The Life and Times of Willie

November 17, 2023 5 min read

The Life and Times of Willie

On April 29, 2023, Wille Nelson hit the significant milestone of turning 90. Nelson marked the milestone with a two-night stint at the Hollywood Bowl, joined by artists such as Chris Stapleton, Neil Young, The Lumineers, and Snoop Dogg.

Ninety years old, and he had 60 dates booked in 2023. He had over 60 more in 2022. He’s been playing constantly for a man his age, doing between 100 and 150 dates a year until the COVID-19 pandemic knocked live shows for a loop.

He’s also released over 100 albums, including his solo work, collaborations and live albums. We haven’t even included the singles! His most recent album was Bluegrass, released in September 2023. This album followed I Don’t Know a Thing About Love, released a mere six months earlier in March of 2023!

And that’s just the musical side of things. We haven’t even talked about Willie’s Reserve (yet)...

In his 90 years, he’s hit several career-defining moments that have helped cement his place in the annals of music and pop culture history. Let’s look at some of those moments to celebrate his nine decades.

Early Success as a Songwriter

Nelson had difficulty getting a record deal after moving to Nashville in 1960. His talent as a songwriter didn’t go unnoticed, eventually landing work for Pamper Music. It was during this time that several artists recorded his compositions: “Family Bible,” “Night Life,” “Pretty Paper,” “Ain’t It Funny How Time Slips Away,” and probably most famously “Crazy” (becoming a massive hit for Patsy Cline). 


During this period, Nelson acquired what would be the ubiquitous guitar that followed him throughout his career. A Martin N-20 nylon string fitted with a Prismatone pickup, affectionately known as “Trigger.”

From Country Crooner to Red-Headed Stranger

Nashville wasn’t too kind to Nelson. After securing a record deal, he put out a few singles to little notice, and money wasn’t coming in from sales or touring. Frustrated, he decided to leave Music City for Austin, Texas. 

Austin’s Hippie scene was likely what Nelson needed to get his creativity going again. He went back to performing and writing, combining his songwriting style with elements of country, folk, jazz, and rock and roll into a new sound (creating the blueprint for what would be known as Outlaw Country). Gone were the suits and clean-cut appearance, with hair growing long and the clothes fit for a blue-collar worker. This change in sound and style was a new and rejuvenated Willie Nelson.

The first record introducing this new sound and image was 1973’s Shotgun Willie, followed by 1974’s Phases and Stages, and the 1975 classic Red Headed Stranger. This last one being a concept album about a man on the run after killing his wife, it placed Nelson firmly on the Country music map, as well as earning him the no. 1 spot on Billboard’s Country Music chart for the album and its single “Blue Eyes Crying In The Rain.” 


A Million-Seller

Country music had its audience and was popular with a segment of the population, though it was less mainstream than today. Before 1976, a country record had yet to sell 1,000,000 copies. That was until the world got Wanted! The Outlaws.


The album (released by RCA Records) was a compilation of previously unreleased songs and four new compositions by Willie, Waylon Jennings, Jessi Colter and Tompall Glaser. Released to capitalize on the popularity of the Outlaw Country genre, the record took off, selling a million copies. However, none of the artists on the album were on RCA’s roster at the time (Willie and Waylon had left earlier for different labels). While the record was not entirely Nelson’s, the popularity of the genre and high sales certainly made an impact by introducing him to a much wider audience.

Success Outside the Country Genre With Stardust

Though closely tied to Country music, Nelson was a fan of the Great American Songbook. After the success of Red Headed Stranger and Wanted! The Outlaws, he had the idea to record an album of pop standards (an idea that Columbia Records, his label at the time, really wasn’t enthused about).

With the help of his Californian neighbour Booker T. Jones (of Booker T. and the M.G.s fame), Nelson recorded and released the album Stardust in 1978. Thankfully, his contract with Columbia Records allowed him complete creative control, allowing him to release the album, albeit with little fanfare from the label. Nelson’s instincts, however, were correct. The album took spot no. 1 on Billboard’s Country Music Chart and eventually went 5x Platinum in sales.


Farm Aid

Working as a family farmer with a livelihood dependent on your harvest took work. Inspired by Bob Dylan’s comments on the subject at Live Aid, Nelson, along with John Mellencamp and Neil Young, founded Farm Aid, an annual benefit concert to raise funds to help farmers stay afloat.


The shows featured several artists spanning many genres, with Nelson performing at every edition since its inception.

Willie’s Reserve

Over the years, Nelson has been a part of many business ventures, including restaurants, truckstops, BioDiesel, television, books, movies, a SiriusXM channel, commercials with Martha Stewart and Snoop Dogg, etc. However, one successful venture was more than a natural fit.

It’s no secret that Nelson enjoys his weed. Many artists have tales of getting high on Willie’s bus, and his consumption of the sweet leaf is the stuff of legend, leaving others in the dust.


In 2015, that love and appreciation became a business with Willie’s Reserve coming to market. The company offers several different products produced by local growers in keeping with Farm Aid’s philosophy of supporting American farmers. Nelson also appointed himself as Chief Tester, to which I say no one is more qualified!


At 90 years old, Nelson shows no real signs of slowing down. Dates are already starting to line up in 2024, and we can certainly expect new releases to come down the line. The highlights mentioned above are a mere fraction of the many that have marked his life and career, with more sure to come if he continues at this pace.

Willie could retire tomorrow and leave a legacy that most artists can only dream of having even a fraction of. Let’s hope for many more years of music from the Red-Headed Stranger; we'll keep listening if he keeps playing them.

By Kevin Daoust - instagram.com/kevindaoust.gtr

Kevin Daoust is a guitarist, guitar educator and writer based in Gatineau, Quebec, Canada. When not tracking guitars for artists around the world, or writing music-related articles around the internet, he can be seen on stage with Accordion-Funk legends Hey, Wow, the acoustic duo Chanté et Kev, as well as a hired gun guitarist around Quebec and Ontario. He holds a Bachelor of Music in Guitar Performance from Carleton University in Ottawa, Ontario, Canada.



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