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Paul Simon’s Early Years: 10 Fascinating Pre–Simon and Garfunkel Songs

Explore hits and misses from legendary singer-songwriter’s formative days

Revisit Paul Simon's earliest efforts as a singer-songwriter with our round-up of obscure late-Fifties and early-Sixties tracks.

Revisit Paul Simon's earliest efforts as a singer-songwriter with our round-up of obscure late-Fifties and early-Sixties tracks.

James Kriegsmann/Michael Ochs Archives/Getty

Paul Simon – the critically acclaimed hitmaker, the sophisticated composer, the folk-rock poet who gave voice to the hopes and anxieties of a generation – seemed to enter the world stage fully formed with the release of Simon and Garfunkel’s debut single, “The Sound of Silence,” in the fall of 1965. And that was OK with him. Few knew of his secret past as a one-time teenage pop star in the late Fifties alongside his schoolmate Art Garfunkel, when the two were known as Tom and Jerry. For years after, he toiled in relative obscurity, releasing a string of derivative but catchy songs under a whole Rolodex of impractical stage names.

Simon eventually started recording music under his own name, and when stardom followed, he became increasingly embarrassed by these early songs, viewing them as the audio equivalent of compromising baby photos that could surface at any moment and torpedo his new reputation as a mature songwriter. He even went to court in 1967 to successfully block their release.

Though the sensation is understandable, the songs are nothing to be ashamed of. Some may be corny, but the best show flashes of Simon’s future brilliance. His feelings toward these primitive efforts appear to have softened over the years, and he even performed several in recent concerts as an affectionate tribute to his past.

In honor of Simon’s 75th birthday, we take a look at 10 early musical efforts that provide a fascinating insight into his creative development.

Paul Simon, Fascinating, Pre–Simon and Garfunkel, Songs

Tom and Jerry, “Hey Schoolgirl” (1957)

Long before there was Simon and Garfunkel, there was just Paul and Artie – two high school seniors bonded by a passion for rock & roll. One afternoon while trying to recall lyrics to the Everly Brothers' "Hey Doll Baby," the 15-year-olds accidentally stumbled onto words that would give them an early taste of their future fame. Written in under an hour, "Hey Schoolgirl" became their party piece, performed at amateur stages across their home borough of Queens, New York. The relentlessly upbeat number kicks off with a slew of nonsense syllables in the mold of Little Richard's "Tutti Frutti" ("A-wop-bom-a-loo-mop-a-lomp-bom-bom!") before settling into harmonies that would do the Everlys proud.

Convinced of the song's potential, the boys ventured into Manhattan to pitch "Hey Schoolgirl" to the Tin Pan Alley publishers centered in the heart of midtown. Together they banged on doors throughout the famous Brill Building, desperate to perform their tune for anyone who would listen. Unfortunately, no one would. So they decided to record a demo that they could hand out to executives, thus eliminating the need for awkward in-person recitals.

In early October of 1957, they ponied up $25 and crammed into the photo-booth-sized live room at Sanders Record Studios on Seventh Avenue and West 48th Street. In a move straight out of Hollywood fantasy, a promoter named Sid Prosen happened to overhear the session and offered to sign the pair on the spot. Contracts were drawn up, their parents consulted, and in days they were officially artists on Prosen's Big Records label.

It was feared that their given names were "too ethnic-sounding" to play in Middle America, so the boys commenced the time honored showbiz tradition of picking flashy pseudonyms. "Tom and Jerry" served as a starting point – borrowed from the cartoon series – which they had already used for local gigs. Garfunkel settled on "Tom Graph," a reference to both his love of mathematics and habit of marking the chart position of favorite pop songs on graph paper. Simon christened himself "Jerry Landis," after the surname of then-girlfriend Sue Landis.

"Hey Schoolgirl" hit shelves less than a month later in early November, backed by another original, "Dancin' Wild." Prosen, no stranger to less-than-legal tactics, reportedly slipped DJ Alan Freed $200 to play the song on his influential radio program, where it quickly gained traction. Soon it entered regular rotation on AM playlists across the country. Variety gave the tune its "Best Bet" seal of approval, and Cash Box made it their "Sleeper of the Week."

Prosen also managed to get Tom and Jerry a spot on Dick Clark's seminal afternoon music program, American Bandstand. The teenagers were stunned to learn that they would share a bill with Jerry Lee Lewis, who performed his latest single, "Great Balls of Fire," just before their set. "It's was an incredible thing to have happen to you in your adolescence," Simon recalled. "I had picked up the guitar because I wanted to be like Elvis Presley, and suddenly there I was!"

