The 50 Best Willie Nelson Songs

Much of the fun in this rollicking, honky-tonk favorite is in its musical variation on “puff puff pass,” as Nelson intros the song then steps back to leave the verses to Snoop Dogg, Kris Kristofferson and Jamey Johnson. The communal spirit clearly affected the song’s creation, too, as Nelson wrote it with longtime collaborator Buddy Cannon, as well as Rich Alves, John Colgin and Mike McQuerry. Nelson performed the song in Austin on April 20th, 2012, the same day an eight-foot bronze likeness of the Texas icon was unveiled. “I’ll be stoned one thousand years,” he joked to Texas Monthly.

Don’t think too hard on what the everything-is-Zen title means — your head will spin as if you just shared a joint with its author. Instead, meditate on the transcendent strumming Nelson practices on his trusty “Trigger” and the mantra-like “la la la” chorus he chants. A runaway train of a song, “Still Is Still Moving to Me” has become an unlikely staple of the Country Music Hall of Famer’s concerts, currently sandwiched right between show opener “Whiskey River” and the Toby Keith novelty “Beer for My Horses.” And judging by the response it garners nightly, its high-profile slot is — still — warranted.

Both signed in the mid-Sixties to Nashville’s Monument Records, Willie and Dolly (plus onetime Monument signees Kris Kristofferson and Brenda Lee) helped pay tribute to the label’s founder Fred Foster by participating in an album titled The Winning Hand. Nelson’s voice blends beautifully with Dolly’s on the gentle tune she first recorded in 1967, accentuating the sweet-natured lyrics and the two artists’ contrasting but perfectly matched styles. A 1983 TV special hosted by Johnny Cash was highlighted by this inspiring collaboration. The pair recently reunited on Nelson’s Monument-era tune, “Pretty Paper” for Parton’s A Holly Dolly Christmas LP.

The 2005 reggae lark Countryman, though a labor of love for Nelson, had all the staying power of a waft of smoke. But it did feature the definitive Willie version of the Jimmy Cliff classic “The Harder They Come.” Nelson had already been performing the song live, sometimes with Ryan Adams, but he never sounded as relaxed and yet so in control as he did on this studio version. The lyrics may advocate rebellion and raging against the man, but for Willie, everything was irie.

It fits that Willie’s biggest non-duet hit of 1984 — a year in which “America” was an explicit topic of songs by artists ranging from R.E.M. to Bruce Springsteen to Lee Greenwood — was the one that shouts out the nation in its chorus. Nelson’s cover of Steve Goodman’s “City of New Orleans”—which the Chicago singer-songwriter released in 1971 and Arlo Guthrie first took to the charts in ’72—streamlines Goodman’s woolly arrangement and pushes the vocal melody upward, making the whole thing more straightforwardly triumphant. The song takes its name from a classic Amtrak train line, and is written from the train’s POV as well. Nelson’s retooling turned its central hook line, “Good morning, America, how are ya?,” into a reflection of the year’s sunny national mood: “City of New Orleans” hit number one the week of Ronald Reagan’s landslide presidential re-election.

It’s one thing to sing, “The end is not the end at all,” in a song about grieving the loss of love—you know, you’ll live. It’s quite another coming from a man in his mid-eighties, as Willie was when he released this song—the highlight of a concept album about aging, Last Man Standing, no less. Here, that line indicates that everything will end. Nelson puts it, and the song, across with a quiet rue that’s also cunningly conversational—and genuinely pained

Absent from the country Top Forty for 12 years, Willie returned to the upper reaches of the singles chart with this eventual Grammy winner, penned by Bernie Taupin and Matt Serletic. For this wistful reflection of a failed romance, Womack provides the soaring vocal build-up then leaves Nelson to shine at his poignant best. The album which supplied it, The Great Divide, earned mixed reviews for its slick adult-pop production, but Nelson’s voice, as warm as a Pacific Ocean breeze, offers calming reflection.

When the tireless road warrior pushed his luck a little too far and illness forced him to cancel some gigs in the early part of the century, Nelson didn’t take it lying down. Instead, he wrote this tongue-in-cheek ditty about the fallacy of invincibility, which appears on the 2009 compilation Lost Highway. “Too many pain pills, too much pot, trying to be something that I’m not,” Nelson sings in yet another live favorite, which, like “Devil in a Sleepin’ Bag,” directly addresses ill health on the road. “I blew my throat and I blew my tour/I wound up sipping on soup du jour,” he rhymes. Hey, at least he’s honest.

