Waylon Jennings: Heartbreak, Hard Luck, and an Unbreakable Spirit
Waylon Jennings sang about heartbreak, hard luck, and hard choices — and he knew every one of them firsthand. His life was a mix of triumph and tragedy, shadowed by near misses, personal struggles, and a constant fight to keep going.
In 1959, Jennings’ career was just taking shape under the guidance of Buddy Holly, who invited him on tour alongside Ritchie Valens and The Big Bopper. On February 2, Holly chartered a plane to Fargo, North Dakota. Jennings gave up his seat to the flu-stricken Big Bopper and boarded the bus instead. Holly jokingly said, “I hope your ol’ bus breaks down,” and Jennings replied, “I hope your ol’ plane crashes.” Hours later, the plane went down, killing everyone on board — a moment that haunted Jennings for the rest of his life.
His personal life before meeting Jessi Colter in 1969 was turbulent — three failed marriages, self-destructive habits, and a deep depression. Jessi became his anchor, but not before he nearly destroyed himself with addiction. In the 1970s and ’80s, cocaine took over his life, costing him his health, money, and even briefly his marriage. His habit reached $1,500 a day, and in 1977 he was arrested in a Nashville studio with enough cocaine to face charges of intent to distribute. He finally quit in 1984, flushing $20,000 worth down the toilet and never looking back.
Jennings was no stranger to financial trouble either. Despite earning millions as a top country star, he went broke three times. His generosity and oversized touring entourage drained his resources, and in 1981 he filed for bankruptcy with $2.5 million in debt.
Years of smoking and hard living took their toll. In 1988, Jennings underwent triple-bypass surgery. He quit smoking after 41 years but soon faced another battle: type II diabetes. The disease led to vascular problems, and in 2001, doctors amputated his foot in a last attempt to save his life.
On February 13, 2002, Waylon Jennings died at 64, leaving behind not just a catalog of outlaw country anthems but the story of a man who lived exactly as he sang — recklessly, honestly, and with a heart too big to hide.
His voice may be gone, but the grit, the music, and the legend of Waylon Jennings will always endure.