Introduction:
On This Day: Remembering Tommy Allsup, the Guitar Great Who Changed Music History — And Escaped Tragedy by a Coin Toss
On November 24, 1931, Tommy Allsup was born near Owasso, Oklahoma — a date that would mark the beginning of one of American music’s most fascinating and fateful careers. A gifted guitarist whose style bridged Western swing, early rock ‘n’ roll, and classic country, Allsup played alongside the genre’s biggest names, from Buddy Holly to Bob Wills, and later produced music for legends like Willie Nelson and Roy Orbison.
Yet for many, his name remains forever linked to one of the most chilling “what-ifs” in music history: the coin toss that saved his life on the night of the tragic 1959 plane crash that killed Holly, Ritchie Valens, and the Big Bopper.
A Musical Upbringing in Oklahoma
Allsup grew up surrounded by music and took to the guitar early. In high school, he formed a Western swing group, showing a talent well beyond his years. After graduating, he moved through the Oklahoma music circuit, first joining Johnnie Lee Wills and All His Boys in Tulsa before later leading the house band at the Southern Club in Lawton.
His big break came when a friend convinced him to tag along on a trip to Norman Petty’s famed studio in Clovis, New Mexico. Petty was looking for a skilled session guitarist — and Allsup fit the bill instantly. His clean but inventive style soon caught the attention of Buddy Holly, who hired him for recording sessions and ultimately as part of his touring band.
Buddy Holly, the Crickets & the Winter Dance Party
Tommy Allsup made history with Holly, becoming the first guitarist to record a solo on one of his tracks. He joined the Crickets on tour in 1958 and stayed with Holly when the original lineup dissolved, forming a new group with Waylon Jennings and Carl Bunch. Together, they set out on the grueling Winter Dance Party tour in early 1959.
After a performance in Clear Lake, Iowa, Holly chartered a small plane to the next tour stop — a decision that would become infamous. Allsup and Ritchie Valens flipped a coin to determine who would get one of the coveted seats. Valens won. Hours later, the plane crashed shortly after takeoff, killing everyone aboard. Allsup, shaken but determined, continued the remaining shows with the Crickets.
A Prolific Career Behind the Scenes
After surviving one of music’s darkest nights, Tommy Allsup remained deeply rooted in the industry. He became a sought-after session player and later moved into producing. At Liberty Records, he worked on early albums for Willie Nelson and went on to produce projects for Tex Williams, Gene Watson, Mickey Gilley, Asleep at the Wheel, Bob Wills, and more.
Across his lifetime, Allsup’s fingerprints can be found on more than 6,500 recordings — a staggering number that cements his place as one of the most quietly influential musicians of the 20th century.
From Western swing to rock ‘n’ roll to classic country, Tommy Allsup helped shape the sound of American music. And his story — marked by talent, resilience, and a fateful toss of a coin — remains one of the most remarkable in music history.