Simon and Garfunkel Songs: 15 Top Tunes

Though their relationship has grown less harmonious through the years, there’s no denying that Simon and Garfunkel's songs remain some of the best to come out of the 60s and 70s.

“This is my oldest friend, and we experienced anonymity, and then great fame and success, and those things have their own pressure," Simon, now 82, recently revealed about Garfunkel, also 82, in the MGM+ documentary In Restless Dreams: The Music of Paul Simon. “That was a good friendship. That was a real first friendship of somebody that got it. For me, to turn into a person that I hope I never see again — that’s a long way.”

Diverging career paths — Garfunkel began exploring acting, creating a more pronounced “uneven partnership” that started before their Bridge Over Troubled Water album — seemed to be the final straw for Simon, who points to Garfunkel’s film goals and their failure to communicate as the “recipe for the breakup of Simon & Garfunkel,” which came in 1970.

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Still, at their peak, the childhood friends teamed up to create what the Rock & Roll Hall of Fame — to which they were inducted in 1990 — called “celestial harmonies and finely crafted songs [that] defined a generation.”

In his induction speech, friend and contemporary James Taylor noted how “they gave me the feeling that there was very little that couldn’t be done musically. They really opened up a lot of territory. Their records were so musical and so…carefully and intricately produced. They focused so much on it. You could feel so much energy and so much thought behind [their songs].”

The duo, who grew up just three blocks from one another and played as Tom & Jerry as teens, would go on to release three No. 1 Billboard hits and win seven Grammys. Writing for Rolling Stone, which placed the duo at No. 40 on their 100 Greatest Artists list, Taylor noted that “they scored some of the most meaningful years of our lives.… Paul Simon has just always been one of our best songwriters…and Art Garfunkel is one of those great, rare voices. I would know it anywhere at the drop of a hat, in half a bar.”

Though the artists are unlikely to reunite these days — as they did so famously in Central Park in 1981, thrilling more than 500,000 fans — Simon and Garfunkel songs still prove to be as timeless as the emotions they stir in all who listen to them. Here, a look at some of the best Simon and Garfunkel songs from their complicated but inspired partnership.

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15. “My Little Town” (1975): Simon and Garfunkel songs

This tune came years after Simon and Garfunkel ventured off to pursue their own careers, but they re-teamed on this impressive track and included “My Little Town” on both their solo albums in 1975. “It’s sweet stuff in a careful way that fits the lyric,” Art Garfunkel told American Songwriter of the tune, which hit No. 1 on Billboard’s Adult Contemporary chart and earned them a Grammy nomination. “It’s a little bit dark, yeah. It’s bitter. It’s about how unimaginative [the people] were, where I come from,” Garfunkel noted of the song’s theme.

14. “The 59th Street Bridge Song Song (Feelin’ Groovy)” (1971)

Even though this song always has us and other fans, well, feelin’ groovy, Paul Simon revealed to Stephen Colbert that it has the opposite effect on him. “I loathe that song,” he shared, shocking the late-night host and his audience. “Here’s what it is. I come up to the line and I just don’t want to sing, ‘Life, I love you. All is groovy.’ I don’t want to sing it.” With all due respect to Mr. Simon, we still love hearing it.

13. “Fakin’ It” (1967): Simon and Garfunkel songs

“During some hashish reverie I was thinking to myself, ‘I’m really in a weird position. I earn my living by writing songs and singing songs,’” Paul Simon told Rolling Stone about this tune, in which the duo fess up to battles with self-doubt (“I’ve just been fakin’ it, not really makin’ it”) and the curiosity of celebrity. “It’s only today that this could happen. If I were born 100 years ago I wouldn’t even be in this country. I’d probably be in Vienna or wherever my ancestors came from [and] I would have been a tailor,” he added, explaining that occupation cited in his lyrics.

12. “The Dangling Conversation” (1966)

“It’s intricately worked out. Every word is picked on purpose,” Paul Simon told the New Yorker of the lyrics to this admittedly depressing tune about a couple growing apart. “I’m talking about a relationship where one person recognizes that there’s been a degeneration. He has the epiphany, he sees that we’re not talking about anything. You read your Emily Dickinson and I read Robert Frost, and then they do the New York Times crossword puzzle,” he explained in a 1966 interview about the doomed characters. “They’re not talking anymore but they’re playing a game.”

11. “At the Zoo” (1968): Simon and Garfunkel songs

“Someone told me it’s all happening at the zoo.” Not surprisingly, several zoos — including New York City’s Bronx Zoo and the San Francisco Zoo — would go on to use this earworm for promotional purposes. It was the Central Park Zoo, however, that served as Simon’s inspiration for the quirky lyrics, which finds monkeys standing for honesty and the orangutans skeptical, all while the pigeons “plot in secrecy.”

10. “A Hazy Shade of Winter” (1966)

The Bangles successfully juiced up this tune for the soundtrack of the 1987 film Less Than Zero. “I thought I was a Simon & Garfunkel aficionado but I, somehow, had missed that badass folk-rock song of theirs. I ran to our band rehearsal that night and was like, ‘We have to cover this song,’” lead singer Susanna Hoffs told Vulture about hearing it during the Bangles’ early days. “There’s something about the energy of the song. We did a more rock ’n’ roll version of it,” she added, but the original, of course, is stellar.

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9. “America” (1968): Simon and Garfunkel songs

This, American Songwriter notes, “is essentially a road-trip song, but like all road trips, it tends to reveal as much about the participants as it does about the lands being traversed.” And while it’s inspired by Paul Simon’s travels with his then-girlfriend Kathy Chitty, the song reveals truths about the bond between Simon and his musical partner, too.

The line “And walked off to look for America,” Garfunkel noted in a 1993 interview, “has a real upright, earnest quality because [Paul and I] both have the identical soul at that moment. We come from the identical place in our attitude, and the spine that’s holding us up, we are the same person. Same college kid, striking out.”

8. “The Boxer” (1969)

“I think the song was about me: everybody’s beating me up, and I’m telling you now I’m going to go away if you don’t stop,” Paul Simon revealed in a Playboy interview of the message he was sending in this classic, which features a beautifully simplistic chorus of “lie-la-lie” and a fittingly punching drum element courtesy of famed session musician Hal Blaine.

7. “Scarborough Fair (/Canticle)” (1968): Simon and Garfunkel songs

The duo’s take on this traditional English ballad just missed hitting the Billboard Top 10, peaking at No. 11. Reworked lyrics from an early solo Paul Simon anti-war song, “The Side of a Hill,” are used as the “Canticle” counterpoint woven in to those of the ballad’s. The song, released during the Vietnam war, is one off their Parsley, Sage, Rosemary and Thyme album that “[reflects] the optimism of youth in a time of crisis,” according to the BBC.

6. “Cecilia” (1970)

The drums on this fun track are “all handmade,” Paul Simon told Howard Stern. “There’s no drum in there at all.” After he, Art Garfunkel and others experimented in the studio slapping their knees and other objects, Simon asked for a minute-plus recording of what they did to be looped. “Then I said, ‘Play it and…then I’ll write a song to it. And that’s one of the first songs where I made the track and then wrote the song.”

5. “I Am a Rock” (1966): Simon and Garfunkel songs

Originally from Simon’s 1965 solo album, the duo took their subsequent version of it to No. 3 on the Billboard charts. “There was a year in my life when I didn’t have any friends,” Simon told music journalist Ann Moses about the song’s genesis. “Not because there was nobody that wanted to be my friend, but because I was just living within myself, really. I was all alone all the time.… At the end of the year I said, ‘Well enough. Now I’ve got to go out and grab somebody and hug somebody,’ because you can’t be an island and a rock all your life. [So] everything in the song means the complete opposite. You just can’t be a rock and an island, you just must go out.”

4. “Homeward Bound” (1966)

This song “nailed homesickness with easy grace,” as The Guardian notes of this tune, written when Paul Simon was living in England and missing his then-girlfriend Kathy Chitty as he traveled home from a gig to see her. “It’s like a snapshot, a photograph of a long time ago,” Simon told SongTalk magazine of the sentimental work.

3. “The Sound of Silence” (1965): Simon and Garfunkel songs

“Hello darkness, my old friend.” This No. 1 song, which made it into the Grammy Hall of Fame, is another written by Paul Simon about alienation — and he recalled to Rolling Stone how that topic became sort of a calling card for him as a young songwriter. “Actually, [Bob] Dylan was writing protest, and whatever it was, everybody had a tag. They put a tag on the alienation. And it was a self-fulfilling prophecy, so I wrote alienation songs. Of course we all had a feeling of alienation,” he added, which is perhaps why so many relate to this classic cut.

2. “Mrs. Robinson” (1968)

“It is ‘Mrs. Robinson’ that supplies headlong energy and rising suspense for the last 15 minutes of The Graduate,” Variety notes of this No. 1 hit for Simon and Garfunkel from the 1967 film starring Dustin Hoffman and Anne Bancroft. The lyrics were pretty much a stream of consciousness for Simon, he once told Dick Cavett. “For no particular reason, the words just came into my head,” he said, citing, for example, that Joe DiMaggio entered the picture because “I thought of him as an American hero and that genuine heroes were in short supply.” The singer-songwriter even admitted he was really a Mickey Mantle fan, but DiMaggio had the right amount of syllables for the music! “Mrs. Robinson” went on to win Simon and Garfunkel Grammys for Best Contemporary Pop Performance, Vocal Duo Or Group, and Record of the Year, and it’s been inducted into the Grammy Hall of Fame.

1. “Bridge Over Troubled Water” (1970): Simon and Garfunkel songs

Paul Simon received the prestigious Towering Song Award from the Songwriters Hall of Fame in 2010 for this timeless No. 1 gem “that has influenced our culture in a unique way over many years.” In addition to winning Record of the Year at the Grammys (as well as induction into the the Grammy Hall of Fame), it’s won the admiration of other iconic artists — most notably Aretha Franklin, who brilliantly covered it in 1971 — as well as the hearts of millions of listeners around the world.

"The song’s brilliant,” Art Garfunkel told The Guardian of the tune, given to him to sing by songwriter Simon. “It should be quite possible to do another great version, but it was a hell of a tour de force that I went from so soft to so strong at the end,” he said of preferring his own recording over any remake that followed, apologizing for sounding “inflated… [But] I thought I topped them all.”