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Waylon Jennings


I’ve been hooked on the collaboration of Waylon & Willie and their outlaw country music for a long time.

And, I’m glad I ran across this image and am honored to have worked with photographer Kirk West of Macon, GA on this Waylon Jennings piece.

Waylon Jennings was born on June 15, 1937 and was an American singer, songwriter, musician, and actor. Jennings began playing guitar at 8 and began performing at 12 on KVOW radio. His first band was The Texas Longhorns.

In 1958, Buddy Holly arranged Jennings’s first recording session, and hired him to play bass. In Clear Lake, Iowa, Waylon gave up his seat on the ill-fated flight that crashed and killed musicians Buddy Holly, the Big Bopper, Rich Valens & pilot Roger Peterson. The day of the flight was later known as The Day the Music Died.

Jennings then worked as a D.J. in Coolidge, Arizona, and Phoenix. He formed a rockabilly club band, The Waylors and recorded for independent label Trend Records and A&M Records, before succeeding with RCA Victor after achieving creative control.

During the 1970s, Jennings joined the Outlaw movement. He released critically acclaimed albums Lonesome, On’ry and Mean and Honky Tonk Heroes, followed by hit albums Dreaming My Dreams and Are You Ready for the Country. In 1976 he released the album Wanted! The Outlaws with Willie Nelson, Tompall Glaser, and Jessi Colter, the first platinum country music album. That success was followed by Ol’ Waylon, and the hit song “Luckenbach, Texas”. Waylon joined the country supergroup The Highwaymen with Willie Nelson, Kris Kristofferson, and Johnny Cash. During that period, Jennings released the successful album Will the Wolf Survive.

 On February 13, 2002, Jennings died from complications of diabetes.

Jennings also appeared in movies and television series. He was the balladeer for The Dukes of Hazzard; composing and singing the show’s theme song. In 2001 he was inducted into the Country Music Hall of Fame, which he chose not to attend. In 2007 he was posthumously awarded the Cliffie Stone Pioneer Award by the Academy of Country Music.

I had a lot of fun painting this portrayal of Waylon, and I hope he finds a way into your home, as his music has.

I’m proud to announce and give credit to photographer Kirk West for collaborating with me on this painting.


 (View Painting Process)

This reproduction has an image area of 19” x 27”(48.3 cm x 68.6 cm) with a Limited Edition of 250 prints.

The print price is $379 plus shipping. (Note, the copyright image will not appear on your print)
You can purchase this print now by clicking the Buy Now button.

One comment

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    December 18, 2015 7:28 amPosted 4 years ago
    Chuck Stanley

    This print is AMAZING! it takes me right back to my days growing up and listening to Waylon! I received today, several prints that I purchased- including an extra Waylon print for Mom & Dad who introduced me to his music. Simply amazing!!
    Tom you are a truly gifted artist and a heckuva nice guy! Thanks again and I cannot wait to talk more about the next set of prints on my wish list!


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