HomeMusicMusic: 10 Greatest Simon and Garfunkel Songs

Music: 10 Greatest Simon and Garfunkel Songs

Simon & Garfunkel won 10 Grammy Awards and were inducted into the Rock and Roll Hall of Fame in 1990

GRIFFIN: There are few duos more influential and significant in musical history than Paul Simon and Art Garfunkel. The New York duo beautifully paired together complex harmonies, brilliant song writing and vast instrumentation to produce some of the most iconic and beloved songs of all time. A band never afraid to change up their sound to keep things fresh, Simon and Garfunkel had a huge impact on the music industry and surely makes them one of the biggest pop culture icons of the age. Here, April Butterfly and Griffin Kaye will try to rank their greatest songs when limited to just 10. 

Please note this list was comprised of a combined list of both April and Griffin’s opinions. Thus, those ranked highly by both will be higher than those ranked by a singular writer. 


10. The Dangling Conversation

APRIL: A lesser-known gem of the duos catalogue, this song is the one that introduced me to their music.

With passionate harmonies and screaming strings behind them, Paul takes the deep soft lower harmony while Art angelically soars above him, as he often does, but there’s something extra special about these harmonies – it’s enough to illicit a tear. The instrumentation is beautiful with Paul’s always well executed Travis picking and a diversity of backing instruments, from harps to strings and some type of percussive element that picks up tempo with the crescendos of the song.

This song really showcases Paul’s love of writing and literature, which can be seen with his use of imagery. He transports you into the quiet room in the song… “As the sun shines through the curtain lace and shadows wash the room… and we sit and drink our coffee couched in our indifference, like shells upon the shore you can hear the ocean roar.” This can also be seen as he makes references to poems and authors throughout the song such as in the lines, “You read your Emily Dickinson and I my Robert Frost and we note our place with book markers that measure what we’ve lost. Like a poem poorly written we are verses out of rhythm couplets out of rhyme…” And the next line is “in syncopated time” Paul again takes the opportunity to transport you into the song as Art echoes that line in actually syncopated time.

This is really one of my favorite harmonies from Art, after the crescendo “I only kiss your shadow, I cannot feel your hand” Art takes a slightly higher than expected soft harmony on the line “you’re a stranger now unto me” really making you feel the distance in the line. The song is a pleasant excursion into another world, although melancholic, it is peaceful and beautiful.


9. Mrs Robinson

APRIL: A song very prominent in popular culture (albeit less so now), this 1969 hit became the first rock song to win the Grammy Award for Record of the Year, topping the the Billboard Hot 100.

The song was of course used in the movie The Graduate, and the movie gave the song publicity and vice versa. One of the most famous lines is “Where have you gone, Joe DiMaggio? A nation turns its lonely eyes to you”. Paul Simon happened to meet American baseball player DiMaggio at a New York City restaurant in the 1970s and the two discussed that line. The ex-lover of Marilyn Monroe said “What I don’t understand, is why you ask where I’ve gone. I just did a Mr. Coffee commercial… I haven’t gone anywhere!” The line was likely another line of Paul’s that seemed to come out of thin air; he said himself “I don’t know why or where it came from” but he makes sense of it saying he was using DiMaggio to represent heroes of the past.

The hammer on guitar section at the start and throughout the song is extremely memorable and brings a very folk-esque feel to the song in opposition to the satirical feel of the lyrics, the opening “de de de’s” and Paul’s loud, almost talked vocal in some parts. The first Simon and Garfunkel song many people hear and one you have to think of when talking about the duo.


8. Only Living Boy In New York

APRIL: Not as famous a song as ‘The Boxer’ or ‘Mrs. Robinson’ but one that is just as worthy of praise.

It’s a song written by Paul for Art. The duo were originally known as “Tom & Jerry” with Art being Tom. The line “Tom get your plane right on time” alludes to Art’s trip to Mexico to act in a movie adaption of Catch-22. Paul was also supposed to appear in the movie but his part was cut sending him back home to NY without Art, surely feeling as lonely as if he were “the only living boy in New York”.

A shining almost drone like organ plays softly in the back throughout, adding to the atmospheric sound of the song. One of the most notable aspects of the song is the otherworldly harmonies done via use of an echo chamber with 12-15 layered voices creating that harmony.