The song went on to sell over 100,000 copies, enough to bring it to a respectable Number 49 on the Billboard charts. More importantly to the high schoolers, it earned them major respect from their peers. "You can't imagine what it was like having a hit record at 16," he said later. "It made me a neighborhood hero."

Paul Simon, Fascinating, Pre–Simon and Garfunkel, Songs

True Taylor, “True or False” (1958)

Garfunkel was rarely comfortable being one half of Tom and Jerry. "It was all over my head," he says in Marc Eliot's Paul Simon: A Life. "I never would have done it if Paul hadn't pulled me along. I was too fearful of the competitive, adult world of rock & roll." After earning $2,000 in royalties of from "Hey Schoolgirl," he put it in the bank and resumed the studies that he hoped would lead him to Columbia University.

Meanwhile, the adult world of rock & roll seemed to suit Simon just fine. He spent his own share of the royalties on a fire-red Chevy Impala convertible, further cementing his status as a neighborhood hero. Though he enjoyed being part of a group, he had the ambition to go it alone if need be. When Tom and Jerry were signing their deal with Prosen, Simon also quietly inked a solo contract. With Garfunkel temporarily sidelined at school, it seemed like the perfect opportunity to test his own musical strength.

He collaborated with his father, Lee Simon, a professional bassist and dance bandleader, who had composed a song called "True or False." The lyrics consist of a list of questions put to a potential love interest: "Do you like to call me on the telephone?" "Are you excited to make a date?" "Are you sad when I go away?" Though it sounds like what it is – a rock song written by someone's dad – the younger Simon was enthusiastic enough to go along with it.

"True or False" packs some spiky guitar fills, but its lyrics are often rendered unintelligible due to Simon's hiccupy hee-haw, equally indebted to Buddy Holly and Elvis Presley. Credited to "True Taylor," a pseudonym dreamed up by Prosen, the song would be Paul Simon's very first solo release. Issued in early 1958 on the Big Records imprint, it failed to make a dent in the charts.

But it did put a dent in his friendship with Garfunkel, who viewed the venture as a serious betrayal. Though it's unclear whether Simon deliberately kept his (occasionally errant) bandmate in the dark, the incident damaged relations between the old friends and their families. While it would ultimately blow over in the short term, it would become a sore spot for years to come. More than its musical legacy, "True or False" is notable for sewing the seeds of resentment that would shape the pair's relationship for the rest of their lives.

Paul Simon, Fascinating, Pre–Simon and Garfunkel, Songs

Tom and Jerry, “Our Song” (1958)

After the True Taylor incident, Simon and Garfunkel put their differences aside and continued their Tom and Jerry partnership. They were determined to capitalize on the success of "Hey Schoolgirl," and their follow-up was on shelves by the following February. "Our Song," a deceptively cheery rockabilly breakup number recorded the same day as "Hey Schoolgirl," failed to match the impact of its predecessor. They tried again with "That's My Story" and "Baby Talk" released over the following year, but to no avail.

Simon's prized Impala served as a particularly dramatic symbol of Tom and Jerry's fall from grace. While he was cruising through Queens one night, a freak electrical accident caused the car to overheat. Smoke billowed from under the hood and the terrified teen barely managed to escape the vehicle before it burst into flames – just outside the Garfunkels' house, no less. When the fire department extinguished the blaze, all that remained of Simon's "Hey Schoolgirl" royalties was a charred heap of metal.

They would release several more songs – including "I'm Lonesome" (1959), "I'll Drown in My Tears" (1961), and "Surrender, Please, Surrender" (1962) – but their Tom & Jerry incarnation was as wrecked as the Impala.

Paul Simon, Fascinating, Pre–Simon and Garfunkel, Songs

Jerry Landis, “Anna Belle” (1960)

As Tom and Jerry petered out, Simon began to focus on production work. Though still in college, he developed a lucrative side business cutting demos for hire. For $25 dollars a session, he would flesh out a songwriter's lead sheet by singing and recording a wide range of instruments. Future hits from Dion, Fabian and Bobbie Vee were all given the treatment. "That's where I learned how to stack vocals and to do overdubs – how to make records," he later told Life magazine.

Around this time he met fellow Queens College student Carole Klein (later King), and together they established an unofficial duo. "Carole would play piano and drums and sing. I would sing and play guitar and bass," Simon recalled. "The game was to make a demo at demo prices and then sell it to a record company. Maybe you'd wind up investing $300 for musicians and studio time, but if you did something really good, you could get as much as $1,000 for it. I was never interested in being in groups, I was only after that $700 profit."

King's career would take off when "Will You Still Love Me Tomorrow," a song written with her young husband Gerry Goffin, became a Number One hit for the Shirelles in December 1960. While Simon was happy for his friend, it was hard for him not to feel a twinge of jealousy. The twinge turned into an all-out ache when Goffin and King's music publisher turned him down.

