The Tragically Short but Influential Career of Buddy Holly (Part 2 & 3, August 14, 2023) — East Texas Historical Association
Gary L. Pinkerton
Buddy Holly had left Lubbock, recorded music in Nashville, and participated in a tour, but less than a year after having what seemed like good fortune, he was stuck in limbo. Decca had informed him that they were not going to proceed with any more recording sessions with “Buddy Holly and the Two Ton
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East Texas Historical Association
Buddy Holly had left Lubbock, recorded music in Nashville, and participated in a tour, but less than a year after having what seemed like good fortune, he was stuck in limbo. Decca had informed him that they were not going to proceed with any more recording sessions with “Buddy Holly and the Two Tones,” but they also forbade Holly from entering into any agreements with other companies. Holly was confident that he had the right formula for success in the day’s music scene, but he had no desire to be under the thumb of the Nashville or any other “establishment” regimes. What he needed to do was find a place where he could record the music he wanted to play.

Holly returned to Lubbock after he finished the tour with Faron Young and almost immediately reached out to Norman Petty, a promoter and act manager who lived in Clovis, New Mexico, just about a hundred miles northwest of Lubbock. Petty, who also owned a studio, had produced and promoted two 1956 hit records, Buddy Knox’s “Party Doll” and Jimmy Bowen’s “I’m Sticking with You.” He had marketed both records as part of the “rockabilly” sound, which is what some people had begun to call the new hard-driving rhythms that were combined with lyrics that were closer to the country records of the day. Petty agreed to provide studio time for Holly, so he recruited Allison and Welborn once again and added Niki Sullivan to play rhythm guitar. Holly would sing and play lead guitar. The group recorded a demo of a song that Holly had written and composed titled “That’ll Be the Day,” which he had recorded for Decca in Nashville but they had not pressed or released. Petty was impressed and quickly offered to manage and promote the group.

Petty sent the demo to smaller Brunswick Records, a New York City based company. Brunswick recognized the unique sound the group had put together and offered a contract and recording time. There was a small problem, however—that nagging stipulation from Decca that kept Buddy Holly from recording with another company. Brunswick executives found a work around; they would market the new record under a different group name. Jerry Allison suggested they be called “The Crickets,” and that is what Brunswick went with. Brunswick agreed to release “That’ll Be the Day” with no additional production or recording and also signed The Crickets to a contract which gave Holly complete artistic control. They did have The Crickets come to New York and record “I’m Looking For Someone to Love” as the B-side to the record.

When The Crickets arrived in New York, an attorney discovered an even better loophole for Brunswick. It seems that since Brunswick was actually a subsidiary of the Decca Records Corporation then they could legally use the name “Buddy Holly.” Brunswick decided that for the first record they would use just The Crickets, but they then recorded the group under the label of another subsidiary, Coral Records, and marketed those recordings as “Buddy Holly” as a solo act. “That’ll Be the Day” hit the streets on May 27, 1957. The record debuted the R&B charts #25 in early June, which led promoter Irvin Feld to contact Petty and book Buddy Holly and the Crickets on a summer tour to Washington D.C., Baltimore, and New York City. The group was set to play venues that usually booked what was then termed “race music” acts, which meant most of the performers were African American, as was the majority of the audience. The band’s first appearance was at the famed Apollo Theater in the Harlem neighborhood of New York City. During their first show the audience did not seem to be impressed, but Holly added some covers of current Black musician’s music and subsequent crowds warmed to the band.

At the same time Buddy Holly and the Crickets were touring, “That’ll Be the Day” began to climb the charts. Petty immediately began to put together other music Holly and the band had made in Clovis so that Coral could release a full album. Buddy Holly and The Crickets also were invited onto “American Bandstand,” hosted by Dick Clark, which provided even greater visibility. “That’ll Be the Day” reached #1 on the U.S. charts in September and had also topped the UK charts by the next month. That summer, Coral also released “Peggy Sue” with “Buddy Holly” as the only credited performer. It rose quickly to #3 on the Billboard charts. The band finished their Feld-arranged tour in September and went back to Lubbock to assess their futures.

The trip back to Texas would be a turning point for Buddy Holly and the Crickets. Petty had the band go to Oklahoma City to record another album. Petty dubbed and post-produced the recording in Clovis and named the album “The ‘Chirping’ Crickets,” and Coral would release singles of “Oh Boy!” with “Not Fade Away” on the B-side. “Peggy Sue” peaked at #10 on Billboard, which was enough for Ed Sullivan to book the group on his nationally broadcast show in December 1957. When they finished performing on the Sullivan Show, Niki Sullivan decided to leave the band and return back to enroll at Texas Tech. The group would then go on a national tour with a number of replacements playing in Sullivan’s spot. When the tour ended in May, 1958, Holly hired Tommy Allsup to play lead guitar and the band prepared to record more music in Clovis. Buddy Holly had, almost overnight, become a national star.

Buddy Holly’s hits with “That’ll Be the Day” and “Peggy Sue” had hit a nerve with the American public and his fans clamored for more, which meant he had to feed that appetite. Subsequently, that meant more appearances and also more recordings. He and his band joined a new tour, “America’s Greatest Teenage Recording Stars” in January 1958, and in the same month he made his second appearance on the “Ed Sullivan Show.” He then departed for a tour in the United Kingdom where he played an amazing fifty shows in just twenty-five days. Coral released his debut solo album, “Buddy Holly” while he was in Europe, and it almost immediately began to climb the charts.

