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Willie Nelson Songs: 15 of the Outlaw Country Icon’s Hits, Ranked & the Stories Behind Them

Plus, get all the details on the nonagenarian's newest book!

When it comes to country music, there’s no one quite like Willie Nelson. Over the course of an astonishing career that’s lasted more than 60 years, he’s written and performed some of the most enduring songs in the genre, and carved out his signature rebellious yet easygoing persona. Willie Nelson began writing songs in the mid-’50s, and released his debut album in 1962. By the ’70s, he was a megastar and one of the kings of “outlaw country,” the rebellious sub-genre of country music also associated with artists like Waylon Jennings, Johnny Cash and Kris Kristofferson.

During his long career, Willie Nelson has become a full-fledged icon equally beloved by country folks, rockers and hippies, and he’s finally being inducted into the Rock & Roll Hall of Fame on November 3. His fanbase spans generations, and his career isn’t limited to music — he’s also an actor, activist and writer.

MUST-READ: Willie Nelson Young: Must-See Photos of the Country Icon Before the Braids

Cover of 'Energy Follows Thought' by Willie Nelson

Nelson’s just-released book, Energy Follows Thought: The Stories Behind My Songs, offers an inside look at his creative process, complete with never-before-seen pictures, handwritten lyrics and anecdotes about the many musical legends he’s collaborated with.

At 90 years young, Nelson has seemingly endless stories to share. In honor of his new book, we’re taking a look back at some of the greatest Willie Nelson songs, in his own inimitable words.

15 greatest Willie Nelson songs, ranked

We dove deep into the vaults to find some of the most amazing Nelson songs in his extensive songbook. Do you agree with our ranking?

15. “Little Old Fashioned Karma” (1983)

The concept of karma has inspired musicians from John Lennon to Taylor Swift, and Nelson offered his own take on it in 1983, with a track sparked by his grandma.

Following his grandpa’s death when he was a kid, Nelson and his family struggled, but as he recalls in Energy Follows Thought, “Then karma kicked in. Good old-fashioned karma. Mama Nelson had spread such goodwill throughout her life that goodwill came smiling back her way,” leading her to get a job that allowed her to provide for her family.

14. “Good Hearted Woman” (1976)

“Good Hearted Woman” is a collaboration between Nelson and another icon of outlaw country, Waylon Jennings. The song came to be during a rowdy night of poker. Jennings was almost done writing it, but felt there was a missing piece. Nelson suggested the line “Through teardrops and laughter we’re gonna walk through the world hand in hand,” and Jennings loved it so much that he gave Nelson half the credit for the song.

13. “Bloody Mary Morning” (1974)

“Bloody Mary Morning” is a song about how “Fright leads to flight,” writes Nelson. Following a breakup, he gets on a plane and leaves his troubles behind — for now, at least. As he wryly observes of the song, “Good to be flying thirty-three thousand feet above the ground. Good to be suspended in air. Suspended in time. Good to feel the effects of spicy tomato juice and hundred-proof Smirnoff.”

12. “Half a Man” (1963)

Nelson wrote “Half a Man” on his honeymoon — but don’t be fooled, this isn’t your typical love song! As Nelson recalled, “[My wife] was sleeping on my right arm. I wanted to smoke and, not wanting to disturb her, reached around with my left arm to grab a cigarette off the nightstand. Suddenly the thought came to me, ‘If I’d only had one arm to hold you . . .'” and so one of his quirkiest early tracks was born.

11. “I Am the Forest” (1983)

Nelson is one of country music’s great philosophers. In this song, he drew from 19th-century transcendentalist writer Henry David Thoreau to create a stunning image of our connection to the natural world. As Nelson explains the guiding force for the song, “You, me, the trees, the bees, the bears, the waterfalls, the rocks and stones and even the Spanish rose that grows in Harlem are all connected… if you are me and I am you and we are all one thing, everything is everything and everything is just fine.”

10. “Me and Paul” (1971)

“Me and Paul” is a tribute to Nelson’s longtime drummer, Paul English. Nelson and English met in the ’50s and became musical collaborators and close friends for decades. Nelson says the song is about “the wandering ways of imperfect men.” Over the course of more than 60 years together, “Paul’s loyalty never wavered — not once,” writes Nelson. Sadly, Paul passed away in 2020, but the song lives on.

