Willie Nelson’s career has spanned seven decades, producing some of the most iconic and revolutionary music in the country genre. Nelson also personifies the sub-genre known as outlaw country—a musical movement that stands not just for life in rural America, but for the rebellious spirit that comes with it. Nelson is known for his activism, rejection of authority, and advocacy for marijuana legalization—all of which play a role in his “outlaw” persona.
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But the truth is that that persona is intensely real. Nelson is a natural rebel, and his music has always shown it. These six songs are just a few that define his adventurous spirit in perfect outlaw style.
1. “Me and Paul” (1971)
Nelson recorded “Me and Paul” back in 1971, but didn’t release it until it appeared as the title track of an album released in 1985. The song was an homage to his friendship with drummer Paul English, who Nelson worked with for the duration of their careers. “Me and Paul” describes wild life on the road—getting into scrapes, making memories, and getting into more than one tussle with the law. English passed away in 2020 at the age of 87, but he lives on in country music history as the outlaw sidekick who supported the great Willie Nelson both on and off stage across a life full of adventure.
2. “Whiskey River” (1973)
“Whiskey River,” a mournful song about drowning one’s sorrows, has become a staple of Nelson’s expansive catalog. But the Red Headed Stranger didn’t write the song; it was written by Johnny Bush and Paul Stroud, and originally released by Bush. Bush’s version was a hit, but it was Nelson’s reworking of the tune that went down in history.
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Maybe it was his gritty vocals, his surprisingly delicate guitar playing, or the way he incorporated elements of blues and jazz. Whatever it was, Nelson’s “Whiskey River” captures all the darkness of drowning in booze after having one’s heart broken. He performed it on the first-ever episode of Austin City Limits, further cementing its legacy in outlaw country music.
3. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” (1978)
When two country music legends like Willie Nelson and Waylon Jennings team up, they are bound to conjure up something amazing. The duo released three full albums together, with “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” appearing on the first, which was simply titled Waylon & Willie. They might not have written the song—it was first recorded by country singer Ed Bruce—but their version is by far the most famous. Their adaptation features electric guitars, providing a powerful backing to a mournful song about the loneliness and waywardness of being a cowboy. Their grizzled vocals represented a warning about the very lifestyle they themselves led. The song earned the duo a Grammy Award.
4. “Highwayman” (1984)
In the 1980s and ’90s, Nelson was part of the supergroup The Highwaymen, which was loaded with classic country star power: Nelson and Jennings were joined by Johnny Cash and Kris Kristofferson in the project. The Jimmy Webb-penned song they named themselves after was a massive hit, earning the group a Grammy Award for Best Country Song.
“Highwayman” follows four stories of so-called highwaymen through the ages, from an ancient sailor to a futuristic interstellar voyager. Each verse ends with the death of the highwayman, but stipulates that his death was not the end of his story. Nelson’s opening verse follows a roadside bandit who was hanged for his crimes.
5. “Bloody Mary Morning” (1974)
The early 1970s were a difficult time for Nelson. After his second divorce, he considered leaving music briefly but rallied to record Phases and Stages. This concept album following a couple’s divorce featured the track “Bloody Mary Morning,” a song that feels both heartbroken and lively. It’s about starting an aimless journey fueled by alcohol after waking to find that your lover has left you. “Bloody Mary Morning” marked a comeback for Nelson, as it peaked at No. 17 on the country charts and became one of his standards.
6. “On the Road Again” (1980)
Even those who aren’t fans of Willie Nelson know “On the Road Again.” The song has become his signature tune, encapsulating all there is to know about the singer’s restless spirit and love of adventure. It was written for his album Honeysuckle Rose, and lovingly describes life on tour. It’s a cheerful ode to the freedom and excitement life as a musician can offer. “On the Road Again” earned Nelson another Grammy Award and was inducted into the Grammy Hall of Fame in 2011. The song will forever stand out for best representing the outlaw country soul that Nelson embodies.
Photo by Rob Verhorst/Redferns
