A Leisurely Look @ Buddy Holly

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On February 3, 1959, rock ‘n’ roll suffered its first major tragedy. A plane carrying three hit-making performers crashed in winter storm conditions in Clear Lake, Iowa. Aboard were Texas DJ and recent recording star J.P. “The Big Bopper” Richardson, who’s song “Chantilly Lace” had been one of the biggest hits of 1958. Also lost that day was 17-year-old Ritchie Valens who had enjoyed a handful of hit songs and showed promise as a guitarist and composer. The third performer to lose his life that day was Buddy Holly who had made considerable contributions to rock ‘n’ roll during his all-too-brief career.

Charles Hardin Holley was born September 7, 1936 in Lubbock, Texas. “Buddy”, as he was nicknamed early in life, had 3 older siblings and a trace of Native American blood. His family attended the Baptist church in Lubbock. His older brother, Larry, served in the Pacific during World War 2 and brought home a guitar and brother Travis taught Buddy to play it.


Growing up in Texas, Buddy was naturally enamoured of country and western music and after graduating from Lubbock High School in 1955, he put a band together. That year, Buddy met and opened for Elvis Presley in Lubbock. Watching Presley perform inspired Buddy to turn towards a sound that was closer to rock ‘n’ roll. In the fall, a Nashville scout saw Holley perform and he was signed to Decca Records in February of ’56. On this initial contract Buddy’s last name was misspelled “Holly” and he was known thereafter as “Buddy Holly”.

It was the usual “machine” at Decca and Holly was unhappy with the lack of creative control he had there. This desire to govern his own sound is one of the earliest manifestations of the many things that made Holly an innovative force in music. He had admired the work of producer and promoter Norman Petty in New Mexico and sought him out. Buddy took with him his new group comprised of bassist Joe B. Mauldin, drummer Jerry Allison and rhythm guitarist Niki Sullivan and the demo of their original song “That’ll Be the Day”. Petty loved the sound – especially that of Holly’s ringing lead guitar – and sent the song off to Brunswick Records who loved it as well and planned to release it. The group hired Norman Petty to be their manager.

buddy2Here’s where things get a little murky when it comes to Holly’s recordings, the name they were released under and on what label. Still under contract to Decca, Holly could not have a record released on Brunswick under the name “Buddy Holly” so the 45s Brunswick put out by the group bore the name “The Crickets” (Allison’s idea). In a sly record company move, Brunswick agreed to give Holly the artistic control he sought over his recordings but they also left much of the financial responsibilities to him, as well.  Petty and Holly soon learned that Brunswick was a subsidiary of Decca so recording under the name “Buddy Holly” for Brunswick was OK. In the end, “The Crickets” were released on Brunswick and “Buddy Holly” would record for yet another subsidiary, Coral. Holly held contracts with both labels.

“That’ll Be the Day” – inspired by an oft-repeated phrase in John Wayne’s The Searchers – was a big hit for Holly and Co. It reached #1 on the pop charts, #2 on the R&B charts and was #1 in the UK. It was a hit for Linda Ronstadt in 1976 but perhaps the most notable cover was by the Quarrymen – it was the first song recorded by the group that would become the Beatles.

The group’s next single was also a hit and also became an iconic recording from this era. “Peggy Sue” b/w “Everyday” rocketed up the charts and was credited to Buddy Holly who began to become the focus, the group sometimes being credited as “Buddy Holly and the Crickets”. The group’s first album, The ‘Chirping’ Crickets, was released in November of ’57 and contained several other hit songs including “Oh, Boy!”, “Not Fade Away” (his coolest song?), “Maybe Baby” and a lesser-known but stellar ballad with a fine vocal from Holly, “It’s Too Late”, written by Chuck Willis.


The new year of 1958 saw Holly place more hits on the charts with “Rave On” (his finest record?), “It’s So Easy” and “Heartbeat”. He also began to distance himself from the Crickets and record with R&B and jazz bands. During a visit to a music publishing company, he met María Elena Santiago from San Juan, Puerto Rico, who was employed there. He asked her out on a date on that first meeting and on that first date – five hours in – proposed marriage. The wedding took place in August of ’58 with Petty advising Holly to keep the marriage a secret so as not to upset Buddy’s female fans. This irked Holly and increased the tension that had begun to exist between client and manager. For some time, Holly and the Crickets had been concerned about Petty’s handling of the money they were making.


