With more than six decades of making music, and more than 100 albums released during that time, it’s not easy paring down to Willie Nelson’s most essential tracks. And no discussion of the country legend’s career is complete without a survey of his best, and often genre-bending albums, including 1975’s career-boosting Red Headed Stranger and the 1978 American Songbook milestone Stardust.
But as you’ll see in the below list of the Top 10 Willie Nelson Songs, while his first genre of choice was country music, the Texas-born singer-songwriter has taken a restless path since his debut recording appeared in 1957, crossing over to pop, adult contemporary and standards. He was even at the forefront of the 1970s outlaw country movement, which gave country music a tougher, rock-inspired edge.
His songs have been covered in almost every category that can be named: blues, soul, jazz, gospel and hard rock. The below list can’t begin to cover the scope of his influence and legend, but these 10 songs are a good place to start.
10. “Night Life” (1960)
One of Nelson’s earliest songs has a tangled history – including the broke songwriter selling his composition and recording under a pseudonym – before country star Ray Price had a hit with it. It’s since become one of Nelson’s most covered songs and the start of a songwriting career that kept him busy until his solo records took off in the ’70s. Its bluesy chorus became his mantra: “The night life ain’t no good life, but it’s my life.”
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9. “Stardust” (1978)
In the middle of his peak outlaw country period, Nelson threw a curve to his record company and fans by making an album of standards from the ’20s through the ’50s. Stardust went on to become his biggest-selling LP. Among its 10 covers are American Songbook favorites by Irving Berlin, the Gershwins and Hoagy Carmichael, who cowrote the 1927 lovelorn classic that leads the album and gives the LP its name.
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8. “Angel Flying Too Close to the Ground” (1980)
“Angel Flying Too Close to the Ground” is so revered by other luminary songwriters that even Bob Dylan has covered it. The song was first released on the soundtrack to Nelson’s 1980 movie Honeysuckle Rose, his first starring role after a breakout performance in the previous year’s The Electric Horseman. As the album’s second single (after the signature “On the Road Again”), it became his seventh country No. 1.
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7. “Me and Paul” (1971)
Before Red Headed Stranger made Willie Nelson a star, he released another concept album: 1971’s Yesterday’s Wine is one of country music’s first conceptual records, a semiautobiographical story about the “Imperfect Man.” The wholly autobiographical “Me and Paul” details the relationship between Nelson and drummer Paul English, who played with Nelson since 1955: “We received our education in the cities of the nation.”
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6. “Whiskey River” (1978)
Willie Nelson’s songwriting resume runs long and deep, having penned hits for Patsy Cline (“Crazy”) and Roy Orbison (“Pretty Paper”) before becoming a solo star in the ’70s. But his interpretative skills over the years have resulted in definitive versions of songs written by others. Johnny Bush’s “Whiskey River,” first recorded by Nelson in 1973 but perfected live in 1978, is one of the best. A show opener since the mid-’70s.
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5. “Pancho and Lefty” (1983)
Several of the 100-plus albums Nelson has released since the early ’60s have been collaborations with friends. A handful of these have been with fellow country legend Merle Haggard. Their first album together, Pancho & Lefty, includes the definitive version of Townes Van Zandt’s tale of a pair of bandits on the run. Their sympathetic reading spotlights two of the genre’s greatest singers at their interpretative best.
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4. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” (1978)
Ed Bruce had a Top 15 country hit with his “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” in 1975, but it’s Nelson’s take, alongside fellow outlaw country pioneer Waylon Jennings, from three years later that everyone knows. Their version went to No.1. Its parent album, Waylon & Willie, was the first Nelson album to crack the pop Top 25, making its way to No. 12. Within four years, he’d have his first Top 10.
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3. “On the Road Again” (1980)
After being cast as the lead in the 1980 movie Honeysuckle Rose, about a touring artist not unlike Nelson himself, the road-toughened singer was asked to write a song to fit the film’s theme. He quickly scribbled “On the Road Again” on an air sickness bag while in flight; the track soon became one of his signature songs. It was another country No. 1 for Nelson, who also scored his biggest pop hit at the time. A key cut in his timeline.
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2. “Always on My Mind” (1982)
Nelson’s 27th album mixes songs by Simon & Garfunkel (“Bridge Over Troubled Water”) and Procol Harum (“A Whiter Shade of Pale”) with some new originals. Its highlight, though, is a cover of a decade-old song previously recorded by Brenda Lee and Elvis Presley: “Always on My Mind” became Nelson’s only Top 10 solo hit and the exemplary version of an oft-sung weeper. He’s at his heartbreaking best here.
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1. “Blue Eyes Crying in the Rain” (1975)
Predecessors Shotgun Willie and Phases and Stages finally brought Nelson some country chart success, but Red Headed Stranger, his 18th album, is the one that made him a star. A No. 1 country hit and Nelson’s first Top 40 showing, the conceptual piece weaves original songs with choice covers, including Fred Rose’s mid-’40s “Blue Eyes Crying the Rain.” Nelson claims the song as his own, forever altering his history.
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