On February 13, 2002, Waylon Jennings ended his battle with diabetes.  Kris Kristofferson once mentioned that Waylon was a “the bad guy with a big heart.”

Waylon Jennings had one child since his marriage to Jessi Colter in 1969 despite having five other children from 3 previous marriages. His son, Waylon Albright “Shooter” Jennings followed his footsteps as he played in numerous band and released an album in October 2008 containing his father’s different recordings before his death.

Struggles

Early in his career, Waylon Jennings was deeply into the use of drugs. His addiction escalated to the use of expensive cocaine and amphetamine habit which would cost him thousands of dollars on average. Waylon decided to stop using drugs in 1984.

In the following year, Jennings together with Kris Kristofferson, Johnny Cash, and Willie Nelson, came together and formed Highwaymen. They immediately made a splash with their song Highwayman” that became a part of their album with the same title. Unfortunately, their second album “Highwayman 2” didn’t catch that much of attention.

Waylon Jennings had a hard time getting his songs played on country music stations. Nonetheless, Jennings still made a name for himself with live performances and concert tours until 1997. He was even featured on some of the shows in Lollapalooza tour in 1996 where he performed acts that showcased his alternative rock style. It was during this time too that Jennings released his book, “Waylon: An Autobiography,” which shared his many ups and downs.

Jennings also had his share of struggles with health when he was diagnosed with diabetes in early 1990. This caused Jennings to have trouble walking in his later years. This didn’t stop him from creating music. In 2002,  Jennings made several performances at the Ryman Auditorium in Nashville Tennessee for his album “Never Say Die Live.”

He was soon inducted to the Country Music Hall of Fame in 2001. In the same year, Jennings had to have a foot amputated because of diabetes and his poor health.

Crossover Success

Are You Sure Hank Done It This way” was Waylon Jennings’ first taste of Crossover success. The song made an appearance on the Pop charts. He was also honored by the Country Music Hall of Fame as the Male Vocalist of the Year. Jennings also contributed to the music compilation Wanted! The Outlaws in 1976. This helped him make a bigger name in the music industry. The album peaked at number one on the Pop album charts.

Jennings also had collaborations with Willie Nelson and recorded “Waylon and Willie” in 1978. This went on and sold for millions of copies. This featured Mammas Don’t Let Your Babies Grow Up Like Cowboys, one of the duets in the album that reached the top of the charts and earned Jennings his second Grammy Award. He and Nelson shared the honors for Best Country Vocal Performance by a Duo or Group.

For the next couple of years until the ‘80s,  Waylon Jennings continued to make hits including, “Luckenbach, Texas (Back to the Basics of Love)” and  the theme song for ‘The Dukes of Hazzard’ (Good Ol’ Boys).”  In addition to recording the televisions show’s theme song, Jennings also was the narrator for the country Comedy “The Dukes of Hazzard.”

Country Fame

In 1965, Waylon Jennings moved to Nashville. He became roommates with The Man In Black of Country music, Johnny Cash. This marked their life long friendship. In the same year, Jennings had his first country hit with “Stop the World (*And Let Me Off).” The following year, Jennings had several successful singles, which included “Walk On Out of My Mind” and “Only Daddy That’ll Walk the Line.” This led to Jennings winning his first Grammy Awards in 1969 for Best Country Performance by a Duo or Group with the group “MacArthur Park”, which he recorded with the Kimberlys.

Throughout his career, Waylon Jennings continued to redefine his music. He was known to produce a tougher, more bass-driven sound. He worked on songs that was written by songwriters such as Kris Kristofferson and Willie Nelson.

In 1973, Waylon Jennings released Honky Tonk Heroes, which was one of the songs that introduced the new style of so-called outlaw sound. Jennings also released top charted songs “This Time” and I’m a Ramblin’ Man.”