Willie Nelson: 20 Essential Songs

Nelson played a version of himself in 1980’s Honeysuckle Rose, a musical drama about a struggling country singer that was elevated above guilty pleasure status by its live-concert inspired soundtrack. Co-stars Amy Irving and Dyan Cannon, along with Emmylou Harris, Hank Cochran, Jeannie Seely and fiddler Johnny Gimble, joined Nelson and his Family band on the LP, which included songs like “Pick Up the Tempo” and “Heaven and Hell.” The road anthem “On the Road Again” became the ubiquitous classic, but it’s the artery-slicing “Angel Flying Too Close to the Ground” that deserves to be deemed an American standard. Later covered by both Bob Dylan and Alison Krauss, it’s a bittersweet rumination on deep love and even deeper loss, with uncluttered production and one of Nelson’s most vulnerable, compelling vocal performances of all time.

Nelson had originally hoped Grand Ole Opry member Bill Walker would record “Crazy,” but Walker deemed the song too feminine. So Nelson pitched it to Patsy Cline, whose 1961 recording of “Crazy” became one of the defining ballads of the 20th century. One year later, Nelson released his own version, singing the song in a voice untarnished by age or pot smoke. It’s 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 imprecision she’d heard on Nelson’s demo in favor of steady, controlled vocals. For a song about heartache, though, Nelson’s is perhaps the more effective performance, delivered with the halting hesitancy of someone who’s coming to grips with his own craziness.

There’s something delightfully crude about the fact that Nelson wrote one of his biggest, and signature, hits on the back of a doggie bag. “On the Road Again” was conceived, spur of the moment in the middle of a flight, as the theme song for Honeysuckle Rose, the 1980 film about an outlaw country singer who didn’t quite make it to the top, starring Nelson himself. The film may have been an alternate reality to his own life, but the song was quintessential to the real thing, a jaunty, singalong travelogue tailor-made for awards galas and commercial placements. Which is apt, because no song celebrates Nelson’s band-of-gypsies love affair with life on the road and making music with his friends more simply than this one.

It’s no coincidence that guitar heroes like B.B. King and Thin Lizzy have taken their own stabs at “Night Life.” A salute to the wee small hours, the song fires twin barrels of sad-eyed storytelling and six-string riffage, creating a call-and-response between Nelson’s late-night observations (“Listen to the blues they’re playing!”) and the guitar parts that follow. Credit for those mid-song riffs goes to Paul Buskirk, who bought the song from a perpetually cash-strapped Nelson for $150 and joined him on the original recording in 1960. Even so, Nelson was the song’s main architect, and he’d rarely built such a sturdy bridge between his vocal and instrumental chops before.

Bro-country may have been birthed decades after the release of “Me and Paul” in 1971, but, back then, Nelson was singing his own kind of bro anthem. Dedicated to his drummer Paul English, “Me and Paul” is a road-chugger about the foibles of touring life, the poisons of Music Row and how everything is better with a partner in crime. First appearing on Yesterday’s Wine and then as the title track of 1985’s Me & Paul, it’s a flipside to the highway glory of “On the Road Again,” delving into the mischief and danger that lingers from stop to stop. “I guess Nashville was the roughest,” he sings to a classic honky-tonk stomp and forecasting his own future. Nelson nearly left music altogether after Yesterday’s Wine failed to resonate, but the fact that he defiantly revived “Me and Paul” shows that, ultimately, the only critic that mattered was himself. 

When Nelson recorded his version of this Fred Rose classic in 1975, he hadn’t scored a Top 10 hit in more than a dozen years. His audience was growing smaller. His label was getting worried. An unfazed Nelson responded to all of this concern by releasing a stark, strange concept album, Red Headed Stranger, that topped the country charts even as it flew in the face of the genre’s mid-Seventies trends. “Blue Eyes Crying in the Rain” was the album’s centerpiece: a sad, bare-boned ballad released during an era of string-heavy schmaltz. 

Shooter Jennings once lamented in song that “your heroes turn out to be assholes,” but he could have easily used “cowboys” as a synonym for the coarse slur. While Nelson never overtly equates cowboys with selfish jerks in this bittersweet ballad, it’s easy to read between the lines. Written by songwriter Sharon Vaughn, “My Heroes Have Always Been Cowboys” was cut by Waylon Jennings for Wanted! The Outlaws, but it was Nelson who rode it to Number One with his 1980 version recorded for the Robert Redford movie The Electric Horseman – in which Nelson made his acting debut. The lyrics romanticize “the cowboy ways,” but in the end, the song is really about squandered chances and coming to terms with a life lived without responsibility. “Just take what you need from the ladies and leave them with the words of a sad country song,” Nelson sings. It’s more mournful admonition than boast, and by the time he see his creative prime in the rearview – the result of “picking up hookers, instead of my pen” – you can feel the regret consume him.

This slow-churning shuffle from Nelson’s 1963 sophomore album Here’s Willie Nelson was one of his earliest tracks to earn commercial chart success, peaking at Number 25 on Billboard‘s Hot Country Songs chart. It’s emblematic both of Nelson’s penchant for creative storytelling and his classic country croon, as he lends a showman’s touch to a metaphor-heavy song that would sound gimmicky in less capable hands. The track, which Nelson wrote himself, features the plaintive pedal steel of Tommy Jackson, with famed rockabilly musician Tommy Allsup handling production duties. The song has had many incarnations, from Nelson’s original recording to a 1982 cover by Merle Haggard (on Going Where the Lonely Go) to a re-recorded duet with George Jones included on Half Nelson.

Few songs, standards or otherwise, get touched by Nelson without forever bearing his likeness. Well, except possibly songs that had already been done by Ray Charles. So it’s a testament to both men’s skills as master interpreters that they could take “Georgia on My Mind” – already the official song of the Peach State – and make it their own. Nelson took his cue from fellow Atlantic Records man Charles (who was himself a Georgia native), giving his version a decidedly soulful reading on 1978’s Stardust, itself a sign of how far outside country he was willing to reach at the height of his outlaw notoriety. He wound up winning a Grammy for Best Male Country Vocal Performance for it, which was only deserved; his brittle, plaintive performance is one the finest Nelson ever put to tape, a masterstroke of emotional understatement. 

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.

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.

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.  

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.

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.