10 Best Simon & Garfunkel Songs

Paul Simon and Art Garfunkel met in 1953, when they appeared in their school’s production of Alice in Wonderland – Simon played the White Rabbit and Garfunkel the Cheshire Cat. Learning to harmonise together, they released their first single, ‘Hey Schoolgirl’ in 1957 as Tom & Jerry. Initially inspired by the Everly Brothers, their first album was the trad folk of 1964’s Wednesday Morning 3 A.M.. With scarily sincere versions of songs like ‘Go Tell It On The Mountain’ it wasn’t successful, and Simon decamped to London.

When an electrified version of the first album’s ‘The Sounds of Silence’ became a #1 hit, Simon hurried back to the US and the duo enjoyed half a decade of mega-success before going their separate ways after 1970’s Bridge Over Troubled Water.

In the header, I used the cover image from the 1981 compilation The Simon and Garfunkel Collection. Interestingly, Simon and Garfunkel don’t appear on the cover – they weren’t on speaking terms so their roles are taken by two actors. Despite only having five albums of material to choose from, there was no space for the top ten hits ‘Cecilia’, ‘I Am A Rock’, ‘Mrs. Robinson’, or the 1975 reunion single ‘My Little Town’.

10 Best Simon and Garfunkel Songs

#10: Homeward Bound

from Parsley, Sage, Rosemary, and Thyme, 1966
Simon composed ‘Homeward Bound’ in the UK, while Simon and Garfunkel were on hiatus after their debut album, writing it on a railway platform. A plaque on Widnes railway station commemorates the song. Like ‘Kathy’s Song’ and ‘America’, ‘Homeward Bound’ was written about Simon’s UK-based girlfriend Kathy Chitty.


#9: The Sound of Silence

from Sounds of Silence, 1966
Simon and Garfunkel’s first record, Wednesday Morning, 3 A.M., was a trad-folk effort that largely sank without a trace. But the Paul Simon song ‘The Sounds of Silence’ began to receive radio airplay, leading producer Tom Johnston to overdub electric guitars and a rhythm section. Because Simon and Garfunkel had split, they weren’t notified of the new version, but it became a number one hit, leading to the duo’s hasty reformation. Retitled ‘The Sound of Silence’ in its re-released form, the song tackles alienation.


#8: A Hazy Shade of Winter

from Bookends, 1968
‘A Hazy Shade of Winter’ is just about Simon & Garfunkel’s hardest rocking track, with its fast pace and driving guitar riff. It’s another song written by Simon during his time in the UK, and it reflects frustration with failed artistic ambition. The Bangles’ 1987 cover from the movie Less Than Zero is also worthwhile.


#7: Punky’s Dilemma

Simon and Garfunkel Bookends

from Bookends, 1968
This track from Bookends is almost the only non-single on this list. Like ’59th Street Bridge Song’, ‘Punky’s Dilemma’ has a child-like quality. The lyrics are cryptic although they indicate a desire for simplicity – the song opens with the lines “wish I was a Kellogg’s Cornflake/Floatin’ in my bowl, takin’ movies/Relaxin’ awhile”. Surprisingly for such a personal and idiosyncratic song, Barbra Streisand recorded a cover in 1969.


#6: Scarborough Fair/Canticle

from Parsley, Sage, Rosemary, and Thyme, 1966
Simon spent time in London while Simon and Garfunkel were on hiatus, and learned ‘Scarborough Fair’ from Martin Carthy. Simon and Garfunkel’s version interpolates the English folk song with Simon’s anti-war song ‘The Side of a Hill’, and Garfunkel received his only ever writing credit for his contribution to the duo’s rearrangement. The ornate baroque-pop production of 1966 is the perfect foil for the pair’s pristine vocals.


#5: The 59th Street Bridge Song (Feelin’ Groovy)

from Parsley, Sage, Rosemary, and Thyme, 1966
Like some of Cat Stevens’ work, ‘The 59th Street Bridge Song’ has a charming, nursery-rhyme quality. It’s also closer to jazz than anything else in the Simon & Garfunkel catalogue – Dave Brubeck’s rhythm section of Joe Morello and Eugene Wright guest. Reportedly Simon now hates ‘Feeling Groovy’ – during the pair’s 1993 shows, comedian Steve Martin came on stage and mimed getting stoned during the song.


#4: Bridge Over Troubled Water

from Bridge Over Troubled Water, 1970
Art Garfunkel takes the spotlight for this gospel ballad, with beautiful piano from Larry Knechtel. While Garfunkel’s tenor takes the lead, the song’s most magical moment is when Simon’s harmony joins on the third verse (“sail on silver girl”). Simon’s songwriting has contributed several phrases to the English lexicon – “bridge over troubled water” is one of them.


#3: America

from Bookends, 1968
‘America’ was inspired by a road trip that Simon took across America with Kathy Chitty in 1964. While ‘America’ starts as a personal story, it takes on a much wider meaning capturing a sense of isolation in a quickly changing world – “I’m empty and aching and I don’t know why”. Garfunkel’s angelic harmonies help to build the song to its thrilling climax. It’s in 3/4, also known as waltz time.