Holly was nothing if not forward-thinking. He had ambitions to pursue many different types of music and various aspects of the music business. With his wife he frequented New York’s jazz clubs and Holly expressed to María his desire to learn piano and flamenco guitar. He was planning collaborations with soul singer Ray Charles and gospel singer Mahalia Jackson and he enrolled in Lee Strasberg’s Actors Studio. He also moved into record production, producing the debut single from Lubbock DJ Waylon Jennings. The close of 1958 saw him truly stepping out on his own. He recorded songs with acoustic guitar including “Crying, Waiting, Hoping” and was also backed by an orchestra for “It Doesn’t Matter Anymore” (written by Canadian Paul Anka and perhaps Holly’s finest vocal performance), “Raining in My Heart” and “True Love Ways”. Additionally, he split with Norman Petty – who still owed Holly money – and the Crickets.

For Christmas 1958, Holly vacationed with family in Lubbock and hung out with Waylon Jennings, whom Holly convinced to join him on a tour being promoted as the “Winter Dance Party” tour. Holly and Jennings flew to New York for meetings about the tour and then met the rest of the troupe in Chicago.

Waylon and Buddy

From the outset, the logistics of the tour were a mess. Amazingly, the organizers of the Winter Dance Party did not take into account the amount of travel time between concert venues and additionally the means by which they planned to traverse these miles were less than ideal. The two tour buses used were constantly without heat and breaking down. Things got so bad that at one point the drummer Holly was using, Carl Bunch, had to be hospitalized for frostbitten toes. Holly was fed up and decided to seek other means of transportation.


In Iowa on February 2nd, Holly chartered an airplane that would take he and his band ahead to the next tour stop in Michigan. The expense was more than worth it to Holly as this would allow them to avoid another frigid trip on the bus, get to the next stop quickly, and give them time to launder their clothes and shower in a warm hotel room. Other performers on the tour were suffering as well and when they caught wind that Holly had chartered a plane, they saw what they thought was a good opportunity.

One of the last photos taken of Holly.

Teen-aged Ritchie Valens asked Holly’s guitarist, Tommy Allsup, if he could have his seat on the plane. Valens and Allsup flipped a coin and Valens won. J.P. Richardson had contracted the flu and asked Waylon Jennings for his seat. Jennings complied. Perhaps miffed that his band was not going to fly with him after taking the trouble to charter the flight, Buddy jokingly said “Well, I hope your ol’ bus freezes up” to which Waylon replied “Well, I hope your ol’ plane crashes”; it was a flip response that would haunt Jennings the rest of his life.

A fan photo of Buddy taken hours before he died.

21-year-old pilot Roger Peterson prepared the plane for take-off with Holly, Valens and the Big Bopper aboard. Light snow was falling and the sky was “obscured”. A report of weather that was “deteriorating” was somehow not relayed to Peterson, who took off normally. The tail lights could be seen by those in the tower, who watched them gradually begin to descend and disappear from sight. Attempts at this point to raise Peterson on the radio were unsuccessful. Later that morning, when still no word had been heard from Peterson, another plane went up to investigate. Less than 6 miles from the airport, the wreckage of Buddy’s plane was spotted in a cornfield.


The plane had hit the ground at a speed of 170 mph “in a nose-down attitude”. Holly and Valens had been ejected and their bodies lay near the wreckage, Richardson’s body had been thrown over a fence into a neighbouring field and Peterson’s was entangled in the wreckage. The cause of death of the three entertainers was cited as “gross trauma to brain”.

Buddy Holly’s pregnant wife heard the news of her husband’s death on television and promptly miscarried Holly’s child. Buddy’s mother learned of her son’s death on the radio, screamed and collapsed. As a result of this tragedy and its effect on family members, authorities implemented a policy to inform the next of kin before publicly announcing a death.

