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Paul Simon's 10 greatest lyrical compositions

Paul Simon has a wide variety of different songs, and understandably, they’re comprised of different kinds of lines. It is these lyrics that tie his back catalogue together and reflect the quintessence of one of the most honest men in all of music.

In a long and illustrious career that spans over six decades, Simon has touched on every subject under the sun, ranging from the introspective to the comedic. A man whose self-awareness is so vast that it has caused him no end of mental grief over the years, you could say that Paul Simon’s genius is both a blessing and a curse.

Across his career, Simon has shown himself to be capable of some heart-wrenching self-critique, nuanced social commentary and even the odd slight to his bandmate and contemporaries. The most famous chapter in his life in the limelight was undoubtedly as one half of the folk duo Simon & Garfunkel, a brilliant but tempestuous partnership with his school friend and now ex-best friend, Art Garfunkel. Producing some of the most iconic hits of the 1960s, the pair did everything from film soundtracks to providing the counterculture with complex anthems.

The song Paul Simon wrote to parody Bob Dylan

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The pair fused the influences of Woody Guthrie, Lead Belly and The Everly Brothers and made something truly timeless. Like with many great artists, though, fame and its trappings would get in the way, and the two would subsequently be known as music’s resident warring couple. Think Henry II and Eleanor of Aquitane.

After the duo split in 1970, Simon would go on to have an equally celebrated solo career, delivering 1986’s most significant record, the iconic and culturally significant Graceland. It is understandable, then, that to Paul Simon, songwriting is a craft, and one that he takes very seriously.

In George Martin’s 1983 book, Making Music, Simon detailed his songwriting process, and his method is fascinating. “I work with my guitar and a legal pad and use about 50 pages to develop a song,” Simon wrote. “I get going fairly early in the morning, because my mind is sharp, and start by dating the pad and putting down personal comments, such as how I am feeling that day, so that it becomes a diary of sorts.” 

He continued: “Slowly, a song will begin to emerge although sometimes it will stagger along, day after day, making no progress at all. The first page might have all sorts of lines that will never be used, but as I turn the pages, a little thought might come forward and suggest potential for development.”

When one enters the lyrical world of Paul Simon, it is one of oddities and personal tales, humour and great sadness. It is one that not only offers up a great portal in Simon’s mind but also acts as somewhat of a cultural timeline that takes us from the days of counterculture to the hope that the end of the ’80s represented. 

Join us, then, as we dig into Paul Simon’s greatest lyrics.

Paul Simon’s 10 best lyrics:

Countercultural Symbolism – ‘The Sound of Silence’, Wednesday Morning, 3 A.M.

“Silence like a cancer grows.”

Although the original version of this track was a commercial failure, the redubbed effort is a classic. Originally titled ‘The Sounds of Silence’, the song that became ‘The Sound of Silence’ is one of Paul Simon’s highlights from his career. Whilst the basis of the track remains somewhat unclear, there can be no doubt that it is drenched in the spirit and symbolism of the era’s countercultural movement.

Even though Simon has said he penned the record plainly as a youthful “21-year-old”, his paradoxical use of the word “sound” to describe silence was an effective way of commenting on the socio-political apathy of those outside of the countercultural movement.

After the song was released the term “the sound of silence” was used within the counterculture as an alternative to “turning a deaf ear”, which summed up what the movement and youth felt that their respective governments were doing when ignoring their various criticisms.

Emotional Detachment – ‘I Am a Rock’, The Paul Simon Songbook/Sounds of Silence

“I have no need of friendship, friendship causes pains / It’s laughter and it’s loving I disdain / I am a rock I am an island.”

Thematically, ‘I Am a Rock’ is one of Simon’s darkest. It deals with emotional detachment and isolation and it is a song that he does not look back on with great fondness.

The liner notes of the reissue of 1965’s The Paul Simon Songbook read: “This L.P. contains twelve of the songs that I have written over the past two years. There are some here that I would not write today. I don’t believe in them as I once did. I have included them because they played an important role in the transition.

He continued: “It is discomforting, almost painful, to look back over something someone else created and realize that someone else was you. I am not ashamed of where I’ve been and what I’ve thought. It’s just not me anymore. It is perfectly clear to me that the songs I write today will not be mine tomorrow. I don’t regret the loss.

