Credit: Far Out / Bernard Gotfryd
October 27th, 2026 · 4:49pm GMT
It’s with a wry wink and a smile that Paul Simon sings, “I don’t know why I spend my time / writing songs I can’t believe / with words that tear and strain to rhyme”. He’s written hundreds of songs over the years, and I’m not sure if any of them have fallen foul of the accusations he accosts himself with in ‘Kathy’.
In stark contrast, as a songwriter, the only ironic criticism that naysayers could justly yield against him is perfection. Words fold into melodies so gracefully in his songs that you can’t wrestle one from the other as you read them on paper. And the words in question always feel lived-in and earnest, brilliantly capturing the witty New York vernacular with his own unique brand of listlessness.
His back catalogue is also something that he has always remained acutely aware of. “The language starts to get more interesting in Hearts and Bones. The imagery started to get a little interesting,” Simon said of his own work, highlighting his 1983 album as a turning point perceptible to nobody but himself.
In a similar act of self-discerning, when he recently appeared on The Late Show with Stephen Colbert, he picked out his seven best songs. ‘America’, ‘Kathy’, ‘Hearts and Bones’ and ‘The Obvious Child’ are all notable absentees for my money, but it‘s evident from his own picks that he’s a man who knows what it is that makes something a hit.
As Bob Dylan said, “I consider him one of the preeminent songwriters of our time. Every song he does has got a vitality you don’t find everywhere.”
Conor Oberst similarly said, “I grew up with my folks listening to him. But as I got into songwriting, I realized how profound what he does actually is. His work over the years is a treasure trove of ideas.”
And even the great Paul McCartney once proclaimed, “I think Paul Simon has written some amazing songs. I wouldn’t want to just say one of them but he’s certainly written some great stuff.”
The seven tracks that Simon champions are all largely classics, but which of them stand out as his defining masterpieces? Well, ranking them is certainly no easy task, especially given his evolving style where each chapter has its own merits, but we’ll give it a whirl…
Ranking Paul Simon’s seven favourite songs: ADD AS A PREFERRED SOURCE ON GOOGLE 