The subsequent investigation into the crash revealed that pilot Roger Peterson was not qualified to fly by instruments only. Additionally, the type of gyroscope that Peterson had been trained on worked in the opposite way to the one on the plane he flew that night. Meaning simply that when Peterson accelerated and thought he was ascending, he was actually descending.


María Elena Santiago-Holly was of course devastated. She did not attend Holly’s funeral and never visited his gravesite in Lubbock. María eventually remarried, had three children and then divorced her second husband. Remarkably, she is still alive as of this writing – aged 87 – and she is a grandmother living in Dallas, Texas. In 2010, María co-founded the Buddy Holly Educational Foundation, a charitable organization that keeps Holly’s legacy alive by funding programs that educate people from all walks of life and social strata in the areas of music in which her late husband excelled including songwriting, production and performance. The list of ambassadors the foundation has is impressive, acknowledging the impact Holly’s career had on so many. They include; Bob Dylan, Paul McCartney, Eric Clapton, Mick Jagger, Keith Richards, Roger Daltrey, Robert Plant, Dave Grohl and Ed Sheeran.

Equally remarkable is the fact that Buddy’s older brother, Larry Holley, is also still with us as of this writing, aged 94. This was confirmed for me by the good people at the Buddy Holly Center in Lubbock: “The Center collects, preserves and interprets artifacts relevant to Lubbock’s most famous native son, Buddy Holly, as well as to other performing artists and musicians of West Texas”. Perhaps the best thing about the center, though, is the fact that I received replies to my inquiries from two separate people there and that was much appreciated. The performance (McCartney played there in 2014) and visual arts center acquired many items from Holly’s estate in 1996 and among the things you can view there are the Fender Stratocaster Buddy played during his final concert and the distinctive glasses he was wearing that fateful night. You can also see his 1958 British Ariel Cyclone motorcycle that was owned by Waylon after Buddy’s death. The center offers free admission and a free trolley tour of Holly-related sites in Lubbock. It is ground zero for any Buddy Holly fan and for any aficionado of early rock ‘n’ roll.

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Waylon Jennings went on to be one of the top performers in country music and an originator of “outlaw country”. He died in 2002. Tommy Allsup opened a bar in 1979 that he called “Heads Up”, a reference to the coin toss that he lost to Ritchie Valens in 1959. Allsup died in 2017, aged 85. Jerry Allison kept the Crickets going for several years and afterwards did session work. Allison is still alive as of this writing, aged 80. John Mueller’s Winter Dance Party “is the official live and authentic re-creation of  Buddy Holly, Ritchie Valens and The Big Bopper’s final tour and the only show endorsed by the Holly, Valens and Richardson estates”. The show has been broadcast on television, has toured extensively throughout the United Sates and Canada and has been performed for the Rock ‘n’ Roll Hall of Fame. The Surf Ballroom – the venue in Iowa where Holly played his last show as part of the Winter Dance Party tour – is still open and operates as a concert venue and museum. In 2009, the Rock ‘n’ Roll Hall of Fame designated the Surf Ballroom as a historic rock ‘n’ roll landmark. The plaque placed there reads, in part; “there are few buildings in existence today that represent a complete shift in our musical history”.


Buddy Holly was truly a unique artist. Not conventionally handsome, not an entertainer with a lot of flash, possessed even of a quirky, hiccuping singing style, Holly nevertheless left an indelible mark on popular music during his all-too-brief career; he spent less than two full years making hit records. Despite the brevity of his arc, he placed 7 songs in the Top 40. More than this, though, he displayed an ambition that makes it clear that he could have been successful in any area of the music business had he lived. He had shown his ability to deftly play his trademark Fender Stratocaster, perhaps best heard in “That’ll Be the Day”. He had proved his innate capacity to craft a rock ‘n’ roll song, writing many of his own hits. He displayed a versatility and a desire to traverse uncharted waters evidenced in part by his stunning acoustic song “Well…All Right”. He ventured boldly into the arena of pop singing with orchestra backing near the end of his career placing songs like “True Love Ways” on the charts. He was a savvy navigator of the business side of music and also was adept at the production aspect of making records; an area I feel he would have excelled in throughout the 1960’s.

