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"I did it my way." We associate this lyric with Frank Sinatra, but it describes the career of Waylon Jennings more fittingly. When Jennings passed away on Feb. 13, 2002, he left a legacy of classic songs, hit records, and great guitar playing, but he will be best remembered as a rebel-a man who bucked every trend the fickle music business threw at him, yet succeeded every step of the way.
Jennings was born in 1937 in Littlefield, Texas, and was singing and playing a nylon-- string Stella by age ten. After cutting his teeth on the folk and country music of the day-songs by Jimmie Rodgers, Hank Williams, and Ernest Tubb-Jennings found inspiration in blues artists such as Bobby "Blue" Bland and B.B. King. He fronted his own band by the time he was 13, and worked as a disc jockey at 14.
While still a teenager, Jennings met Buddy Holly, who would produce Jennings' first record, and later hire him as a bassist. (On the infamous flight that claimed the lives of Holly,...