Waylon Jennings was born in Littlefield, Texas. He began playing music at the age of 8 when his mother taught him how to play guitar. By the time he was 12, he was performing on the radio for KVOW in Littlefield, Texas, where he later worked as a disc jockey.
In 1958, Jennings moved to Lubbock, Texas and worked for KDAV radio, where he met Buddy Holly. Jennings made his first recordings that year, "Jolie Blon" and "Where Sin Stops (Love Begins)," with Holly backing him on guitar. Later, Holly hired Jennings to play electric guitar for his Winter Dance Party Tour. In a twist of fate, Jennings gave up his seat on the plane that crashed in Clear Lake, Iowa on February 3, 1959. Holly, Ritchie Valens and J.P. Richardson, better known as the Big Bopper, were killed. Richardson had complained of having to ride on the bus while having a cold, so Jennings switched places with him. In an interview with NPR, Jennings said it was his first experience with someone close to him dying and "it took me quite a while to get over it."
Jennings released his debut album, Folk-Country, in 1966 for RCA records. He had modest success in the late 1960s, including the hit single "Just to Satisfy You." It was after meeting Willie Nelson that he became part of the Country outlaw sound. His duet with Nelson, "Luckenbach, Texas," was a hit in 1977, although Jennings confessed he never really liked the song. Nelson and Jennings followed the song up with the album Waylon and Willie, which featured the song that would become a country music standard, "Mama Don't Let Your Babies Grow Up to Be Cowboys." The song was #1 for four weeks on the country charts and won Jennings and Nelson a Grammy award in 1979.
Overall, Jennings had 16 #1 Country singles and several platinum albums. In 1975, Jennings was named Male Vocalist of the Year by the Country Music Association, on the heels of his 1974 release The Ramblin' Man. In the 1980s, he formed the band The Highwaymen with Nelson, Johnny Cash, and Kris Kristofferson. Jennings also lent his distinctive voice to the 1980s television show The Dukes of Hazzard, serving as the show's narrator. He also sang the show's theme song.
In 1993, Jennings issued a children's album, Cowboys, Sisters, Rascals and Dirt, featuring the song "Shooter's Theme." The song was a tribute to his 14 year-old son, Shooter, who went on to develop his own career in country-rock. Shooter played the role of his father in the 2005 movie, Walk the Line, the story of Johnny Cash.
Jennings was inducted into the Country Music Hall of Fame in 2001. After battling drug addiction much of his life, particularly to cocaine, Jennings quit in 1984, primarily to provide a good example to his son. However, years of smoking and drug abuse took their toll. A diabetic, Jennings had his foot amputated in December 2001, then died in his sleep in February 2002 in Chandler, Arizona.