He was an innovator and has been called “the single most influential creative force in early rock and roll” with Rolling Stone Magazine placing him at #13 on its list of the “100 Greatest Artists”; think about that – only 12 other artists have made more of a mark than Buddy Holly did and he was at it for only 20 months. Let’s break it down; who beat Holly on this list? The Beach Boys, still going, almost 60 years. Bob Marley, 9 years. Ray Charles, 51 years. Aretha Franklin, 62 years. Little Richard, 4 years of hit-making. James Brown, 50 years. Jimi Hendrix, 4 years. Chuck Berry, 25 years making records. The Rolling Stones, still going, almost 60 years. Elvis Presley, 23 years. Bob Dylan, still going, almost 60 years. The Beatles, 9 years. And #13 Buddy Holly. 1.75 years. It boggles the mind.


John Lennon and Paul McCartney studied Holly’s style and were inspired by him to name their band after an insect. Sir Paul owns the rights to Buddy’s catalogue. 17-year-old Bob Dylan saw Holly in concert two nights before Holly’s death. Dylan says that night Holly looked at him. Bob mentioned Holly’s influence when he was accepting the Grammy for Album of the Year, 39 years later. Keith Richards modelled his guitar playing in part on Holly’s “Not Fade Away”, a song the Rolling Stones recorded in 1964. “He’s in everybody”, Richards has said of Buddy. Don McLean immortalized Holly in his landmark song “American Pie”, in which he famously referred to Holly’s death as “the Day the Music Died”. At 13 years old – even though he did not need them – Elton John started wearing eyeglasses similar to Buddy’s. The first album Eric Clapton ever bought was The ‘Chirping’ Crickets. He was inspired when he first saw Buddy playing his Fender; “I thought I’d died and gone to heaven…I said to myself ‘That’s the future. That’s what I want'”. Bruce Springsteen – perhaps the most genuine artist in history – has said that playing Buddy Holly’s music “keeps me honest” and apparently, before every concert performance, he will run through “Rave On”, a means by which he can maintain his bearings. Buddy Holly’s influence has far exceeded his time on earth.

Sometimes we get so used to an artist it’s hard to hear their attributes. Do yourself a favour; strip away what you know and listen to Buddy Holly again. For the first time.




  1. This is one of the worst tragedies ever. Buddy was so talented and I always wonder about where he would have gone next in his musical career. It’s disgusting how his family learnt of his death. So awful that his wife lost the baby due to the shock.

    • There is so much that is sad in Buddy’s story. His performing style had enough “quirk” to it that I wonder if he would’ve thrived more behind the scenes. But with his talent and with the way music changed in mid-60’s, you could easily imagine him coming back as a recording artist and making some serious statements. There is a piece of “fan fiction” in this, for sure. Someone could write a “what if?” scenario.

  2. Another superb piece. The brutality of the music and entertainment business never ceases to leave me scratching my head. I saw in a recent doc that the surviving members of the tour, just kids really, never even got a night off following the crash, and were told to basically carry on as if nothing had happened. Some or all of the tour participants weren’t even paid at the end.

    This is a major digression, but have you seen the latest dust up within the Beach Boys? Al and Brian have condemned a planned show by the ‘official’ Beach Boys (Mike and Bruce) at a trophy hunters’ convention in Reno, and have even supported an online boycott petition. So far, I think Mike is unmoved, but I guess we’ll see how strong the backlash is. Deeply disappointing (although sadly perhaps not surprising) that Mike’s Beach Boys would lend their support to this kind of thing.

    • “Brutal” is a good way to describe the “business” side of show business. And, no, I hadn’t heard of this latest BB beef. Another digression is James Dean – never got fat, never made a bad movie. Sometimes when a thing goes on and on and on it can put a stink on something that was wonderful. “James Bond” is old enough now that people want to see major changes and minor controversy is stirred up. Longevity – in anything – can be a curse. Brian and Mike will be 80 soon. Sad. Why can’t everything be like Rebel Without a Cause and Smiley Smile?

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