THE MAN WHO defined the outlaw movement in country music succumbed to diabetes-related health problems on Feb. 13, 2002. Waylon Jennings, the larger-than-life singer, songwriter and guitarist born in Littlefield, Texas, recorded 60 albums and had 16 No. 1 country singles in a career that spanned five decades and began when he played bass for Buddy Holly. He was inducted into the Country Music Hall of Fame in 2001.
In 1959, his career was nearly cut short by tragedy soon after it began. He was scheduled to fly on the light plane that crashed and killed Holly, Ritchie Valens and J.P. the “Big Bopper” Richardson. Jennings gave up his seat on the plane to Richardson, who was ill and wanted to fly rather than travel by bus with those left behind.
With pal Willie Nelson, Jennings performed duets like “Mammas Don’t Let Your Babies Grow Up to Be Cowboys,” “Luckenbach” and “Good Hearted Woman.” Those 1970s songs nurtured a progressive sound and restless spirit embraced later by Steve Earle and others.
He traditionally wore a black cowboy hat and ebony attire that accented his black beard and mustache. Often reclusive when not on stage, he played earthy music with a spirited, hard edge. Combined, Jennings had a well-defined image that matched well with his history of battling record producers to do music his way. About his independence, he once said, “There’s always one more way to do something — your way.” Some of his album titles nourished his brash persona: Lonesome, On’ry and Mean, Nashville Rebel, Ladies Love Outlaws.
He often refused to attend music awards shows on grounds performers shouldn’t compete against each other. He didn’t attend his induction into the Country Music Hall of Fame. And for about 10 years, he declined to appear on the Grand Ole Opry because a full set of drums was forbidden at the time. That rule was eventually dropped. In 1992, he told an interviewer, “I’ve never compromised, and people respect that.”
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