Home Music Music Country Lists

Willie Nelson: 20 Essential Songs

From the signature ballad he wrote for Patsy Cline to his love letter to life on the road

When Willie Nelson released his 2016 tribute album to the Gershwin brothers, he was showing his reverence for the Great American Songbook. But the fact is that Nelson’s own works deserve a volume or two. The Texas native has written some of music’s most important titles, from “Crazy,” made famous by Patsy Cline, to “Funny How Times Slips Away,” covered by Elvis Presley.

And then there are the songs with which he has become synonymous, thanks to his charmingly eccentric vocal delivery. It’s impossible to hear a Willie Nelson performance and not identify it as such. Whether he was crooning Countrypolitan fare in the Sixties – his 1962 debut album …And Then I Wrote is remarkable for its wealth of enduring songs – or busting down doors with Waylon Jennings in the Seventies, Nelson was always making waves with that unmistakable voice.

“All of a sudden, we were outlaws,” Nelson told Rolling Stone in 2014, reflecting on the country music rebellion he was credited with launching. “I thought it was the funniest thing in the world. And I tried not to disappoint ’em!”

Play video

David Redfern/Redferns

“Bloody Mary Morning” (1974)

The bleary-eyed hangover of “Bloody Mary Morning” was the morning-after moment of clarity that Nelson needed at a pivotal time in his career. His marriage in shambles, his contract with RCA Records going nowhere, and all signs pointing him back to Texas, the song’s autobiographical statement of purpose didn’t really register when it first appeared on 1970’s Both Sides Now. But Nelson didn’t give up on it, and when he played it at a party two years later it caught the ear of Atlantic’s Jerry Wexler. The rest, as they say, was history. Reworked for his breakthrough concept album, Phases and Stages, the song’s goose-chasing banjo gave the soon-to-be Red Headed Stranger a crucial hit and helped establish the footloose spirit that’s been at the core of his work ever since.

Play video

David Redfern/Redferns

“Mammas Don’t Let Your Babies Grow Up to Be Cowboys” (1979)

For all the hit songs that Nelson wrote for other people over the years, it’s hard to think of a song written by someone else that could be as perfectly suited for him as “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.” The song had already charted with its author, Ed Bruce, and been covered by Chris LeDoux before Nelson and Waylon Jennings tackled it on 1978’s Waylon & Willie – but all other versions were relegated to footnotes once they’d touched it. (Even the Chipmunks’, whose parody was inspired by Nelson and Jennings’ definitive reading.) The Lone Star belt buckles and smoky old pool rooms fit in perfectly with the outlaw country mystique, but it’s the delivery that sells it: You get the feeling that Jennings is that dark, distant cowboy, but Nelson’s warm, airy contrast gives the song the wry, knowing wink that it needs.

Play video

David Redfern/Redferns

“Forgiving You Was Easy” (1985)

Nelson has always been a master at meditating on memory, and the capability of our brains to know when to move on and when to linger. “Forgiving You Was Easy,” from 1985’s Me & Paul, finds Nelson applying this insight to the nuances of relationships, and how complex our hearts can be when scorned by the one we love. “I could probably apply it to a dozen situations in my life,” Nelson has said about the tender, Tejano-tinged ballad that went to Number One in 1985 – on the same day, in fact, that Live Aid aired worldwide and raised millions for the famine across Africa. The synchronicity birthed his own idea: Farm Aid, which held its first concert that September in Chicago. Naturally, Nelson played “Forgiving You Was Easy” during his set, and he hasn’t forgotten the farmers ever since.  

Play video

David Redfern/Redferns

“Whiskey River” (1973)

This iconic Nelson tune, which has doubled as his concert-opening song since time immemorial, was actually written by Johnny Bush. Nelson cut it for his 1973 album Shotgun Willie, empowering it with a grooving bass line and giant vocal harmonies over which he languidly laments a high-proof river he hopes never runs dry. But the more faster flowing “Whiskey River” wasn’t released as a single until 1978, when Nelson included it on that year’s live album Willie and Family Live, where it seamlessly segued into “Stay a Little Longer.” Since then, it’s been synonymous with Nelson, who once even hawked his own Old Whiskey River bourbon.

Play video

David Redfern/Redferns

“Good Hearted Woman” (1976)

Nelson and Jennings, two good-timing men if there ever were, had perfect timing when they dropped this duet in 1976. The “duet” was a bit of an illusion, however, as Jennings had already released the song in 1972, but overdubbing Nelson’s vocals and some fake crowd noise gave “Good Hearted Woman” some extra pep, and it was added to Wanted: The Outlaws! The song dated back seven years to when Jennings came up with it over a poker game, inspired by an ad for Ike & Tina Turner, with Nelson’s then-wife Connie Koepke writing down the lyrics as they played. (The Turners, ironically, split up for good after a fight in Dallas in ’76.) The new version went on to top the country charts and crack Billboard’s Top 40, while Wanted became country’s first platinum album – pushing Waylon and Willie and the boys once and for all into the mainstream.