But his experience recording demos in a variety of styles made him a remarkably versatile performer, and he started recording a series of songs under his Jerry Landis moniker. Though he later dismissed this output as "fodder for eunuchs," a number of them hold up surprisingly well. His first post–True Taylor solo release was the rollicking "Anna Belle," a familiar amalgam of Buddy Holly and the Everly Brothers. Billboard predicted its sales potential as "moderate" in its "New Records" column, but even this tepid account was overly optimistic. The song sold about 100 copies across the country.

Paul Simon, Fascinating, Pre–Simon and Garfunkel, Songs

The Mystics, “Let Me Steal Your Heart Away” (1961)

The Mystics had a hit in 1959 with the Doc Pomus–Mort Shuman penned "Husbaye," and a year later they were still struggling to find a successful follow-up. When lead singer Phil Cracolici resigned, their manager Jim Gribble eyed young Simon, who had been lurking around his door at 1697 Broadway.

"On any given day there would be dozens of guys and girls hanging out in his office, waiting for him to listen to them and decide if he wanted to put them on a record," bass vocalist Al Contrera recalled to Marc Eliot. "Among the crowd that always seemed to be there was this one kid, Jerry Landis [sic] … with his guitar, off in a corner somewhere, always practicing and writing down songs. He was always there, kind of small and unnoticeable, among these crowds of eager teens waiting and wanting to be discovered."

After auditioning "a million guys," they decided to give the diminutive kid a shot. "We liked the way he sounded, so we agreed to do the new songs we had with him singing lead." He was an odd match for the band of sharp-tongued kids from Bensonhurst, Brooklyn. "We had all been kid runners for the mob … so we were from the streets, we were tough guys, and we didn't take shit from nobody. And here was Jerry, this little nerdy guy from Queens with a guitar as big as he was, leading us."

They recorded three tracks, none of which Simon wrote: "All Through the Night," "I Begin to Think Again of You," and "Let Me Steal Your Heart Away." Simon's vocals are mixed into oblivion on the first two titles, but he can be clearly heard on the latter. None made any impact on the public, and soon Simon and the Mystics decided to part ways. "It was really a mutual decision," Contrera said. "We were too tough for him, and we didn't think we would all look good together onstage. … But by the time we let him go, I remember him saying something about he wanted to do his own thing anyway, and singing with a group was not it." Going forward, his attention would be on Jerry Landis.

Paul Simon, Fascinating, Pre–Simon and Garfunkel, Songs

Jerry Landis, “Play Me a Sad Song” (1961)

If you were to judge solely from his songwriting output, it would appear that Paul Simon was down in the dumps for a significant part of his younger years. A scan of his early song titles reads like a not-so-subtle cry for solace and emotional succor: “I Wish I Weren’t In Love,” “I’m Lonely,” “Loneliness.” Chief among these lover’s laments is “Play Me a Sad Song.” A lyrical sibling to Ricky Nelson’s “Lonesome Town” – and recorded with the same hauntingly sparse instrumental backing – the narrator urges “Mr. DJ” to put on something down-tempo so he can continue his wallowing unabated.

But appearances can be deceiving. By all accounts, the maudlin Jerry Landis bore little resemblance to the true-life Simon. Listening closer to these tunes, these heartbreak clichés ring false, as if Simon is going through the motions. It’s bad acting put to standard-issue late-Fifties sock-hop balladry. Still, the songs offer a portrait of a budding songwriter chasing trends until he can find his own voice.

Paul Simon, Fascinating, Pre–Simon and Garfunkel, Songs

Tico and the Triumphs, “Motorcycle” (1961)

Having failed to replicate the past glories of his "Hey Schoolgirl" days, Simon decided to try his luck as a pop Svengali. After trawling local dances and talent competitions, the 19-year-old came across a vocal quartet from Parsons Junior High (his alma mater) with formidable harmonies. He approached the group after a performance and, after dropping numerous references to his Tom and Jerry fame, offered to manage them. The kids were suitably impressed by his local pop star status and quickly agreed.

Simon soon took over all creative aspects of the band's career, including songwriting and record production. Dubbing them Tico (his favorite record label) and the Triumphs (a hip sports car), he presided over extensive practice sessions held in his parent's basement. Originally intending to stay behind the scenes, Simon ended his self-imposed vocal exile when one of the members resigned. He took the lead on "Motorcycle," a surprisingly hard-rocking number introduced by a blast of exhaust from his own car.

