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On the Road Again: How Country Star Willie Nelson has Stayed Cool Since the 50s

Jerry Byers
 Photo by Larry Philpot CC BY 2.0
Photo by Larry Philpot CC BY 2.0

In a career that began in 1956, Willie Nelson has been one of the most iconic performers and personalities in American pop culture. The timeless musician who worked as a disc jockey early in his career has been transformed many times during his 60 plus year career, becoming one of the “coolest cats” in music according to one musician.

Just how cool is Willie Nelson?

Nelson was a member of the Grand Ole Opry in the 1960s and wrote songs for artists like Roy Orbison, Billy Walker, and the biggest jukebox hit of all time, “Crazy” by Patsy Cline.

Willie Nelson and his guitar ‘Trigger’, performing at Cardiff on January 25, 2007. Photo by Robbiework CC BY-SA 3.0

Willie Nelson and his guitar ‘Trigger’, performing at Cardiff on January 25, 2007. Photo by Robbiework CC BY-SA 3.0

In the 70s, Nelson helped create a whole new music genre called “Outlaw Country” in Austin, Texas and combined his country background with the hippie scene to massive popularity. Willie started his 4th of July picnic concerts in the early 70s, and was featured on the first Austin City Limits TV show in 1974. He toured the south raising money for PBS stations to promote live broadcast of the show on public broadcasting stations.

Nelson performing on a Grand Ole Opry show in 1965

Nelson performing on a Grand Ole Opry show in 1965

Nelson even has a street named after him in Austin and is a member of the Country Music Hall of Fame; he is on Rolling Stone’s list of 100 greatest singers, and was even inducted into the National Agriculture Hall of Fame for his charitable work with Farm Aid (a concert series that donated proceeds to independent farmers). He is an activist that puts his money and effort where his mouth is. He has his own bio-diesel fuel bearing his name – Bio-Willie – which is produced from soybeans as an alternative to fossil fuels.

Willie Nelson and Dolly Parton

Willie Nelson and Dolly Parton

Additionally, he is the co-chair of NORML which advocates for the reform of “pot” laws and boasts his own legalized brand of it named “Willie’s Reserve”. Artists from rapper Snoop Dogg to country star Toby Keith to actor Seth Rogen have all marveled at Willie’s dedication (and seemingly superhuman strength) in consuming it.

Singer-songwriter Willie Nelson, performing during the Country Throwdown Tour in 2011. Photo by BSC Photgraphy CC BY 2.0

Singer-songwriter Willie Nelson, performing during the Country Throwdown Tour in 2011. Photo by BSC Photgraphy CC BY 2.0

Nelson was the honorary chairman on the board of the official Texas Music Project and was in one of the coolest bands ever – The Highwaymen. The band included Willie, Johnny Cash, Waylon Jennings, and Kris Kristofferson and toured the world in the 1980s.

Willie Nelson has done duets with Julio Iglesias, Merle Haggard, Ray Charles, Neil Young and even First Lady Rosalynn Carter. He also sang on the seminal “We Are the World”, along with a plethora of other music stars, which benefited Africans suffering from famine.

Kris Kristofferson, Willie Nelson, and Waylon Jennings at the 1972 Dripping Springs Reunion

Kris Kristofferson, Willie Nelson, and Waylon Jennings at the 1972 Dripping Springs Reunion

And of course you can’t leave out what is possibly the greatest road trip song in existence. Willie’s 1980 hit “On the Road Again” which has been covered numerous times by other acts.

One of Willie’s most famous trademarks is his trusty guitar, named Trigger, one that he used for nearly 40 years. It is a 1969 Martin N-20 nylon-string classical acoustic guitar which he amplifies to get his particular “Willie” sound. Nelson based his style and sound of that of legendary jazz guitarist Django Reinhardt.

Nelson’s guitar, Trigger, has been signed by several of his friends. Photo by Paul Familetti CC BY 2.0

Nelson’s guitar, Trigger, has been signed by several of his friends. Photo by Paul Familetti CC BY 2.0

He has released an astounding 68 studio albums, a couple of Christmas albums, a dozen live albums, two movie soundtracks, over 40 compilation albums, and collaborated on 34 others. Over a dozen of his albums have reached No. 1 on the U.S. charts. His hit singles have produced similar results with 25 No. 1 billboard hits in the U.S. and 33 internationally with huge audiences in Australia and New Zealand besides the U.S.

In 2008, Nelson reopened the truck stop Willie’s Place near Hillsboro, Texas. Photo by Billy Hathorn CC BY 3.0

In 2008, Nelson reopened the truck stop Willie’s Place near Hillsboro, Texas. Photo by Billy Hathorn CC BY 3.0

Nelson’s long time manager failed to pay any income taxes for several years leaving him with a $32 million tax liability in the 1990s. After negotiating with the IRS, he released an album aptly named, “The IRS Tapes: Who’ll Buy My Memories” and liquidated other assets to pay off the debt.

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He has appeared in over 40 films and television shows including The Electric Horseman, Honeysuckle Rose, Barbarosa, and The Simpsons. His songs have been featured in many more.

Willie Nelson at Farm Aid, 2009. Photo by Larry Philpot CC BY 2.0

Willie Nelson at Farm Aid, 2009. Photo by Larry Philpot CC BY 2.0

Perhaps one of the craziest things that Willie Nelson has done is the much-documented event where he partook in his favorite substance on top of the roof at the White House during the Carter administration – with the son of the U.S. President, Chip, no less.

Read another story from us: The Iconic Love Story of Johnny Cash and June Carter

Nelson commented about the incident on Sam Robert’s Show on SiriusXM radio saying, “It doesn’t get any better than that.”

Correction: In the original version of this article we stated “Nelson helped produce and create one of the greatest live music festivals in the U.S. – Austin City Limits – way back in 1973.” This is not entirely accurate and we replaced it with “Willie started his 4th of July picnic concerts in the early 70s, and was featured on the first Austin City Limits TV show in 1974.” The correction was made on 4/25/19.

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