5 Nearly Perfect Paul Simon Songs That Should Be Required Listening For Younger Generations

It takes a true talent like Paul Simon to score a Valentine's Day No. 1 hit with an ironic tune called "50 Ways to Leave Your Lover." Simon's skillful, expressive lyrics and experimental musical modes made him a unicorn among the other singer-songwriters of his generation. His evolution from folk troubadour to pop music's resident smart guy to collector of global sounds and world music innovator is a study in creative curiosity and musical ingenuity. But Simon's greater works tend to get shuffled to the back of the jukebox, so it's high time some of his near-perfect tunes resurface for young music lovers to discover.

Pretty much everyone knows songs like "Bridge Over Troubled Water" or the much-covered 1964 classic "The Sound of Silence" are some of his finest works as a songwriter and beloved standards in pop music; there's no sense in revisiting them. We think there are equal treasures in Simon's deeper track list that demand appreciation by listeners and budding songwriters of the 21^st century. Songs like "Hearts and Bones" that describe the strange numbness of a love falling apart, and "Spirit Voices," which examines the mysterious powers of the natural world, demonstrate the depth and range of Simon's abilities as a musical magician. Our five picks for the best Simon songs will introduce younger listeners to big ideas and small wonders, all delivered with canny wonder, artistry, and catchy melodies you can't shake off.

Of all the '60s folk musicians who transitioned into the world of commercial pop, Paul Simon is one of the few who captured the angst of real life without losing his philosophical delivery. In "Slip Slidin' Away," he muses about the blandness of life being mistaken for a peak experience. Verses describe characters who've followed unique paths toward love, only to regret the end results. All the while, deceptively simple doo-wop harmonies float by beneath it all, making it easier for listeners to focus on the meaning without getting lost in the instrumentation.

Ultimately, Simon reminds us, it's all out of our hands: "God only knows," he explains, taking a more universal top-down view, "God makes his plans / The information's unavailable to the mortal man. We work at our jobs, collect our pay / Believe we're gliding down the highway when in fact we're slip slidin' away." It's a sharp, timeless description of contemporary lostness; the song may be more than four decades old, but it's just as relevant to today's humans as it was when it was released in 1977.

Just as importantly, "Slip Slidin' Away" is an earworm, with a chorus that digs in and sticks around. That's the genius of Simon's songwriting, whether they're his own recordings or songs he's written for other performers: Songs like this can be enjoyed by younger listeners on multiple levels, depending on where your head and your heart happen to be when you listen.

The complex bond of Paul Simon's well-documented romance with and marriage to Hollywood legend Carrie Fisher are captured in the lovely 1983 track "Hearts and Bones," a song that projects the course of a relationship from midway point to finish. Though the two eventually divorced in real life, the song was composed and recorded while their relationship was still ongoing — a projection of how Simon could see their love story playing out.

Paul Simon is maybe a little too honest in his description of how things could go here, singing, "And tell me why, why won't you love me for who I am where I am? / He said, 'Cause that's not the way the world is, baby / This is how I love you, baby.'" So rather than being a traditional love song, "Hearts and Bones" turns out to be a study of how two people can lose themselves and their idealism when trying to make things work. "You take two bodies and you twirl them into one," Simon describes, "Their hearts and their bones, and they won't come undone." Call it an open-eyed love song minus the romance.

Their up-and-down relationship lasted 12 years, resulting in more than just one telling tune. But "Hearts and Bones" has a maturity and elegance that deserves to be resurrected and appreciated by new audiences, and even studied by young songwriters for its deft portrayal of a real-life love affair.

Paul Simon's foray into world music broke big in 1986 with "Graceland," a milestone album that paired him with noted South African musicians Ladysmith Black Mambazo. "Under African Skies" is a chiming tribute to how the earliest influences of music have a lasting impact throughout the lives of those who hear the calling. "This is the story of how we begin to remember," Simon sings, harmonizing with fellow '70s icon to help with harmony vocals, the legendary Linda Ronstadt, who became a part of the song's lyrics as well.

"Under African Skies" references the childhood of Ladysmith's founder, Joseph Shabalala, and his childhood in South Africa. Simon prompted Ronstadt for her first memory as a child and turned it into a verse saluting her own summoning into the music world: "I said take this child, Lord / From Tucson, Arizona / Give her the wings to fly through harmony /And she won't bother you no more." 

Young music listeners searching for rich analog artistry in a digital world will appreciate the nimble guitar work paired with crystalline harmonies, sharing a message of how music is a life-changing force. As Simon explains, "These are the roots of rhythm / And the roots of rhythm remain."

Paul Simon's world music exploration took a sharp left turn from the sunny, sky-bright tones of South Africa to the richly shaded sounds of South America with his stunning 1990 album, "The Rhythm of the Saints." More lushly spiritual and yearning than the splashy, upbeat songs on "Graceland," these works are meditations on the mysteries of life as seen through the eyes of a curious wanderer. Among them is a stand-out called "Spirit Voices" that summarizes this unending search for greater meaning. It's Simon's trademark songwriting mode, only this time he takes it into the shadows and brings back an inner light that feels far more significant than almost anything else in his repertoire.

Simon sees through the eyes of a newcomer to this strange and mystical region as he visits a folk healer and reports back: "Some stories are magical, meant to be sung / Songs from the mouth of the river when the world was young / And all of these spirit voices rule the night." Then later, he calls to the greater forces, "Sing rain water, sea water, river water, holy water / Wrap this child in mercy, heal her" and drinks a concoction that lets him commune with the jungle. It's a bedtime story, a lullaby, and a hymn to the riddles of the natural world, set to a soothing tribal beat. With "Spirit Voices," Simon conjures up musical medicine, a healing sound work that reminds contemporary listeners the world is much more magical than what the algorithms show us.

Rather than sticking with his poetic leanings, Paul Simon took a more literary approach with "Darling Lorraine" from his 2000 album "You're the One." The recounting of a man's devotion to a woman from his first glance to her final breath, the song unrolls like a short story. "She's so hot, she's so cool / I'm not, I'm just a fool / In love with darling Lorraine," says the main character, Frank, something of a loser who lucked out when Lorraine decided to marry him. The ups and downs of a long-term marriage and the falling out of love that sometimes accompanies it ensue, with both Frank and Lorraine growing sick of one another.

But their lives take a dark turn when Lorraine becomes ill; suddenly, Frank is devoted and attentive, realizing what their life together has meant. "All the trees were washed with April rain / And the moon in the meadow took darling Lorraine," Simon sings plaintively, with haunting Afro-Cuban rhythms propelling the narrative all the way through. Minor-key chords shift into major-key territory when the mood lightens, giving each section a personality that matches the tone of the lyrics.

This is a complex work that should be studied in a college course dissecting Simon's work for its artistic value. It also happens to be a heart-wrenching cinematic tune for young listeners who love depth in their music.