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  • Sep 10, 1958
    Waylon Jennings has his very first recording session in Clovis, New Mexico, with Buddy Holly producing. He records "Jole Blon"
    Oct 21, 1958
    Buddy Holly records "True Love Ways," "Raining In My Heart" and "It Doesn't Matter Anymore" at Pythian Hall in New York. "True Love Ways" becomes a country hit for Mickey Gilley in 1980
    Oct 25, 1958
    Don Gibson sings "Give Myself A Party" on ABC's "The Dick Clark Show." Also on the bill are Frankie Avalon and Buddy Holly
    Oct 28, 1958
    Buddy Holly holds his final recording session, three months before he dies in a plane crash. Holly had become the first person to produce Waylon Jennings, and his song "True Love Ways" would later become a country hit for Mickey Gilley
    Dec 1, 1958
    Maria Elena Holly gives her husband, "True Love Ways" songwriter Buddy Holly, a gold watch for an early Christmas present. Barely two months later, the timepiece is found in the rubble of his fatal plane crash
    Dec 31, 1958
    Buddy Holly anonymously plays drums for country piano player Moon Mullican at a New Year's Eve show in Odessa, Texas
    Jan 23, 1959
    Buddy Holly performs in Milwaukee, where the temperature is 25 below, sharing the bill with Ritchie Valens, Frankie Sardo, The Big Bopper and Dion. Waylon Jennings plays bass for Holly on what proves to be the first date on Holly's final tour
    Jan 31, 1959
    Buddy Holly performs in Duluth, Minnesota, during what proves to be his final concert tour, with Waylon Jennings playing bass guitar. In the audience: Bob Dylan and future country record producer Jimmy Bowen
    Feb 2, 1959
    Buddy Holly plays his final concert, using a band that includes Waylon Jennings and Tommy Allsup, at the Surf Ballroom in Clear Lake, Iowa. It's also the last show for J.P. Richardson (The Big Bopper) and Ritchie Valens
    Feb 3, 1959
    Rock pioneer Buddy Holly dies in a plane crash near Mason City, Iowa, along with touring partners The Big Bopper and Ritchie Valens. Holly's bass player, Waylon Jennings, gave up a seat on the plane

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