9. “Funny How Time Slips Away” (1962)

The passing of time is always a rich subject for country songwriters, and this Willie Nelson song has only become more potent in the 60-plus years since he wrote it (the song was even covered by Elvis in 1971!). Nelson found inspiration from noir movies he loved, like Kiss Me Deadly and The Big Heat and called the song “a mini movie, with its black widow–type character, a woman who does a man dirty.”

8. “Why Do I Have to Choose” (1983)

Nelson calls “Why Do I Have to Choose” “a song about romantic bewilderment” — and he makes this bewilderment sound darn good! The song centers on a man choosing between two women, and fellow country icon and Nelson collaborator Merle Haggard praised it for “start[ing] out sweet and then go[ing] sour.”

7. “Shotgun Willie” (1973)

You gotta love Nelson’s sense of humor! “Shotgun Willie” opens with the line “Shotgun Willie sits around in his underwear.” As he recalled, his record label had tasked him with writing a new set of songs and “Because something new didn’t come to mind, I just looked in the mirror and wrote about what I saw: me in my underwear” — and against all odds, it worked. As Nelson put it, “I figured it was a funny image, and besides, it put me in a reflective mood.”

6. “Hello Walls” (1962)

“Hello Walls” may have been a big hit for singer Faron Young but the clever lyrics are classic Nelson. In the song, a lonely man starts talking to the walls — an image that came to Nelson while sitting in his Nashville office during his earliest days as a professional songwriter. “I stared at the walls and the walls talked back,” he remembered. “So did the ceiling. So did the window. I scribbled down whatever was coming through me, whether it made sense or not.”

5. “Forgiving You Was Easy” (1985)

Nelson described this poignant breakup song as “a young man’s song written by middle-aged me.” When writing it, Willie Nelson knew it was one of those songs would resonate with a variety of listeners and become a hit. “I think I’m able to channel the feelings of the common man and common woman because I’m a common man,” he says. “I don’t try to second-guess feelings. I just try to let feelings flow through me. And I’m sure my feelings — especially those about love and loss — are about the same as most people’s.”

4. “Crazy” (1962)

Nelson wrote “Crazy” early in his career, and the song became a signature hit for Patsy Cline. As an up-and-coming musician, Nelson faced self-doubt, but “Crazy” helped him find confidence (and financial success — he quipped, “Because Patsy liked it, I was poor no longer”). As he describes, “Crazy is as crazy does, and this particular ‘Crazy’ convinced me, at a time when I wasn’t a hundred percent sure of my writing talent, that I’d be crazy to stop writing.”

3. “Angel Flying Too Close to the Ground” (1981)

This “sorrowful song,” as Nelson describes it, is all about a woman who’s too good for the man who loves her. Nelson sees the song’s poignant story as having a universal appeal. “I can’t tell you how many people have asked me to name the angel I have in mind,” he writes. “My answer is always the same: ‘It could be any one of a thousand angels. You name her. You tell me who she is.'”

2. “Blue Eyes Crying in the Rain” (1975)

Nelson may not have written “Blue Eyes Crying in the Rain,” but his version of the classic ’40s country song became one of his biggest hits and helped reinvigorate his career after years of ups and downs. The sadness of the song spoke to Nelson. “It can feel good to feel bad — at least in songs,” he says. He first heard it when he was 14, and it always stuck with him. “The sadness inherent in that song is timeless,” he writes. “I’d also call the sadness beautiful because it’s so sincere.”

1. “On the Road Again” (1980)

In a tie for first place for best Willie Nelson songs, was “You Were Always on My Mind” (1972), but ultimately “On the Road Again” won out. It’s one of the most iconic examples of Nelson’s mellow, good-natured spirit. He originally wrote the song for the soundtrack of a movie he was starring in, Honeysuckle Rose, but it quickly took on a life of its own, topping the charts and winning a Grammy. Nelson said, “Without knowing or trying, in a few little lines I’d written the story of my life.”

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