to reference The Beatles (“Koo-koo-ka-choo”) and Joe DiMaggio (“Where have you gone?”), Simon’s guitar work is also stellar while the bongo inclusion from Hal Blaine can’t go without a mention. It makes for a seductive song, indeed.

4. “The Boxer”
As a song about endurance, it is fitting that “The Boxer” remains a powerful and lasting anthem. The soft layer of sound created by Simon’s guitar is pierced by fierce beats on a snare drum that makes one of the best instrumental moments from any Simon & Garfunkel song. For a hopeful and everlasting sentiment, the song’s final line reads, “I am leaving, I am leaving / But the fighter still remains.”

3. “The Sound of Silence”
“Hello, darkness, my old friend / I’ve come to talk with you again.” Arrested Development jokes aside, this lyric from “The Sound of Silence” is one of the most iconic song openers in music. Though Simon admitted later to being inspired to write that lyric after turning off the bathroom light during a songwriting session (for the bathroom often has the best acoustics), the song is a perceptive commentary on people’s inability to communicate. Other timeless lyrics like, “And the people bowed and prayed / To the neon god they made” makes “The Sound of Silence” forever an important song in music’s history.

2. “America”
From Pittsburgh to Michigan, Saginaw, to the New Jersey Turnpike, Simon takes listeners on a road trip through the Eastern United States in “America.” Among his tale about two hopeful young travellers, he captures the anxiety that filled the 1970s. Ultimate road trip song status aside, the combination of the simple but multi-faceted narrative, folk-rock makeup, and the duo’s angelic harmonies, makes this the strongest performance from the pair together.

1. “Bridge Over Troubled Water”
An emotional masterpiece about friendship, “Bridge Over Troubled Water” is the quintessential Simon & Garfunkel song and yet, does not even feature both musicians on the studio recording. In a generous moment from Simon, one that he has stated he regrets, Garfunkel is the sole vocalist, soaring high and showing off how mighty his instrument really is while the accompanying instrumentals are provided by studio musicians. The strength of their individual talents on display is stunning, but what a mighty team they make.