This is definitely the starkest example of just how hard on himself Simon has been over the years.

Pot Shots – ‘A Simple Desultory Philippic’, Parsley, Sage, Rosemary and Thyme

“I been Norman Mailered, Maxwell Taylored / I been John O’Hara’d, McNamara’d / I been Rolling Stoned and Beatled ’til I’m blind / I been Ayn Randed, nearly branded / Communist, ’cause I’m left-handed.”

‘A Simple Desultory Philippic’ is widely regarded as mainly a parody of Bob Dylan’s 1965 classic ‘Subterranean Homesick Blues’. He even directly takes a swipe at Dylan with the line: “So unhip, when you say Dylan he thinks you’re talking about Dylan Thomas”.

Lyrically, he assumes the songwriting guise of Dylan, providing a surreal and humorous list of some of the era’s most famous figures and literary figures too, something the Dylan of the ’60s used as his main weapon of choice.

Showing his penchant for the comedic, Simon directly references not one but four Dylan tunes, the other three being: ‘It’s Alright, Ma (I’m Only Bleeding)’, ‘I Shall Be Free No. 10’ and ‘Rainy Day Women No. 12 & 35’. One of the best records the duo put out, this was a refreshing and psychedelic departure from Simon’s often solemn themes.

Lovesick – ‘Homeward Bound’,  Parsley, Sage, Rosemary and Thyme 

“And each town looks the same to me / The movies and the factories / And every stranger’s face I see / Reminds me that I long to be / Homeward bound / I wish I was.”

Said to have been written in Widnes, Cheshire, of all places, the lovesick ‘Homeward Bound’ was written by Simon when he was missing his girlfriend, Kathy Chitty, of ‘Kathy’s Song’ fame, after a solo show in Liverpool circa 1965. It is also alleged by some fans that he also referenced the same train station in 1969’s ‘The Boxer’. To commemorate the song, there is a plaque on the Liverpool bound platform as Windes train station.

Yearning for his beloved Kathy, the song’s lyrics are drenched in Simon’s longing to be reunited with her. Throughout the song, he discusses emptiness, mediocrity and the desire to be absolved of his current lovesick thoughts. This, added to the isolation he felt whilst travelling amongst the post-industrial landscape of England is brilliant.

Joe DiMaggio’s Heroics – ‘Mrs. Robinson’, Bookends

“Where have you gone, Joe DiMaggio? / Our nation turns its lonely eyes to you / Woo, woo, woo / What’s that you say, Mrs. Robinson? /Jolting Joe has left and gone away.”

The duo’s biggest hit, memorably, made waves as part of the soundtrack for the 1967 Mike Nichols’ classic film The Graduate. It directly referenced baseball hero, Joe DiMaggio, and instead of using his personal baseball hero Mickey Mantle, Simon elected to discuss DiMaggio due to syllables and more importantly, his off-field personality.

Simon would bump into DiMaggio in a New York restaurant in the ’70s, and he was asked: “What I don’t understand, is why you ask where I’ve gone. I just did a Mr. Coffee commercial, I’m a spokesman for the Bowery Savings Bank and I haven’t gone anywhere!”

Simon replied, again containing flecks of his countercultural spirit: “I didn’t mean the lines literally, that I thought of him as an American hero and that genuine heroes were in short supply. He accepted the explanation and thanked me. We shook hands and said good night.”

In a New York Times op-ed in 1999, in the wake of DiMaggio’s death, Simon discussed the meeting and explained that the iconic lines were meant as a candid tribute to DiMaggio’s modest, heroic character, given that we live in an era where popular culture has the power to distort how we perceive our heroes. 

He said: “In these days of Presidential transgressions and apologies and prime-time interviews about private sexual matters, we grieve for Joe DiMaggio and mourn the loss of his grace and dignity, his fierce sense of privacy, his fidelity to the memory of his wife and the power of his silence”.

Lyrical Density And Dylan Again – ‘The Boxer’, Bridge over Troubled Water

“Of every glove that laid him down / And cut him till he cried out / In his anger and his shame / “I am leaving, I am leaving” / But the fighter still remains, he still remains.”

The lyrics touch on a wide range of subjects, and the first section is written in the form of a first-person lament. The narrator discusses his everyday struggle to overcome loneliness and poverty in New York City, showing Simon’s acute awareness of his surroundings.