The song also features maybe one of the most prominent basslines on a Simon & Garfunkel song, played on an 8-string bass by the session musician Joe Osborn. Although the song is about Paul’s loneliness, the lyrics do have an easy-going feel with the line “here I am” ending out the harmonies on the “ahhs”, along with “Hey, I’ve got nothing to do today but smile.” The jangling acoustic, bright bass sound, beaming harmonies and droning organ combine to create a wide and optimistic sound I can’t get enough of, it’s a beautiful song.


7. Scarborough Fair/Canticle

APRIL: This song is a traditional English ballad but is possibly best known by Simon & Garfunkel’s version of it. It documents a singer who asks for tasks of an impossible nature after which “then she’ll be a true love of mine”.

Paul learned the song from English folk singer Martin Carthy, who himself had learned it from the songbook by MacColl and Seeger. Simon and Garfunkel really made it their own, dressing the song with layers of voices simultaneously singing different lines but not in opposition with each other. The lines sung in the back make up the “Canticle” part of the title and they are a reworking of the lyrics in Simon’s 1963 anti-war song, “The Side of a Hill”. That track was written back when Simon took the pseudonym Paul Kane, inspired by the classic 1948 Orson Welles film ‘Citizen Kane’.

They were also set to a new melody, this time mainly composed by Art. With layers of harpsichord, gentle picking acoustic, far off bells, and lilting harmonies the song succeeds in creating a dreamy renaissance atmosphere and is one of my most favourite songs from them. It is a testament to Paul that despite growing up in New York, he managed to create a feel of a medieval folk tune that sounds genuinely Northern English.


6. The Boxer

APRIL: Arguably one of their most famous songs, peaking at number 7 on the Billboard Hot 100 and is 106 on Rolling Stone’s list of the 500 Greatest Songs of All Time.

It opens with an acoustic lick that is neither cheery or melancholy but somewhere in between, as is the mood for the whole song (as I interpret it). The chugging bass harmonica and the all too sing-along-able “lei la lei”s giving levity to the more sorrowful lyrics and the sharp thwack of the heavily reverbed snare. The “lei la lei”s were just place holder lyrics during the creation of the song but remained in the finished product to Paul’s apparent embarrassment. That said, people love to sing along to that part so it all worked out.

The thunderous snare sound is one of my favourite aspects of the song and apparently was created by recording the drum outside an elevator shaft in the Columbia offices. The song has a wide sound, with it all coming to a crescendo at the end of the song before releasing into a peaceful acoustic part similar to the start of the song. Overall, a classic song with themes of loneliness, frustration, and desperation in NYC.


5. Bridge Over Troubled Water

GRIFFIN: Almost unquestionably Simon and Garfunkel’s biggest song, my personal list would likely rank this song higher. 

From the extremely successful 1970 album of the same name, ‘Bridge Over Troubled Water’ was a worldwide hit – topping charts in the US, UK, Canada, France and New Zealand. It stayed atop the US Billboard Hot 100 for 6 weeks and would be the group’s only UK number 1 where it would stay for 3 weeks. It was ranked number 48 on Rolling Stone Magazine’s 500 Greatest Songs Of All Time and is one of the most covered singles of all time. It has been sung by everyone from Elvis Presley to the UK’s National Health Service, being a multi-time UK number 1 singles by a variety of performers. We’ve listened the accomplishments and not even spoken of the song yet! 

Opened by clear, soulful, almost eerie vocals by a solo Art Garfunkel, it is accompanied by a slow and passionate piano. Art’s voice grows more and more as he gradually controls his bellowed vocals. After the perfectly-crafted bridge, the song crescendos with a huge final chorus where a number of more dramatic instruments like more prominent strings and cymbals. Using gospel, soul and pop as inspiration as well as Phil Spector’s “Wall of Sound” technique, both had created one of the longest lasting and most emotional songs of all time. It’s just those vocals – they can’t be matched! 


4. Homeward Bound

GRIFFIN: A favourite song amongst Simon & Garfunkel fans, ‘Homeward Bound’ was the group’s 2nd single after the success of ‘The Sound Of Silence’. A number 2-peaking Canadian, top 5 US Billboard and top 10 UK track – it was written by Paul Simon about returning to his spiritual home in England. 

Soaked in sadness, Simon wrote it on the way from London to Liverpool having recently split from a now-iconic figure in Simon & Garfunkel’s work: Kathy. Kathy Chitty would be a significant love of Simon’s life but the duo would separate when Chitty did not want to move along with Paul to the British Isles.  