He came back to Lubbock in May and once again persuaded Tommy Allsup to permanently join the Crickets, but this time to replace him as lead guitarist, which would give Holly more time to sing and also write more songs. Norman Petty arranged a new recording session in Clovis, where they recorded “It’s So Easy” and “Heartbeat.” When the recording session finished, Holly hopped on a plane and went back to New York to oversee post-production, and record new music without the Crickets as a back-up band. He hired some jazz-oriented R&B musicians to be studio musicians behind him and recorded “Now We’re One” as well as a cover of Bobby Darin’s “Early in the Morning.”

When he was in New York, his personal life also underwent a huge transformation. Holly had dated his high school girlfriend off-and-on since he was seventeen, but that relationship ended in late 1957. He had to pay a visit to the music publishing house of Peer-Southerland in New York to discuss the rights to songs he had written. While there he met María Elena Santiago, who worked in the office. Smitten, Holly asked her out on a date and actually proposed marriage on that first date. Santiago demurred in her answer, but she kept seeing Holly and he persisted on asking her to marry him. Finally, she agreed, and they married on August 15. Some popular gossip has often spread the rumor that Holly’s family had disapproved of the marriage, which is false. The person who did not like the fact that Buddy Holly had gotten married was Norman Petty. Petty believed that much of Holly’s appeal was to his female fans and the fantasy that he was “available.” Marriage would pierce that image, so he implored Holly to keep his marriage to Santiago secret. However, Petty’s objections may have had another genesis. Santiago was an experienced business administrator and when she began to look over Holly’s finances, she noticed what she thought was an irregularity. It seemed to her that Petty was retaining royalties and tour profits—labeled as “expenses”—that rightfully belonged to Holly. She brought that to her husband’s attention and Holly—who despite his record sales and fame was barely breaking even as an act after paying recording expenses and his bandmates—planned to confront Petty and remove him as his manager.

In the interim, Holly returned to Clovis to record new music. He also hired a new member of the band. Holly had met a young Lubbock disc jockey named Waylon Jennings the year before when he was home,. Jennings was also attempting to enter the music business and Holly agreed to pay for and produce a recording session for him. He also convinced Jennings to join his band as a guitarist. When he finished the Clovis session, Holly returned to New York and did more recording, this time with innovative strings and orchestral arrangements. He produced four songs in these “string sessions,” including “True Love Ways,” which he had written for Santiago, and the Paul Anka song “It Doesn’t Matter Anymore.” Finally, in December 1958 he informed Petty that he was terminating their relationship and that he was moving permanently to New York. The split was actually amicable as Petty realized that logistically—since Holly would be in New York—and artistically, Holly had moved beyond what Petty could offer. Also, Allison decided that he was through with touring and when he left the name of The Crickets was also retired.

Holly put together a new band, with Jennings on lead guitar, Allsup playing rhythm and Carl Bunch on the drums. The new group gathered and practiced for a bit in New Yorks and then, on January 21, 1959, boarded a train and joined a new tour, the “Winter Dance Party.” The tour was to travel throughout the Midwest, which was a difficult trip in the dead of winter. The buses they traveled on were unheated and also regularly broke down, stranding the party sometimes for hours in intense cold. After one such incident, Carl Bunch had to be hospitalized with frostbite in his toes—which in the end would actually save his life.

The tour had a scheduled stop in Clear Lake, Iowa on February 2 and Holly wanted no part of another ride on a cold bus. So, he contacted a charter air service to fly him, Jennings, and Allsup to their next stop in Moorhead, Minnesota. The band, along with rising star Ritchie Valens and J.P. Richardson, a Beaumont DJ whose stage name was “The Big Bopper,” played a sold-out show in Clear Lake and just after midnight began to pack up and prepare to leave. Richardson, who had been ill with the flu for more than three days and performing left him exhausted, begged Jennings to let him take his seat on the plane. Jennings agreed. Valens wanted Allsup’s seat, and the guitarist agreed to a coin flip to see who boarded the plane. Valens won and four people, Holly, Richardson, Valens, and the pilot boarded the small Beechcraft plane for a flight to Fargo, ND and then on to Moorhead.

They never made it. The plane had a new gyroscope that the pilot was unfamiliar with. Confused as to the horizon on the dark early morning of February 3, 1959, the plane plowed—at almost full speed—into a cornfield just outside of Clear Lake. There were no survivors. Buddy Holly was dead at just 22. Holly was buried in his hometown; the pall bearers included Sonny Curtis and Allison. María Elena Santiago’s grief led to a miscarriage. As for Holly, his life ended but his influence lived on. Singles released posthumously, one of which was “True Love Ways,” topped the charts. Later rock groups, most notably The Beatles, listed Holly as one of their greatest influences. The tall, thin young man from Lubbock lived a short, but significant life.

The East Texas Historical Association provides this column as a public service. Scott Sosebee is a Professor of History at Stephen F. Austin State University and the Executive Director of the Association. He can be contacted at sosebeem@sfasu.edu; www.easttexashistorical.org.