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The 10 Best Paul Simon Songs of All-Time

Paul Simon

In 1962, Jerry Landis reached No.97 on the Billboard Hot 100 with a song called The Long Teen Ranger. It was a forgettable song and Jerry Landis was a forgettable artist. It was only when he reverted back to his birth name of Paul Simon and teamed up with his childhood buddy Art Garfunkel that he stopped being forgettable and started being legendary like a true rock music star. His work as one-half of Simon and Garfunkel would be enough to earn him a place among the greatest singer-songwriters of all time, but his solo projects have proved no less extraordinary. These are the 10 best Paul Simon songs of all time.

10. Darling Lorraine

After spending the previous 15 years challenging himself and his listeners with ever more experimental sounds, Simon decided to sit back and relax on 2000’s You’re The One. Not that that makes it a bad album – it may lack ambition, but it’s as elegant and well-crafted an album as you’d expect from Simon. The jury at the Grammy’s clearly agreed, making Simon the first-ever artist to be nominated for Album of the Year in five consecutive decades. Its highlight is Darling Lorraine, a poignant exploration of a relationship that follows its ups, downs, fights, and reconciliations. Like most of Simon’s work, there are moments of playfulness, but when he reveals Darling Lorraine’s death at the end, the humor turns to heartbreak.

9. Duncan

Duncan, the third single from Simon’s self-titled 1972 album, didn’t get much love when it was first released. In the years since, it’s become one of his most treasured songs, and one of the few ‘non-hits’ that still gets trotted out at concerts. In a way that’s reminiscent of Simon and Garfunkel’s The Boxer, it tells the story of a homesick young boy as he navigates the loneliness and challenges of life far from home. It may not have made an impression on the charts, but it’s still a lovely thing.

8. Peace Like A River

By the time Paul Simon released his second solo album in 1972 (his first release after the break up of Simon and Garfunkel), we already suspected he was something a bit special. But could he deliver the goods without his old buddy Art? He could. Peace Like a River doesn’t just show off his talents as a songwriter, it highlights his thorough understanding of the entire musical experience. A song is more than the sum of its words, something Simon has always understood on an instinctive level. With a soaring chorus and gritty guitar setting the tone for Simon’s narrative, the song is a plump, juicy delight.

7. 50 Ways to Leave Your Lover

If there’s ever an opportunity to inject some humor into a song, Simon takes it. 50 Ways to Leave Your Lover might not have the most wholesome of subject matters, but Simons’s deft wordplay (which he apparently based on a rhyming song he was teaching his young son) is too playful for anyone to take offense. The song sauntered all the way to No.1 and remains of Simon’s most popular songs to this day.

6. Diamonds on the Soles of Her Shoes

Obviously, recording an album in apartheid-era South Africa didn’t earn Simon a lot of Brownie points. But leaving aside the controversy, there’s no denying that Graceland was a revolution. Which it needed to be. His solo albums had been selling poorly for several years, and his reunion with Garfunkel had fizzled out almost before it started. If Simon was to be saved from obscurity, he needed a hit. He got one. When he performed Diamonds on the Soles of Her Shoes alongside Ladysmith Black Mambazo on Saturday Night Live in May 1986, it shook up the nation. Nothing like it had been heard before, not from Simon and not from anyone else either. It wasn’t the best song on the album, but it was our first bite of a very juicy apple. For that reason if nothing else, it deserves a place on our list of the 10 best Paul Simon songs of all time.

5. Still Crazy After All These Years

The title track of Simon’s fourth studio album didn’t perform as well as the album’s other singles, but it still managed to scrape a pass into the Top 40. Said to describe an encounter with his ex-wife, Peggy Harper, the bittersweet lyrics are perfectly complemented by a jazzy arrangement of sax, strings, and piano. Simon’s slightly plaintive vocals add to the nostalgic, reflective vibe.

4. You Can Call Me Al

The success of You Can Call Me Al wasn’t entirely down to that goofy video with Chevy Chase. It didn’t hurt things though. Neither did the fact that MTV decided to play it on almost constant rotation. Said by Wikipedia to have been inspired by a meeting with French composer Pierre Boulez in which Boulez spent the whole thing referring to Paul as Al and his then wide Peggy as Betty, the song has sometimes been interpreted as being about a man going through a midlife crisis. According to Simon, it’s more an autobiographical account of the experiences he had in South Africa while recording Graceland. Either way, it gave Simon one of his biggest ever hits.

3. Kodachrome

As Rolling Stone says, Paul Simon has written a lot of great first lines to his songs, but nothing compares to “When I think back on all the crap I learned in high school it’s a wonder I can think at all” from 1973’s “Kodachrome.” The rest of the song is just as blissful, its rich seam of nostalgia shot through with bitterness. Released as the first single to There Goes Rhymin’ Simon, it took Simon to No. 2 in the charts.

2. American Tune

American Tune showcase’s Simon’s strengths as a songwriter. He rarely touches on political themes, but here, he comes close. Written shortly after Nixon was elected, it touches on feelings of national pride and patriotism without giving way to sentimentality or jingoism. Since peaking at No. 38 on the Billboard Hot 100, it’s become one of his most popular and covered tracks, with everyone from Willie Nelson to Elvis Costello recording their own interpretations.

1. Graceland

By the mid-1980s, Simon’s career had taken a downward turn. His solo output had become shaky and his reunion with Art Garfunkel had shuddered to a halt in the midst of escalating tensions. He was on the brink of becoming a relic. And then he took a trip to South Africa, met up with Ladysmith Black Mambazo, and gave his career a massive shot in the arm with Graceland. Sure, a lot of critics took umbrage with him for violating the cultural boycott against South Africa, but that didn’t diminish just how revolutionary and culturally significant the album was. Even now, over 30 years after its release, it’s still widely regarded as one of the best albums of all time. Its titular track is effervescent. Brimming with hope and wit, it ranks as one of Simon’s simplest but most beautiful solo achievements.

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