ON FEBRUARY 13, 2002, A 64-YEAR-OLD MAN DIED IN HIS SLEEP AT HIS HOME IN CHANDLER, ARIZONA. His left foot had been amputated fourteen months earlier. He had refused, for years, to let them take it. The doctors had warned him what would happen. He had told them no, and lived as long as he could on the answer. His wife Jessi was there. His son Shooter was twenty-two.It was February. The same month, forty-three years earlier, when Waylon Jennings had given up his seat on a small plane in Iowa. He was born Wayland Jennings in Littlefield, Texas, in 1937. His mother changed the spelling so he wouldn’t be confused with a local college. He had his own radio show at twelve. He dropped out of school at sixteen. By 1958, a kid named Buddy Holly had heard him on the air and hired him to play bass. Then came the Winter Dance Party Tour. Clear Lake, Iowa. February 2, 1959. The Big Bopper had a cold. He asked Waylon for the seat on the chartered plane. Waylon said yes.Holly heard about the swap and joked, “I hope your old bus freezes up.” Waylon shot back: “I hope your ol’ plane crashes.” Hours later it did. Holly was dead. Valens was dead. The Big Bopper was dead. Waylon was twenty-one years old, and he carried that exchange to his grave. He started taking pills not long after. He didn’t stop for a very long time.He survived everything else. The cocaine. The 1977 federal bust where the package somehow disappeared before agents could log it. The bypass surgery. The divorce that almost happened with Jessi and didn’t. Ninety-six charting singles. Sixteen number ones. The Outlaws. The Highwaymen. The black hat that became his whole identity. In October 2001, the Country Music Hall of Fame finally inducted him. He didn’t show up. He sent his son in his place — and what he told that son to say in the acceptance speech is something only the family knows for sure.Four months later, in his sleep, in February — he finally took the flight he’d given away.
Waylon Jennings and the Flight He Never Took On February 13, 2002, Waylon Jennings died in his sleep at his home in Chandler, Arizona. Waylon Jennings was sixty-four years old.…