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The Best Paul Simon Songs You’ve Never Heard

In honor of his new album, a quick look into Simon’s back catalog

At 74, Paul Simon has written several lives’ worth of indelible songs — and, depending on when you were born, one of those lifetimes was likely the soundtrack to your formative years. In the 1960s, he and his partner Art Garfunkel scored the anxiety and optimism of the baby boomers; his solo career began in the early ‘70s, and took on that decade’s growing disillusionment. By 1986’s Graceland, he had remade himself yet again, teaming up with South African musicians to produce some of the most timeless, accessible work of his career. Since then, he’s written a Broadway musical, been nominated for an Oscar, toured with Bob Dylan and continued to record album after album.

In honor of his latest release, Stranger to Stranger, let’s take a quick look into Simon’s back catalog. Avoiding songs released as singles, here are 10 deep tracks that speak to his seemingly inexhaustible ability to wring insights from everyday occurrences, over music that melds pop and folk and occasionally flirts with funk, R&B and salsa. There are plenty of Paul Simon hits we all know — here are 10 non-hits that also deserve to be heard.

“Congratulations” (1972)

The final track off Paul Simon’s underrated 1972 album sums up the LP’s melodic, melancholy worldview: Love is fleeting, nobody can find happiness, people let you down, and adulthood is an endless series of bitter compromises. (Perhaps not surprisingly, the singer-songwriter was about to turn the big 3–0 when he recorded Paul Simon.) But despite the ironic title, “Congratulations” is a lovely keyboard-and-guitar ballad that transforms past heartbreaks into beautifully resigned, weary music. “Won’t you answer me, please,” Simon asks, “Can a man and a woman/Live together in peace?” Much of the rest of his career has been spent trying to resolve that question.

“I’d Do It for Your Love” (1975)

This lightly jazzy tune from Simon’s first Album of the Year Grammy-winner features a narrator recalling a romantic relationship always felled by bad luck. It rained on their wedding day, they both got sick, the gift he bought her got ruined on the way home — and yet, he’s still willing to hope for the best. Along the way, Simon shows off his gift for marrying the everyday and the poetic: “The sting of reason/The splash of tears/The Northern and the Southern Hemispheres/Love emerges and it disappears.”

“The Late Great Johnny Ace” (1983)

1983’s Hearts and Bones was deemed a commercial disappointment, inspiring Simon to shift direction radically and embrace the South African sounds that informed Graceland. But this album-closer is among his finest and most evocative tracks. “The Late Great Johnny Ace” spans three time periods — 1954, 1964 and 1980 — to connect the accidental self-inflicted gunshot death of R&B singer Johnny Ace to President John Kennedy’s assassination to the murder of John Lennon, all tied together by Philip Glass’s virtuosic instrumental coda. Adding to the song’s legend, Simon played it live at the 1981 Central Park concert where he and Art Garfunkel reunited, and where his solo performance was interrupted by a crazed man who rushed the stage. It was a deeply unsettling moment, especially for a song partly about shocking violence.

“I Know What I Know” (1986)

Simon’s second Album of the Year winner drew from mbaqanga, a South African style of music that features jumpy rhythms and danceable guitar. (“It sounded like very early rock ‘n’ roll to me — black, urban, mid-‘50s rock ‘n’ roll,” he told Rolling Stone at the time of Graceland’s release.) “I Know What I Know” was inspired by the music of General M.D. Shirring and the Gaza Sisters, who played on Simon’s refurbished track, adding the chanted vocals, percolating percussion and funky riffs. And although the songwriter’s tales of love gone wrong usually veer toward the morose, here he’s in a feisty mood, verbally sparring with a potential mate who can’t figure out where she’s met him before. Best line in a song filled with winners: “She said, ‘There’s something about you/that really reminds me of money.’/She was the kind of girl/who could say things that/weren’t that funny.”

“Crazy Love, Vol. II” (1986)

This Graceland charmer found second life thanks to the 2011 romantic drama Like Crazy, which starred Anton Yelchin and Felicity Jones as a temperamental couple. In the characters’ puppy-love phase, they listen to “Crazy Love, Vol. II,” which is a hint that things probably aren’t going to work out for these two. You see, the song is told from the perspective of a man going through a brutal divorce — “Well, this will eat up a year of my life/And then there’s all that weight to be lost” — and despite Ray Phiri’s gorgeous guitar lines, there’s nothing romantic or hopeful about the picture it paints.

“Can’t Run But” (1990)

For the follow-up to Graceland, Simon moved, metaphorically, from South Africa to South America, falling under the sway of Brazilian rhythms. Melding talking drum, castanets, and other percussive devices, “Can’t Run But” rides a moody Latin groove to portray a world undone by nuclear radiation, romantic discord and the infiltration of commerce into art. That’s a wide-ranging list of grievances, but the singer makes it work; his musicians craft a sonic landscape that’s dizzying and hypnotic, suggesting a society in which we’re all running out of control.

“Can I Forgive Him” (1998)

After the career-revitalizing triumphs of Graceland and The Rhythm of the Saints, Simon wrote a musical about Salvador Agron, a Puerto Rican gang member who killed two teens in 1959 in New York when he was only 16. The Capeman was critically savaged and a commercial failure, and the accompanying album got dismissive reviews. But this acoustic-guitar ballad, sung as a conversation between Agron’s mother and one of his victim’s mothers, is a stark, compassionate investigation of anguish and anger. At a time when capital punishment and immigration rights are still widely debated, “Can I Forgive Him” finds the humanity beneath the talking points.

“That’s Where I Belong” (2000)

Simon made his name writing songs about love’s impermanence, but around the time of 2000’s You’re the One, he seemed to turn a corner personally, focusing on tunes about domestic life and being grateful for the time he’s got left. (Perhaps not coincidentally, he married musician Edie Brickell, his third wife, in 1992, and it’s been his longest-running relationship.) The album’s opening cut sets the tone for this reflective collection of songs: In “That’s Where I Belong,” he salutes the power of a good melody and a happy love life. “When I see you smiling/When I hear you singing/Lavender and roses/Every ending a beginning,” he declares, and the track’s gentle mixture of guitars, drums and keyboards make it all sound like a dream come true.

“How Can You Live in the Northeast?” (2006)

“There are albums that I do that are sort of like adventure albums,” Simon said in 2011. “I will go off into some area that I don’t really know a lot about and try to write there.” 2006’s Surprise fits this category: Hooking up with U2 and Talking Heads producer Brian Eno, Simon focused more on electronic sounds and ethereal soundscapes. The dreamy, stirring “How Can You Live in the Northeast?” impressionistically captures the mood of post-9/11 America, obliquely referencing everything from Hurricane Katrina to the country’s growing xenophobia. Appropriately, he’s not offering solutions but, instead, trying to make sense of a world in which religion, ethnicity and age serve as ways to divide people.

“Rewrite” (2011)

Simon has often written in the voice of fictional characters, but “Rewrite” features one of his most poignant narrators. A Vietnam vet working at a car wash who’s lost his family for unspecified reasons tells us about his circumstances and how he hopes that he isn’t too old to turn his life around. Over beautiful guitars and subtle percussion, our hero talks about his existence as if it’s a book he’s writing, trying to get the ending right. Pushing 70, Simon demonstrated he still had a dramatist’s eye for the telling small detail — and a songwriter’s gift for melodies that get jammed into your skull.

Tim Grierson is one-half of The New Republic’s film column Grierson and Leitch. He is also a frequent contributor to Rolling Stone and Vulture as well as the author of six books, including a biography of Public Enemy.