#2: The Boxer

from Bridge Over Troubled Water, 1970
Simon and Garfunkel’s only release of 1969 was the single ‘The Boxer’. It’s one of Simon’s best songs but it’s also distinguished by its production- in particular, Hal Blaine’s thunderous snare drum in the chorus, recorded from the bottom of an elevator shaft. It’s an autobiographical tale from Simon, reflecting his frustration at criticism of his work. The “lie-la-lie” chorus was originally intended as a placeholder but stuck. On 3 June 2016, Simon interrupted his performance of ‘The Boxer’ to inform the audience that Muhammad Ali had just passed away.


#1: The Only Living Boy In New York

from Bridge Over Troubled Water, 1970
The creation of 1970’s Grammy-winning Bridge Over Troubled Water was disrupted by Art Garfunkel filming Catch-22 in Mexico. ‘The Only Living Boy In New York’ is a thinly veiled reference to the situation, with Simon referring to Garfunkel as “Tom”, his stage name from the days they performed as Tom & Jerry. It was never a single, but it’s still taken on a life of its own – its gorgeous tunes and layered harmonies exemplify the majestic sound of the Bridge album. It provided the name of a 2017 film, and has been covered (most notably by Everything But The Girl) and appeared in soundtracks frequently.

Did I miss your favourite Simon and Garfunkel song?

Read More

32 Comments

  1. Bridge Over Troubled Water
    My Little Town
    Scarborough Fair
    Mrs. Robinson
    At the Zoo
    The Boxer
    Homeward Bound
    I Am a Rock
    Sounds of Silence
    Hazy Shade of Winter

      • I just realized that all the ones on my list are all their hits, except for At The Zoo I think. I really don’t know if that was a hit single or not. I know all the other ones were for sure.
        I didn’t used to like Punky’s by Barbra Streisand until I learned to like the Simon & Garfunkel one, but I can kind of appreciate it now. She did it almost like one of those art things they used to have back then.

  2. Great list. I’ve known many of these tunes since I was like 8 or 9 years old from their (second) 1972 Greatest Hits compilation, which my older sister had on vinyl – one of the best greatest hits compilations, IMHO. I still love these songs. I also dig Paul Simon’s acoustic guitar playing.

    • I was trying to figure out what Paul Simon played on Simon and Garfunkel records, since other guitarists are credited too, like Glen Campbell. It’s just him on ‘Peace Like A River’ from his first solo album, which has some nice guitar.

      • Great tune I did not know. Man, even during my best times playing acoustic guitar (when I would practice every day, oftentimes for more than one hour), I couldn’t have played stuff like that. Practicing is important but it only got me to a certain point.

        • Paul’s a good player. And hell, that was like 50 years ago. He takes his playing seriously. It really drives a lot of his stuff. He was definitely a big part of the folk scene with Bert Jansch and those guys. In fact, “Anji” is a cover of Jansch’s cover of a tune called “Angie.”

          • I read a book called Fire and Rain, which follows The Beatles, Simon and Garfunkel, James Taylor, and CSNY through the year 1970. There’s a story about a session guitarist being able to play a lick that Simon couldn’t, and Simon working really hard to nail it.

          • Not easy to keep up with studio musicians. There’s a good backstory to ‘The Boxer’ guitar intro in Wikipedia that’s worth a read.

      • I think I read somewhere that playing Anji was a kind of test to see if you were up to the mark as a folk guitarist in that era.

        Lots of very good guitarists emerged from 1960s folk – Richard Thompson, John Martyn, Roger McGuinn, Joni Mitchell, Jansch and Redbourn, Nick Drake, James Taylor,….

  3. Graham, we are on the same page…I would only switch 3 and 1 and you would pretty much have mine… although I would have to add I am a Rock somewhere in the top 10. That would be my only change… but with what you have you cannot go wrong. I love the inclusion of Punky’s Dilemma.

    • Yup, I think you’ve commented that you like America before. I was reading that it wasn’t actually a single until 1972, with the Greatest Hits. Barbra Streisand’s ‘Punky’s Dilemma’ is interesting…

  4. I think you’ve got all my favourites here, though I would likely place Boxer at number one with America a close second (it was that scene in Almost Famous that did it for me).

  5. Great list!
    For Emily is a good one too.
    This guys were really big. Clearly at the beginning Paul Simon was following Dylan. But he adapted fast taking the path of The Byrds and of course The Beatles. The singing skills from Art Garfunkel were fantastic for his new direction. Some of their songs are timeless pieces. Just listen to your list.

    • Yup, I don’t think it’s quite as strong as Simon’s ten best solo songs but it’s very good, especially given it almost all happened in a small window (1966-1970).

    • The Boxer’s awesome. I forgot to mention it on my post, but in the live 1981 version there’s an extra verse instead of the piccolo trumpet solo:

      Now the years are rolling by me—
      They are rockin’ evenly.
      I am older than I once was,
      And younger than I’ll be.
      That’s not unusual;
      No, it isn’t strange:
      After changes upon changes
      We are more or less the same;
      After changes we are more or less the same.

  6. Difficult task- narrowing down a Top 10 for S&G… I do know The Boxer would be my #1- you had it close to the top! Great list- and not all are the usual suspect big hits.

  7. I did this without looking at your choices (or anyone’s) thus far:

    10. I Am a Rock
    9. Homeward Bound
    8. The Dangling Conversation
    7. Scarborough Fair/Canticle
    6. Overs
    5. America
    4. Mrs. Robinson
    3. Sounds of Silence
    2. Bridge Over Troubled Water
    1. The Boxer

Leave a Reply to 2loud2oldmusic Cancel reply

%d bloggers like this: