Waylon Jennings died Wednesday at the Chandler, Ariz., home he shared with his wife, singer Jessi Colter. He was 64.
The news came just weeks after the singer's publicist announced the December 2001 amputation of Jennings' left foot due to complications associated with diabetes.
No one would have guessed then that the seemingly routine announcement was the precursor to the legend's death six weeks later.
"My heart is broken," said singer Travis Tritt upon hearing of Jennings' death. "He represents everything I admire and respect in an artist and a person. Doing things his own way, speaking his mind regardless of the consequences and reaching out and touching the true inner feelings of his audience are all things Waylon stood for throughout his career."
Jennings' career began in the mid-1950s when he went to work as a disc jockey at a Texas radio station. A chance meeting with Buddy Holly at the station in 1955 led to Holly eventually producing Jennings' first album and hiring him for his band.
Jennings escaped the February 1959 plane crash that killed Holly, Ritchie Valens and J.P. Richardson (The Big Bopper).
In his 1996 memoir, "Waylon: An Autobiography," Jennings provided the most complete accounting of how he gave his seat on the plane to Holly and joined other members of the band on a bus following a concert that night.
He said he and Holly had engaged in a good-natured argument about the seat, and he settled it by telling Holly to go ahead and take the seat, joking that he hoped "your ol' plane crashes."
Herb Alpert signed Jennings to A&M Records in 1963 for a brief and unsuccessful stint. In 1965, Chet Atkins gave Jennings a record deal with RCA, the label that Jennings would struggle with for the next 20 years.
"For Waylon, it was always about the music," said Joe Galante, chairman of RCA Label Group. "The only spotlight he ever cared about was the one on him while he was onstage. It wasn't about the awards or events. He was an original and a pioneer in terms of creating his own sound. This is a great loss for the music world."
Jennings abhorred music awards, often winning but seldom appearing in person to accept them. During his career, he won two Grammy Awards and four Country Music Association Awards, including the 1975 male vocalist of the year honors.
In October 2001, Jennings was inducted into the Country Music Hall of Fame. His son, Buddy "Shooter" Jennings, accepted on his behalf.
"I'm so proud I got to call his name out and induct him into the Hall of Fame," Marty Stuart said in The Tennessean. "And I'm so proud he didn't show up. It would have broke my heart if he'd have showed up."
For many, Jennings always will be known for "Mamas Don't Let Your Babies Grow Up To Be Cowboys," a No. 1 duet he performed in 1978 with fellow "Outlaw" Willie Nelson. For others, his role as the singer of the theme song to the popular show "Dukes of Hazzard" has cemented his place in posterity.
Those milestones, however, are just bullet points of a 47-year career that includes 66 albums and 13 No. 1 singles. He was also famous for recording stints with fellow legends Nelson, Kris Kristofferson and Johnny Cash, known collectively as The Highwaymen.
"Waylon was a dear friend, one of the very best of 35 years," Cash said of Jennings. "I'll miss him immensely."