Many even suggest that some parts of the verses were intended as another attack on Bob Dylan, and that the chorus questions Dylan’s artistic intentions. Then in the final verse, it switches to a third-person outline of a fictional boxer. Simon, however, has said that the lyrics are largely autobiographical, coming from a time when he felt he was being unfairly criticised.

He said: “I think I was reading the Bible around that time. That’s where I think phrases such as ‘workman’s wages’ came from, and ‘seeking out the poorer quarters’. That was biblical. 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.”

Inspiration Can Come From Anywhere – ‘Bridge over Troubled Water’, Bridge over Troubled Water

“Oh, if you need a friend / I’m sailing right behind / Like a bridge over troubled water / I will ease your mind.”

The title track from the duo’s fifth and final album, ‘Bridge over Troubled Water’ is without a doubt their most emotionally stirring. The touching vocals, Garfunkel‘s powerful, almost operatic vocals, it’s a real tearjerker.

Lyrically dense, and hailed as one of the greatest songs ever written, Simon pulled it out of the bag on this one. He claims that he wrote it on a whim in early 1969. The song came so out of the blue he reportedly said to himself: “Where did that come from? It doesn’t seem like me”.

As the song contains an intrinsic gospel character, it comes as little surprise that the title and the central concept was inspired by gospel singer Claude Jeter’s line: “I’ll be your bridge over deep water if you trust in my name,” from his 1958 song ‘Mary Don’t You Weep’. Heart-wrenching both lyrically and musically, have the tissues at the ready.

F*** You Art! (Garfunkel) – ‘The Only Living Boy in New York’, Bridge over Troubled Water

“Tom, get your plane right on time / I know your part’ll go fine / Fly down to Mexico / Doh-n-doh-de-doh-n-doh / And here I am / The only living boy in New York.”

Another classic from the final chapter of the band’s career, is, of course, an emotional entry. As the duo’s relationship had become fractured beyond all repair, it details some of the reasons why their split was inevitable. A thinly veiled message to Garfunkel, in the first verse, the song references an actual incident where Garfunkel eloped to Mexico to film Mike Nichols’ comedy film, Catch-22, something that poor old Simon was jealous and heartbroken by.

Left alone in New York without his songwriting partner, there can be no surprise why Bridge over Troubled Water is drenched in themes of sadness and loneliness. A sombre song, it refers to Garfunkel as ‘Tom’, evoking the duo’s early days when they went by the name of ‘Tom and Jerry’. Unsure of what Garfunkel wanted from his career, Simon says to him: “Let your honesty shine… like it shines on me”. A bit self-indulgent, but we’ll let him off. 

I Can Be Sexy Too… – ‘Cecilia’, Bridge over Troubled Water 

Making love in the afternoon with Cecilia / Up in my bedroom (making love) / I got up to wash my face / When I come back to bed / Someone’s taken my place.”

A direct reference to St. Cecilia, the patron saint of music in the Catholic faith, the song started one night at a party when the duo and friends began banging on a piano bench. Recorded that night on a tape recorder, Simon kept returning to it due to its infectious quality.

The most memorable moment was the lyric, “making love in the afternoon”, which was Simon’s raunchiest at the time. In 2008, Stephen Colbert jokingly asked Simon why the narrator of the song would need to get up and wash his face after making love. To which Simon responded: “Well, it’s the ’60s, so I can’t remember.”


The Midlife Crisis Will Come For All Of Us – ‘You Can Call Me Al’, Graceland

A man walks down the street / He says, “Why am I soft in the middle, now? / Why am I soft in the middle? / The rest of my life is so hard / I need a photo-opportunity / I want a shot at redemption.”

His biggest post-Simon & Garfunkel hit, Simon was well into his 40s when the song was released in 1986. The lyrics are widely discussing a man experiencing a midlife crisis, the lyric: “Where’s my wife and family? What if I die here? Who’ll be my role model?” is the greatest indicator of this. 

Simon has actually explained where the lyrics came from. Appearing on Classic Albums, he said that on the third verse, the lyrics move from the abstract to the more autobiographical. Here, he also describes the real-life journey around apartheid-era South Africa which inspired the album’s themes, and some of the song’s more dream-like imagery.