Play video

David Redfern/Redferns

“Family Bible” (1971)

Nelson originally wrote this song early in his career, selling the track to be recorded by Texas country artist Claude Gray, who counted the song as his biggest hit. Years later, Nelson included his own version of the song on the 1971 album Yesterday’s Wine, a commercially unsuccessful concept album that follows one man’s journey from birth to death. The song’s lyrics, which celebrate the Southern tradition of maintaining a family Bible, were inspired by Nelson’s own grandmother. “Family Bible” was never a big hit for Nelson but remained close to his heart, becoming a concert mainstay and inspiring a 1980 gospel album of the same name. His performance of the song, opposite Johnny Cash during a 1998 VH1 Storytellers, is particularly moving, but never preachy. 

Play video

David Redfern/Redferns

“Hello Walls” (1962)

Willie Nelson was so broke in 1961 that he offered to sell “Hello Walls” to Faron Young for $500. Young had already recorded the song, though, and “Hello Walls” – a tragicomedy about a man who’s so lonely that he speaks to his own bedroom – was on its way to becoming a hit. Knowing a big payday was on the horizon, Young loaned him the $500 instead, allowing Nelson to keep the publishing rights. Less than two months later, while “Hello Walls” was enjoying a nine-week run at Number One, Nelson received a $20,000 royalty check. Elated, he headed to Faron’s favorite honky-tonk to express his thanks with some surprise PDA. “I was sitting at Tootsie’s,” Young recalls in the biography Live Fast, Love Hard: The Faron Young Story, “and this big hairy arm came around my neck, and Willie french-kissed me. . .It’s probably the best kiss I ever had.”

Play video

David Redfern/Redferns

“Always on My Mind” (1982)

Willie Nelson first heard “Always on My Mind” during the recording sessions for Pancho & Lefty, when studio guitarist Johnny Christopher – one of the song’s three co-writers – pitched it to Merle Haggard. When Haggard passed on the tune, Nelson quickly claimed it, re-entering the studio as soon as Pancho & Lefty was done to track another solo album. “Always on My Mind” became the record’s titular tune, dressed up with sweeping strings and swelling brass by producer Chips Moman. Elvis Presley’s 1972 recording may have popularized the song, but it was Nelson’s version – sung in a warbling, guilty-as-charged voice that cuts through Moman’s thick arrangement – that won three Grammys. 

Play video

David Redfern/Redferns

“Pancho and Lefty” (1983)

Townes Van Zandt’s tale of Mexican banditry, brotherhood and betrayal was more than a decade old when Willie Nelson and Merle Haggard cut their own version in 1983, turning the song into a duet. Their timing couldn’t have been better. Outlaw country still ruled the roost, and “Pancho and Lefty” was the ultimate outlaw tale, positioning its two characters as sympathetic anti-heroes who were loved by mothers and hated by federales. Nelson sent a staggering 16 albums into the Top 10 during the 1980s, but none left as deep an impression as Pancho & Lefty, whose title track proved that the 50 year-old singer could shoot as straight as the younger guns.  

Play video

David Redfern/Redferns

“Pretty Paper” (1964)

Originally a hit for Roy Orbison in 1963, “Pretty Paper” was inspired by a vendor outside a department store in Fort Worth, Texas. An amputee with no legs who peddled paper and pencils for a living, Nelson suddenly recalled the man a few months before Christmas, and put the memory to music. “He had a way of crying out those words – ‘Pretty paper! Pretty paper! – that broke my heart,” Nelson wrote in his autobiography It’s a Long Story. Nelson recorded the song himself, produced by Chet Atkins, in 1964, and then again as the title track for his 1979 Christmas album. Stripped of the Orbison sheen, Nelson made it a sweet and simple Southern waltz, anchored by some of his most aching, pristine vocals: his tender vibrato as he sings the word “ribbons” is enough to warm even the most calloused of holiday hearts. 

Play video

David Redfern/Redferns

“Funny How Time Slips Away” (1962)

One of Nelson’s earliest songs, “Funny How Time Slips Away” was written during the same week as “Crazy” and “Night Life.” Nearly a half-dozen artists have turned the song into a Top 40 hit since then, including soul artist Joe Hinton, rockabilly singer Narvel Felts and teen idol Jimmy Elledge. Even so, Nelson’s own delivery always packed the biggest punch, with lines like “It’s been so long. . .but it seems now that it was only yesterday” taking on new meaning as Nelson grew older, outliving close friends like Merle Haggard and Waylon Jennings along the way. Originally a ballad about a short-lived relationship, it’s grown into something bigger: a textbook example of the sort of ageless songwriting that exists long past its maker.

Show Comments