Willie Nelson: A life in 90 songs

As long as there’s been country music, there’s been Willie Nelson. That might not be historically accurate, but it damn may as well be. For more than seven decades, no one has been able to embody all of the genre’s contradictions, facets, and elements quite like Nelson. A troubadour in every sense of the word, Nelson was able to turn the various twists and turns in his life into a tapestry of songs that still resonate as the man himself enters his 90th year.

Hailing from Abbott, Texas, Nelson first got into the music business not as a singer or songwriter but as a record DJ. His experiences would help shape early songs like ‘Mr. Record Man’, and by the end of the 1950s, Nelson had sold enough songs that he decided to move to Nashville, Tennessee. On the strength of his songwriting ability, Nelson was signed to Liberty Records and then RCA while he invested his royalties into his own career.

Unable to fit into the clean-cut Nashville system, Nelson retired from the industry in the early 1970s and moved to Austin, Texas. It was there that Nelson stumbled upon the burgeoning hippie scene blossoming out of the city. Now inspired to grow his hair and sing about more risque subjects, Nelson reinvented himself as one of the first true outlaw country superstars. Albums like Shotgun Willie and Red-Headed Stranger established his uniquely fragile vocal tone along with the singular guitar tone produced by his nylon acoustic guitar lovingly nicknamed ‘Trigger’.

By the 1980s, Nelson had become one of the most successful country music artists of all time. He reinvented himself with an album of jazz standards, Stardust, and began leaning more heavily on cover material. He also joined the supergroup The Highwaymen along with fellow outlaw country icons Waylon Jennings, Kris Kristofferson, and Johnny Cash. His commitment to supporting American agriculture also led Nelson to found the benefit concert series Farm Aid along with John Mellencamp and Neil Young.

Even though his first recording was released more than 60 years ago, Nelson continues to be active as a musician, author, and activist. As politically conscious and pop-culturally relevant as he’s ever been, Nelson remains a figurehead for cannabis advocacy, left-wing politics, and outlaw country as a genre. In fact, Nelson is arguably still the face of country music as a whole, all thanks to his unmatched body of work that stretches back to the 1950s.

Here are 90 of Willie Nelson’s best songs, one for each year of his remarkable life.

Willie Nelson’s 90 best songs:

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