Recommendations of the Editorial team
When Willie Nelson released his tribute album to the Gershwin brothers in 2016, he showed his reverence for the Great American Songbook. In fact, Nelson’s own work also deserves an album or two. The native Texan has written some of the most important titles in music history. From “Crazy”, made famous by Patsy Cline, to “Funny How Times Slips Away”, covered by Elvis Presley.
And then there are the songs that have become his trademark thanks to his charmingly eccentric voice. It is impossible to hear a Willie Nelson performance and not identify him as such.
Whether he was singing Countrypolitan songs in the ’60s – his 1962 debut album “…And Then I Wrote” is notable for its wealth of timeless songs – or breaking new ground with Waylon Jennings in the ’70s, Nelson always turned heads with his distinctive voice.
Country music rebel
“Suddenly we were outlaws,” Nelson told Rolling Stone in 2014, reflecting on the country music rebellion he was credited with pioneering. “I thought it was incredibly funny. And I tried not to disappoint her!”
“Angel Flying Too Close to the Ground” (1981)
Nelson played a version of himself in 1980’s “Honeysuckle Rose,” a musical drama about an unsuccessful country singer that was elevated above guilty pleasure status by its live concert-inspired soundtrack. Co-stars Amy Irving and Dyan Cannon, as well as Emmylou Harris, Hank Cochran, Jeannie Seely and fiddler Johnny Gimble joined Nelson and his Family Band on the LP, which included songs such as “Pick Up the Tempo” and “Heaven and Hell.”
The road anthem “On the Road Again” became a ubiquitous classic. But it’s the heartbreaking “Angel Flying Too Close to the Ground” that deserves to be considered an American standard. Later covered by Bob Dylan and Alison Krauss, it is a bittersweet reflection on deep love and even deeper loss. Featuring a no-frills production and one of Nelson’s most vulnerable and captivating vocal performances ever.
“Crazy” (1962)
Nelson had originally hoped that Grand Ole Opry member Bill Walker would record “Crazy.” But Walker thought the song was too feminine. So Nelson offered it to Patsy Cline, whose 1961 recording of “Crazy” became one of the defining ballads of the 20th century.
A year later, Nelson released his own version, singing the song with a voice unaffected by age or marijuana use. It is one of the earliest examples of his unique, unpredictable phrasing, with each word landing somewhere before or after the actual beat.
Cline took a different approach, smoothing out the inaccuracies she heard in Nelson’s demo in favor of smooth, controlled vocals. For a song about heartbreak, however, Nelson’s rendition is perhaps the more effective, delivered with the faltering uncertainty of someone coming to terms with their own madness.
“On the Road Again” (1980)
There’s something charmingly crude about the fact that Nelson wrote one of his biggest and best-known hits on the back of a doggy bag. “On the Road Again” was written spontaneously during a flight as the theme song for Honeysuckle Rosethe 1980 film about an outlaw country singer who doesn’t quite make it to the top, starring Nelson himself.
The film may have been an alternative reality to his own life. But the song was typical of real life. A cheerful, stirring travelogue that was perfect for award shows and commercials. That fits well. Because no song celebrates Nelson’s love of life on the road and making music with his friends more easily than this one.
“Night Life” (1965)
It’s no coincidence that guitar heroes like BB King and Thin Lizzy tried their hand at “Night Life.” A tribute to the early hours of the morning, the song fires on both cylinders with sad stories and six-string riffs, creating an alternating vocal between Nelson’s nighttime observations (“Listen to the blues they’re playing!”) and the guitar parts that follow.
The riffs in the middle of the song were written by Paul Buskirk, who bought the song for $150 from the perpetually cash-strapped Nelson and played on the original recording in 1960. Still, Nelson was the song’s primary architect. And rarely before had he built such a solid bridge between his singing and his guitar playing.
“Me and Paul” (1971)
Bro-country may have emerged decades after the release of “Me and Paul” in 1971. But even then, Nelson was singing his own kind of bro anthem. The song is dedicated to his drummer Paul English. “Me and Paul” is a road chugger about the pitfalls of touring life, the dangers of Music Row and how everything is better with a partner in crime.
The song first appeared on Yesterday’s Wine and then as the title track of the album Me & Paul from 1985. It is the counterpart to the highway glory of “On the Road Again” and deals with the mischief and dangers that lurk from stop to stop. “I think Nashville was the hardest,” he sings over a classic honky-tonk stomp, predicting his own future.
Nelson almost gave up music altogether after “Yesterday’s Wine” was not a success. But the fact that he defiantly revived “Me and Paul” shows that in the end, only his own opinion mattered.