Waylon Jennings 1985


Waylon Jennings 1985, hand-drawn holding his leather-clad 1954 Fender Telecaster, in Nashville, age 48.

Waylon Arnold Jennings was an American singer, songwriter, and musician. Known for his rough-edged, powerful singing voice, he was also recognized for his “spanky-twang” guitar style with his 1953 Fender Telecaster.

As a teen, Jennings started to work as a DJ in 1956 for the radio station KLLL in Lubbock, Texas and around that time met Buddy Holly while playing local bar gigs. Holly took Jennings as his first artist. He outfitted him with new clothes, and worked with him to improve his image. Holly then arranged Jennings first recording session and hired him to play electric bass for him during his “Winter Dance Party Tour”.
One month into the tour, Jennings gave up his seat on the ill-fated flight on the outskirts of Mason City, Iowa in 1959 that crashed and killed Holly, J. P. “The Big Bopper” Richardson and Ritchie Valens.

In 1967, Jennings rented an apartment in Nashville with Johnny Cash, who later recalled in the Jennings documentary Renegade Outlaw Rebel, “We had a mutual respect for each other as artists, and when we got to know each other we had so much in common: our love for music and, at that time, our love for chemicals.”
While playing 300 days on the road, Jennings and Cash both became addicted to amphetamines, which enabled them to perform during the demanding and sleepless tour circuit. Eventually Jennings became addicted to cocaine, which he finally overcame in 1974.

In 1972, sick with hepatitis, Jennings was hospitalized. During his recovery his manager suggested that Jennings keep the beard that he had grown in the hospital, to match the image of Outlaw Country. This began his classic Outlaw look.
Jennings was instrumental in the inception of Outlaw country movement, and in 1976, recorded country music’s first platinum album, “Wanted! The Outlaws” with Willie Nelson and Jessi Colter.

In 1976, Jennings and his band The Waylors released the album “Are You Ready for the Country” for RCA and released by Chet Atkins.
The album hit number one on Billboard’s country albums three times the same year, topping the charts for 10 weeks.
It was named Country album of the year in 1976 by Record World magazine and it was certified gold by the RIAA.

In the mid-1980s, Johnny Cash, Kris Kristofferson, Nelson, and Jennings formed a successful group called The Highwaymen, the first American country music supergroup.
Their remake of Guy Clark’s “Desperados Waiting for a Train” reached the Top 20. The four starred in one movie together: the 1986 film Stagecoach.

Waylon Jennings hits: “I’m A Ramblin’ Man”, “I’ve Always Been Crazy”, “This Time”, “Dreaming My Dreams With You”, “Only Daddy That’ll Walk The Line”, “Amanda”, the theme song for “The Dukes Of Hazzard”, “Rainy Day Woman”, “Luckenbach Texas”, “Mammas Don’t Let Your Babies Grow Up to Be Cowboys”, “Are You Sure Hank Done It This Way”, “Honky Tonk Heroes”, and “I Ain’t Living Long Like This”.

Late in life, Jennings’s health had been deteriorating for years before his death. Suffering from diabetes, his left foot was amputated at a hospital in Phoenix. On February 13, 2002, Jennings died in his sleep of diabetic complications at the age of 64, in Chandler, Arizona.

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32″ x 40″ stretch canvas print is produced by Giclee printing process and are hand stretched over heavy duty American made white pine. The canvas print is varnished twice after printing. The canvas prints are ready to hang (complete with hanging wire).

Additional information

Weight .25 lbs
Dimensions 16 × 20 × .25 in
Print Size

32" x 40" Stretched Canvas Print $495, 20" x 24" Stretched Canvas Print $330, 11" x 14" Watercolor Print $95, 16" x 20" Watercolor Print $185