This Day in Rock History (Buddy Holly Sets New Direction in Last Recording Session)

Oct. 21, 1958—Buddy Holly wrapped up his most recent recording session with songs that pointed to a new musical direction, yielding two more hits, including “It Doesn’t Matter Anymore,” covered by countless musicians. Little did he or his growing fan base imagine that the 22-year-old rock ‘n’ roller from Lubbock, Texas, had finished his last studio work. A little over three months later, this enormously influential singer-songwriter would die in a plane crash alongside fellow idols Ritchie Valens and the Big Bopper.

I have touched briefly on the influence of Holly before, in a blog post on John Fogarty’s speech inducting him posthumously into the Rock ‘n’ Roll Hall of Fame. But the circumstances surrounding his last time in a studio represent one of the great might-have-beens in entertainment history.

Speed propelled his guitar sound and his often impulsive decisions in the last months of his life—so much so, friends said later, that they wondered if he had a premonition that his life would be truncated. Only six hours after meeting Maria Elena Santiago, a receptionist at his music publisher’s, he proposed marriage to her. 

Determined on larger horizons beyond Lubbock, he had relocated to Greenwich Village in New York, the home city of his bride. Although love provided the impetus for the decision, the relocation also put him closer to a metropolis with a whole mélange of musical styles beyond rockabilly that increasingly fascinated him. 

The move was paralleled by a major shift in his business and creative life: suspicions that his earnings were being diverted led to a split with manager Norman Petty, and the breakup precipitated an additional parting of the ways with backup band The Crickets. Facing an immediate cash-flow problem to cope with starting a new family and pending litigation with Petty, he reached out to form an alliance with a singer-songwriter he had once viewed as a potential rival: 17-year-old teen pop sensation Paul Anka. 

For a time in 1957, Holly had been annoyed that Anka’s “Diana” had prevented his own work from topping the charts. But he’d gotten friendly with the youngster while touring Australia early in 1958, and by autumn, as Holly charted a new course for his life, he even discussed forming a music company with him, according to Anka’s memoir, My Way. 

Anka let it be known that he had a song that Holly might use when he was done with it. By mid-October, Holly was so anxious to see it that Anka just managed to finish it the day of the session. Taking out his guitar, he quickly learned its structure before passing it along to Brunswick-Coral A&R head Dick Jacobs. "He told me it was a new song that Paul Anka had just written specially for him, called 'It Doesn't Matter Anymore,' and it had to be in the session," Jacobs recalled afterward.

It was Jacobs who had the responsibility for helping Holly work toward a new sound at Coral Studios, at the Pythian Temple at West 70^th Street. The year before, Holly had told a Canadian deejay, “I’d prefer singing…something a little more quieter.” “Less raucous” might have been a more apt description, because, for the four songs Holly wanted to perform, Jacobs was creating arrangements for an 18-piece studio orchestra, filled with strings, harp and tenor saxophone.

“I had no time to harmonize the violins or write intricate parts, so I wrote them all pizzicato,” Jacobs said later about “It Doesn't Matter Anymore.” “That was the most unplanned thing I have ever written in my life.”

Whatever astonishment Jacobs may have felt about Holly’s sudden request for a song that the singer had, uncharacteristically, not written himself, it was swallowed up by the needs of the moment and his great respect for Holly (whom he later termed the least temperamental singer he’d ever worked with). The musicians in the orchestra started out rather more skeptical, but by the time Holly was done with his vocal, they, too, had become converts, breaking into smiles and even applause.

The string-laden arrangements should not obscure the daring nature of Holly’s interpretation of the Anka tune. First, it can be regarded as a pioneering example of the post-breakup “kiss-off” song, best exemplified by The Beatles’ “Norwegian Wood,” Fleetwood Mac’s “Go Your Own Way,” Bon Jovi’s “You Give Love a Bad Name,” and Bob Dylan’s “Like a Rolling Stone."

Second, his rapid evolution so soon in his career would show other rock ‘n’ rollers to follow the imperative to absorb new influences. Six years before George Martin employed strings on Paul McCartney’s plaintive ballad “Yesterday,” Holly had gotten there first. Beach Boy Brian Wilson's experimentation with French horns and other classical instruments on Pet Sounds was likewise made infinitely easier to promote to record company execs because of the success Holly had enjoyed in this last session.

Remarkably, though, this was the first time Holly had used strings so extensively in his work, and he was bursting with even more ideas. 

Maria Elena remarked years later that her husband had talked about also opening a London studio, and biographer Philip Norman has noted that Holly wanted to absorb jazz and classical music into his songs, and he was willing to range far afield: working with Ray Charles and Mahalia Jackson, and an album of South American songs that he would sing in Spanish. He was already showing a willingness to experiment, to push beyond limits—a propensity that would have prevented him from becoming confined in a creative straitjacket.

“It Doesn’t Matter Anymore” became Holly’s last Top 20 single (and the first to reach #1 in the UK after an artist's death). But it was only one of four songs from that last session that each had their favorites. Holly himself told his brother Larry that “Raining in My Heart” would be regarded as “the best record I’ve ever put out.” “Moondreams” and “True Love Ways” also have their partisans.

Early on, Elvis Presley had opened Holly’s eyes to the possibilities of rock ‘n’ roll. But it is no disrespect to The King to suggest that Holly represented an even greater influence on the next crucial wave of rock ‘n’ rollers. 

Two groups at the forefront of the British Invasion even took on names that paid tribute to the budding legend: The Beatles (a play on The Crickets) and, more explicitly, The Hollies. But that hardly exhausts the list. Think also of the Rolling Stones, the Kinks, Bob Dylan, Bruce Springsteen, Jimmy Page, Elton John, Eric Clapton, and Elvis Costello (whose nerdy early look mirrored the black horn-rimmed glasses that became Holly’s trademark).

 

Writing in Britain’s Independent on the 50^th anniversary of what Don McLean famously termed, in “American Pie,” “The Day the Music Died,” Spencer Leigh catalogued his influence succinctly: “Buddy Holly created a series of firsts, although most of them need qualification – the first singer/songwriter of the rock 'n' roll era; the first to have the lead/rhythm/bass/drums line-up; the first to use studio trickery such as double-tracking; the first to have strings on a rock 'n 'roll record; the first to use the Fender Stratocaster; and the first rock 'n' roll star to wear glasses.”

“He managed to forge a sound that was just unique, but it sounded simple enough for everyone to say, ‘I can have a go at that,’” recalls Keith Richards in an interview for a PBS documentary, Rave On: A Buddy Holly Biography. “You would get close, but it would be something to aim for. And I think for the body of musicians of my age at that time, that it was like a magnet.”