It is a slow and nostalgic number about pining to return and being homesick. The saddening is made even more poignant and impactful by the sharp snare drum playing which is prevalent. Its chorus is faster in tempo but keep its message strong as it has a patented vocal harmony between Paul and Art. The lyrics reflect the dullness and repetition of a life Paul has little care for, as illustrated in lines such as: “Every day’s an endless stream/Of cigarettes and magazines” and “Tonight I’ll sing my songs again/I’ll play the game and pretend”. 

A cult favourite, it is a brilliant masterpiece by the group, being a brilliant-made track about returning ‘home’. 


3. Kathy’s Song

GRIFFIN: Paul Simon wrote this sombre love track in 1965 as ode to aforementioned ex-lover Kathy Chitty. Kathy would not only be the focus of this single but many other tracks such as ‘Homeward Bound’ and ‘America’. This song is written in such a way, it would not look out of place in a book of poetry from the likes of Oscar Wilde, John Keats or Elizabeth Barrett Browning. 

The single opens with use of pathetic fallacy to reflect the connection between the characters of the story. This means that the use of weather is used as a way to show the inner emotions and feelings of a person as shown by: “I hear the drizzle of the rain”. Additionally, use of personification is used as the rain is described as “tapping on my roof and walls”. Elsewhere, metaphors (“through the windows of my eyes”, alliteration (“my mind’s distracted and diffused”) and hyperboles (“my thoughts are many miles away”) are used to express the moods of the song writing. 

The 4th verse explains his difficulty in trying to write a song to express his grief and glumness, recounting “I don’t know why I spend my time/Writing songs I can’t believe/With words that tear and strain to rhyme”. The final 2 verses are more traditional romance passages, but nonetheless in keeps with the song and only make it more heart-breaking and tear-inducing. And of course, how can we fail to mention the subtle and soulful guitar playing on the track – the only instrument playing on the song. 


2. The Sound Of Silence

GRIFFIN: It may seem surprising now but this track originally went almost completely unrecognized. Due to this failure, the band broke up as Paul went to England and Art back to studying at Colombia University. It did not become a hit single until remixed with organ and drum overdubs – capitalizing on the electric folk movement popularized by The Byrds and Bob Dylan – in late 1965. It would become a Billboard number 1 which was only discovered by the duo when Simon picked up a printed paper listing the Billboard chart listings. 

Some of the best-known opening lyrics of all-time, it opens “Hello darkness, my old friend”. A 3-minute yet loaded song, it could very well be their best-written track as their debuting single was about the increasing alienation in the mid ‘60s. Almost fully with dual vocal harmonies, it features some of their best combined voices as both fluctuate in singing scales. A simple guitar and voice song, it would be the song that would go on to kickstart the careers of both musicians. 


1. America

GRIFFIN: Inspired by a 5-day long hitchhike across the US by Simon and girlfriend Kathy, ‘America’ was one of the last tracks recorded for the ‘Bookends’ album. The song – described by Art Garfunkel himself as about “young lovers with their adventure and optimism” – reflects its inspiration talking about people searching for the nation in a metaphor and literal sense. 

The track starts with some of the most well-known and poignant opening lines from the duo, as they croon: “Let us be lovers, we’ll marry our fortunes together/I’ve got some real estate here in my bag”. It uses some of the patented traits of Simon and Garfunkel such as massively crescendoing towards the end and mentions of themes such as Kathy and cigarettes and magazines. The narrator lovingly lists the actively he has taken up whilst touring with their lover across the USA such as Pittsburgh, Saginaw and New Jersey. “Pioneer Of FM Rock” Pete Foretale has interpreted it as a “metaphor to remind us all of the lost souls wandering the highways and byways of mid-sixties America, struggling to navigate the rapids of despair and hope, optimism and disillusionment”. After a long and solemn build, it eventually climaxes with bold symbol crashes. 

In a year seeing social changes such as Robert Kennedy and Martin Luther King’s assassinations, escalation in Vietnam and the USSR, and the Black Power Olympics movement, it was truly a patriotic nod to their homeland. It was initially released as a B-side in 1972 to promote the Greatest Hits album of Paul and Art but would become the A-side soon after. 

A unique single that describes the trip of a still young and unknowing duo crossing unchartered territory to find the light of America, it is easily one of the best songs ever written as well as Griffin and April’s top song by music’s greatest twosome known as Simon and Garfunkel. 


Simon and Garfunkel were an American folk-rock duo with many a catchy hit, have we missed anything from this list? let us know on twitter

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