Paul Simon became a master of many genres throughout his career (Image: Getty)
Few artists have navigated different sides of pop music with as much ability and elegance as Paul Simon.
First rising to fame in the 1960s as one-half of Simon & Garfunkel – arguably the defining duo of American folk rock – Simon began a solo career in 1972 that would cement his legacy as one of music’s most poetic and unpredictable voices.
From his early projects in reggae and Andean instrumentation to the culture-shifting leap into South African music with Graceland, Simon’s solo catalogue is littered with moments of quiet revelation and rhythmic revolution.
In 2016, Rolling Stone asked its readers to vote for the greatest songs from Simon’s solo career. Here, we list the ranking of his hits and deep cuts:
10. Duncan
The humble third single from Simon’s self-titled debut solo album didn’t crack the Top 50, but it’s aged more gracefully than many chart-toppers from the same era.
The song tells the story of Lincoln Duncan, a young man who leaves his home in Nova Scotia and goes through the American northeast. It’s a narrative ballad full of poetry in its themes of travel, struggle and self-discovery.
A tender flute solo, courtesy of Los Incas’ Jorge Milchberg, gives the track its wistful charm, and today, Simon often includes it in his setlists.
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9. Hearts and Bones
‘Hearts and Bones’ was written during Simon’s turbulent relationship with Star Wars star Carrie Fisher – they married briefly in 1983 before divorcing a year later.
The lyrics are full of emotional detail, chronicling a road trip taken by the couple (“one and one-half wandering Jews”) and the quiet paiin of a love slipping away. It’s introspective and raw, a rarity even in Simon’s emotionally rich discography.
Originally intended for a Simon & Garfunkel reunion album, Simon ultimately decided to keep the song – and the entire album, for that matter – for himself. Although not a commercial success, the track has become a critical favorite.
8. The Obvious Child
After the global triumph of Graceland, Simon swapped South Africa for Brazil – and made The Rhythm of the Saints steeped in Afro-Brazilian rhythms and spiritual reflection.
Its lead track, ‘The Obvious Child’, pulses with percussion from Olodum, a legendary Salvador-based drumming group whose sound Simon discovered while exploring Brazilian street music. Lyrically, it’s about aging, memory and acceptance, delivered with Simon’s usual lyrical sleight of hand.
While it peaked only at No. 92 in the U.S., the song earned a cult following. It opened Simon’s massive 1991 Central Park concert and even inspired the title of Jenny Slate’s acclaimed 2014 indie film.
7. 50 Ways to Leave Your Lover
Written in the wake of his divorce from Peggy Harper, Simon wrote about heartbreak and pasted it on a groovy sound.
The song’s verses explore emotional confusion, while the chorus offers comic relief in the form of cartoonish breakup advice. It was boosted by Steve Gadd’s now-iconic drum intro and has lyrics inspired from playing rhyming games with his young son, Harper.
It became Simon’s most commercially successful single – hitting the top of Billboard’s Hot 100 charts.
6. Late in the Evening
A well-known gem, ‘Late in the Evening’ came from the soundtrack of One-Trick Pony, the 1980 film Paul Simon wrote and starred in – but did not reach much commercial success.
The song is autobiographical, tracking Simon’s early love for music and his formative years of late-night gigs and smoky rooms. It’s funky, driven by Latin-influenced horns and percussion, and became a Top 10 hit in 1980.
5. Diamonds on the Soles of Her Shoes
By 1986, Simon’s last few records hadn’t been loved by audiences, and Simon & Garfunkel had been through a failed reunion. So he went to Johannesburg and made Graceland.
‘Diamonds on the Soles of Her Shoes’ debuted on Saturday Night Live, featuring Simon and South African vocal group Ladysmith Black Mambazo. The harmonies stood out among other tracks on American radio, and the song’s story of a rich girl who “makes the sign of a teaspoon” proved to be moving.
While not a major chart hit, it became a cultural icon, both celebrated and criticized for its complicated political context.
4. Still Crazy After All These Years
The title track from Simon’s Grammy-winning 1975 album is both melancholic and mature. Against a gentle melody, the lyrics tell the story of a man staring middle age in the face and wondering what it all means.
Simon’s performance of the song on Saturday Night Live – while wearing a turkey costume, no less – became a legendary moment in the show’s early history. He even reprised it at the show’s 40th anniversary.
3. You Can Call Me Al
‘You Can Call Me Al’ is effortlessly joyful and has a strange origin story. The title came from a party where French composer Pierre Boulez accidentally called Simon “Al” and his then-wife Peggy “Betty.” The inside joke turned into a surreal set of lyrics about identity, existential angst and spiritual searching – to a bouncy pop beat.
The track features a famous penny whistle solo, a bass run played backward, and a video with Chevy Chase that became a MTV and VH1 favourite.
It only reached No. 23 in the U.S. on its initial release but became a much bigger hit globally – and a concert essential ever since.
2. Graceland
Originally a placeholder title intended to be swapped out, ‘Graceland’ was written in the shadow of Simon’s split from Carrie Fisher – a journey through emotional wreckage in search of healing.
The title track of his most celebrated album, it’s a blend of American rock, South African mbaqanga and confessional songwriting. It’s also full of pop, poetry and political awareness.
Whether he actually took his son Harper on the trip or not, as the lyrics suggest, is still debated since 1986.
1. Kodachrome
“When I think back on all the crap I learned in high school, it’s a wonder I can think at all” is how ‘Kodachrome’ starts, and it sets the tone for the entire track.
Released as the lead single from There Goes Rhymin’ Simon, it hit No. 2 on the U.S. charts and solidified Simon’s solo superstardom. The song, named after a brand of colour film, is a bittersweet look at memory and how photographs – like songs – can both preserve and distort the past.
Simon retired it from his live shows after 2012, but fans have nonetheless crowned it his best song of all time.