Waylon Jennings Through The Years: From His Younger Days Through Outlaw Infamy

Young Waylon

(Michael Ochs Archives/Getty Images)

Jennings’ regional acclaim dated back to childhood appearances in talent shows. It put him on the map of local product turned rock ‘n’ roll pioneer Buddy Holly, who had a hand in Jennings’ 1958 debut single, “Jole Blon” b/w “When Sin Stops (Love Begins).” Holly recruited Jennings to play bass on the rocker’s Winter Dance Party tour, which got cut short by the 1959 plane crash that claimed the lives of Holly, Ritchie Valens and the Big Bopper (J.P. Richardson).

The first signs that Jennings was destined to become a country star came in Arizona, where he and the original lineup of his backing band, The Waylors, built an audience for its rock-influenced, guitar-driven brand of country music: a sonic approach influenced by Elvis Presley, George Jones and Hank Williams.

Despite landing a deal with A&M Records by 1963 (and first recording future classic “Just to Satisfy You” in 1964), early career victories eluded Jennings. In 1965, he joined the RCA Victor roster, where he found chart success (1968’s “Only Daddy That’ll Walk the Line” reached No. 2 and teased the shape of outlaw country to come) and won a Grammy (Best Country Performance by a Duo or Group With Vocal for The Kimberlys collaboration “MacArthur Park”).  Still, the young, clean-shaven singer, songwriter and guitarist was yet to fully realize his outlaw country potential.

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