Willie Nelson: The Last Outlaw

The 21st century has proven to be an unforgiving time for our country heroes. Waylon Jennings passed away in 2002, Johnny Cash left us in 2003, and Merle Haggard in 2016. In 2011, Hank Williams Jr. lost all his bona fides, and with the recent passing of Kris Kristofferson in September 2024, we’re reminded that the true original outlaws of country music are nearly all gone. All except for one: Willie Nelson, the last outlaw.

His newest record, released in November 2024, is cleverly titled The Last Leaf on the Tree and was produced and arranged by his son Micah Nelson. It is his 153rd album to date. Primarily a cover album, it is reminiscent of the cover album Johnny Cash recorded with Rick Rubin just before his death. The record features just two tracks written by the famed outlaw, while the rest are covers of songs by Tom Waits, Neil Young, Beck, Keith Richards, The Flaming Lips, and more.

Willie started playing music at the age of seven and joined his first band at ten years old. In high school, he was the singer and guitarist of a polka band, but it was after a short stint in the U.S. Air Force that he buckled down and started to come into his own.

While working as a radio disc jockey in the 1950s, he wrote some of country music’s standard tunes and quickly made a name for himself as a songwriter. In the 1960s, Nelson moved to Nashville, Tennessee, wrote and recorded his first record, and joined the Grand Ole Opry. Songs like “Crazy” and “Funny How Time Slips Away” were covered by legends such as Patsy Cline and Elvis Presley and will forever stand the test of time.

The 1970s were a time of change in country music. This was when Willie Nelson made his move to Austin, Texas, staked his claim, and earned his outlaw country crown. The albums Shotgun Willie, Red Headed Stranger, Stardust, and Yesterday’s Wine were all released in the early ’70s and catapulted Nelson to legend status. In 1975, he joined fellow outlaw Waylon Jennings to write and record Wanted! The Outlaws.

“Mamas Don’t Let Your Babies Grow Up to Be Cowboys,” “Good Hearted Woman,” and “If You’ve Got the Money I’ve Got the Time” were all released in the 1970s and set the tone for what would come from the ambitious songwriter.

While the 1980s brought bad fashion and tacky electronic music to the forefront, Willie Nelson seemed unfazed by the landscape and continued to take the road less traveled. In 1981, he was hospitalized for a collapsed lung. After several pneumonia scares, he decided to quit smoking—cigarettes or marijuana. I think we all know which one he chose.

This decade was full of milestones for the songwriter and proved to be another successful era for Shotgun Willie. Songs like “On the Road Again” and “Pancho and Lefty” became iconic in the music world. In the mid-1980s, he joined a supergroup called The Highwaymen with Johnny Cash, Waylon Jennings, and Kris Kristofferson. Nelson also helped organize the famous music festival Farm Aid in 1985 and has performed at the event every year since.

The 1990s brought IRS and tax troubles for the veteran songwriter, prompting him to record a double album titled The IRS Tapes: Who Will Buy My Memories? The profits from the record, along with an auction of all his assets, cleared Nelson’s debt with the Revenue Service. In 1993, he was inducted into the Country Music Hall of Fame. During the IRS scandal, Nelson feared his famous Martin guitar, “Trigger,” might be auctioned off. He was quoted as saying, “When Trigger goes, I’ll quit.” Luckily, that never happened, and his guitar is as much a troubadour as Willie himself.

Photograph by Wyatt McSpadden

Since the turn of the century, Nelson has continued to write and record a new album almost every year while touring extensively. He has also had cameos in several films and TV shows throughout his career and has written several books about his life. In 2012, he even shared the spotlight with rapper Snoop Dogg and recorded the song “Roll Me Up and Smoke Me When I Die.” Even though the song is extremely cheesy and features a subpar singing performance from Snoop, it’s still a catchy lyric and quickly became an anthem among fans of both artists.

To me, Willie Nelson has always stood for freedom: freedom to go against the grain and carve your own way into the life you could only dream of. In an interview with Rolling Stone magazine, he laid out the three rules of the Nelson family: Don’t Be an Asshole, Don’t Be an Asshole, and Don’t Be a Goddamn Asshole. We could all take a page from his book on how to follow your dreams and what it means to be successful in life.

Throughout his lifelong journey, he has taken a beating from women, the music industry, and all the perils life could throw his way. Yet, he overcame the oppression of the mainstream, and even in his golden years, he still seems to turn water into wine. Yesterday’s wine.

Willie Nelson was born April 29, 1933, and in 2025, he is still touring and playing shows almost every night. He’s 91 years old, and sadly, it’s starting to show.

Let’s hope that Ol’ Shotgun Willie stays around a little while longer to tell stories and sing the lullabies of the old outlaw ways.