Released in October 1961, "Motorcycle" attracted attention in several major cities. It even earned a coveted spot on the playlist of WINS-AM, featuring future "Fifth Beatle" Murray the K. Ironically, the song's initial success would prove its undoing. The low-budget label, unable to meet production demands, was forced into bankruptcy. By the time Simon sold the masters to the larger Amy Records, the moment had passed. He could take comfort in knowing that he cracked the Billboard Hot 100, scraping in at Number 99.

Paul Simon, Fascinating, Pre–Simon and Garfunkel, Songs

Tico and the Triumphs, “Wild Flower” (1962)

In a painfully transparent attempt to mimic the near-success of “Motorcycle,” Simon set his sights on a different vehicle for Tico and the Triumphs’ next single, “Express Train.” The record failed to enter the charts, but the interesting B side seems to prophesize his future interest in world music.

“Wild Flower” has its roots in the Tokens’ then-current hit “The Lion Sleeps Tonight (Mimoweh),” an adaptation of a Zulu folk song popularized by Pete Seeger and the Weavers. Inspired to create an exotic tune of his own, Simon reached for an ambitious collection of sounds. Culturally, the finished product is a mess: acoustic guitars, a vaguely Arabian sax solo and bogus Hawaiian chants strung together from random syllables, all over a Bo Diddley rhythm. But the musical vision is admirable.

Paul Simon, Fascinating, Pre–Simon and Garfunkel, Songs

Jerry Landis, “The Lone Teen Ranger” (1962)

Even future voices of a generation have to start somewhere. Simon penned this galloping tribute to the television Western The Lone Ranger, with the result falling somewhere between novelty schmaltz and a genuine attempt at a pop song. It was a strange choice considering that the series had ceased production five years earlier, but the show provided the unique lyrical premise of a teenage boy whose romantic overtures are constantly foiled by his love’s obsession with the titular TV cowboy. “She even kissed the TV set/Oh, it’s a cryin’ shame,” sings the man later responsible for finely wrought classics like “Bridge Over Troubled Water” and “I Am a Rock.”

While undoubtedly goofy, the song is not without charm. It kicks off with more sound effects – this time pistol shots – a doo-wop-y cowboy yodel and a hearty “Hi-yo, Silver – away,” famous as the Lone Ranger’s battle cry. Several other catch phrases are weaved in (“Who was that masked man?”), and the song’s sax solo cleverly references the show’s theme tune, “The William Tell Overture.”

Though Billboard, Cash Box and other trade papers pegged it as a hit, “The Lone Teen Ranger” would rise to no higher than Number 97 on the charts.

Paul Simon, Fascinating, Pre–Simon and Garfunkel, Songs

Paul Kane, “Carlos Dominguez” (1964)

By 1963, Simon was languishing in the backrooms of the music industry, working as a song plugger for the publishing company Edward B. Marks. For $150 a week, he was tasked with shilling the staff songwriters' latest batch of demos to producers and record executives looking for the next smash. Unable (or unwilling) to market anyone's songs but his own, Simon loathed the job.

Still, he was able to parlay the role into a publishing deal for himself, signing over four of his recent songs: "He Was My Brother," "Bleecker Street," "The Side of a Hill" and "Carlos Dominguez." The latter is a Spanish-tinged ballad that chronicles an "unhappy man" who travels the Earth looking for a universal enlightenment – and ultimately finds none. "I search for a truth, all I found was a lie," he sings. "I look for eternity, but I find all men die. I'm looking for answers, but I find only fate. I'm searching for love, all I find in this world is hate."

The following spring, when Simon was living in the United Kingdom, he was surprised to learn that a small London publishing company had licensed the song, giving it to the hugely popular easy-listening crooner Val Doonican. Eager to show thanks, Simon dropped by the West End offices and encountered co-owner, Les Lowe. "This young American sat there in our tiny, cramped office, took off his duffle coat and took out his guitar and started to play strange songs," Lowe told Marc Eliot. "I was very impressed and had no doubt that Paul's work was unique."

The impromptu session earned Simon a British publishing deal and a record contract. He opted to record "He Was My Brother" – a protest song eventually dedicated to the memory of Andrew Goodman, the murdered civil-rights worker and Simon's Queens College classmate – with "Carlos Dominguez" as the B side. It was released in the U.K. early that May under the name Paul Kane, a pseudonym that reflected Simon's love of Citizen Kane.

Though the words clearly spring from the mind of a confused college student, deeply troubled by the state of the world he has inherited from the older generation, the skillful flamenco guitar points to Simon's early infatuation with music from other cultures. This tendency would eventually blossom on Simon and Garfunkel tracks like "El Condor Pasa" and his solo masterpiece, Graceland. What's more, these same feelings of alienation and disenchantment would be revisited on the song that launched his career, "The Sound of Silence"

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