“Buddy was the first person to have faith in my music. He encouraged me in my music and my writing. He was my friend. If anything I’ve ever done is remembered, part of it is because of Buddy Holly.”

– Waylon Jennings

Waylon Jennings and Buddy Holly in 1959

“We were best friends.” Waylon Jennings once remarked about his relationship with Buddy Holly. Both men were influential in their own rights, Jennings secured his own recording rights and made music with a stripped-down production style and rock rhythm in the late 1960s to the mid-1970s. By doing this, Jennings changed the direction of country music and indirectly created the outlaw movement (other artists of the movement included Johnny Cash, Merle Haggard and Willie Nelson). Buddy Holly is considered a pioneer in rock and roll music. He influenced such musicians as The Beetles, The Rolling Stones and Bob Dylan. Holly achieved such honors by the age of 22. While Jennings’ career spanned decades, Holly’s lasted less than 5 years. The story of Holly and “The Day the Music Died,” is quite well-known, but what might not be as well-known is friendship between a rock and roll icon and an “outlaw” country performer.

“Winter Dance Party” tour poster

In 1954, Jennings moved to Lubbock, Texas and took a job at KLLL, a local radio station. Both Jennings and Holly had bands and through the various radio station shows, they met each other. On meeting Holly, Jennings remarked, “We just seemed like we were forever running into each other. We got to be friends. We’d hang out when we had a chance.” Holly soon became Jennings’ mentor, helping him produce songs and collaborations.

In late 1958, Holly’s band, the Crickets, needed a temporary bass player for their tour and they turned to Jennings. Besides Holly, the tour also included Ritchie Valens and The Big Bopper (J. P. Richardson). The Winter Dance Party tour was to last for three-weeks with stops all around the Midwest, opening on January 23, 1959. During the tour, the regular tour bus froze up because of the snowy and cold weather conditions. The musicians had to use a school bus with a faulty heater. It was so cold the drummer got frostbite on his feet and had to be hospitalized and the Big Bopper came down with the flu.

After a show in Clear Lake, Iowa, Holly decided to charter a small plane for his band (consisting of himself, Tommy Allsup (guitar) and Jennings.Ritchie Valens and Tommy Allsup flipped a coin for the last seat, Valens won and took Allsup’s seat. Since the Big Bopper was sick, he asked Jennings if he could take his seat on the plane. Jennings said that as long as Holly was okay with it, he was too. When Holly found out Jennings was not going to be on the plane, he jokingly told him, “I hope your ol’ bus freezes up!” Jennings responded back, “I hope your plane crashes!” Those words would haunt Jennings for decades.

The Buddy Holly plane crash site. 5 miles north of Clear Lake, Iowa, February 3, 1959.

Allsup and Jennings got back on the school bus for the cold, long drive to Fargo, North Dakota for the next show. In the early morning of February 3, 1959, the small plane carrying Buddy Holly, the Big Bopper and Richie Valens crashed and all, including the pilot, were killed. February 3rd infamously became known as “The Day the Music Died.”

Jennings felt deeply guilty about his last words to his best friend and it took him a long time to get over it. In 1996, he released Wayon, an autobiography in which he discussed his friendship with Holly. When asked by an interviewer what Jennings meant when he stated that he was probably the closest person to Holly at the end, Jennings stated:

We got close because it was almost as if he had the premonition that he wasn’t going to be around. And he did like me. He liked me a lot and I liked him. We never had a problem. And he tried to help me. He was trying to warn me about things and teach me about music as we went along. He loved music. The last day of his life he was still excited about music and every song he sang. I learned that from him and forgot it periodically: When you do a song, you’ve got to remember you are going to be doing that song for the rest of your life. You better make sure you like it.

Waylon Jennings passed away on February 13^th, 2002 from complications with diabetes.

Here are YouTube links to two of Waylon Jennings’ songs about Buddy Holly:

Sources
http://www.waylonjennings.com/waylon
Interview with Jennings in Sept. 1999 with Gadfly
Buddy Holly & The Crickets website
VH1 Behind the Music:  The Day The Music Dead (YouTube)