Nelson explored his inner bluesman on 2000’s Milk Cow Blues, an album of duets and jams with Dr. John, B.B. King and Jonny Lang. Often, such projects outside an artist’s comfort zone can feel forced, if altogether inauthentic. But Nelson rejoiced in getting greasy, setting aside his battered Martin acoustic for a headless electric. It might have been jarring to see him without “Trigger” around his neck — like catching your father with someone other than your mother — but the resulting title track in particular proved Nelson’s love affair with the blues was no dalliance.

Written by fellow Texan and pal Steve Fromholtz (who sings backing vocals sounding like he only sort of knows where he’s supposed to come in) and sporting that wobbly electric guitar that was all over Seventies outlaw country, “I’d Have to Be Crazy” is an ode to oddness, specifically Willie’s own (“I have to be to grow me a beard/ just to see what the rednecks would do”). But he sounds downright gentle here, his voice a hand on your cheek as you slow dance on the bar floor.

“The title…is already intriguing,” Vince Gill said of this classic in a 2022 interview. “The very first line…just completely takes your attention.” That line is “They’re working while I’m missing you/ Those healing hands of time,” and it could be a declaration that an old lover will be just fine now that the couple is through, but the song itself has also aged into a statement of comfort in the face of tragedy. This first version was produced with spare restraint by Chet Atkins, but Willie revisited it several times, adjusting the emphasis over the years as time has morphed its meaning.

A Merle Haggard song that Nelson didn’t even record, “Workin’ Man’s Blues” makes this list because of the esteemed place it held in the Willie Nelson & Family live show. Often coming early in the set, Nelson would cede the spotlight to salt-of-the-earth guitarist and harmony singer Jody Payne, who tackled the Hag’s blue-collar anthem with been-there/done-that authenticity. The performance gave the boss some time to rest his voice — but never his fingers. Nelson’s playing during Payne’s interlude was always particularly inspired. Sadly, Payne, who also duetted nightly with Nelson on “Seven Spanish Angels,” passed away in 2013.

Producer Billy Sherrill wanted “Seven Spanish Angels” for Ray Charles, although Nelson already had it on hold. Sherrill’s solution to make it a duet would prove a sterling example of the musical versatility at which the two superstars excelled. A riveting, violent ballad in the tradition of Marty Robbins’ “El Paso,” the hero and heroine of this one die together in a hail of gunfire. But the songwriters also penned a never-released bridge for the tune, offering a relatively happier ending as ghostly visions of the reunited lovers are spotted in the night sky. It became Charles’ sole country chart-topper.

A love letter to Nelson’s birthplace, “No Place But Texas” is so rich with scenic imagery it makes even the most blue-blooded Northerner consider pulling up stakes and relocating to the Lone Star State. Written by Alex Harvey — who also penned Tanya Tucker’s “Delta Dawn” — the harmonica-heavy travelogue sounds tailor-made for the Texas tourism board. The song also lays out the author’s burial wishes. Whether they are Harvey’s or even the Red Headed Stranger’s authentic requests, or a bit of artistic license, to hear Nelson sing “When I die, I hope they bury me/on the Pedernales River/beneath a live oak tree,” is to confront the inevitable: that country music will one day feel a loss of Texas-sized proportions.

The title track to Nelson’s 1972 album, the cover of which features an out-of-place Nelson lugging his own guitar while a chauffeur holds the door of a waiting Rolls-Royce, is an honest admission that a romance is no longer working. One of Nelson’s more direct breakup songs — no veiled metaphors here — the lyrics plainly state that there’s “no need to force the love scenes.” Rather, “this is the time to say goodbye.” It’s Nelson at his most stark, refusing to feign a smile, turning out the lights and, like the title of his 1967 single, admitting “the party’s over.”

“I guess one of the reasons I’m so well known in Texas is, I’ve worked all these joints at least once,” Willie told Joe Nick Patoski in 1974. “I know practically every bartender in the state that ever pulled a cap on a bottle of beer.” And they knew him, from the sound of this raucous instant standard. A classic country drinking song, “I Gotta Get Drunk” was one of his last recordings before he left Nashville for Austin in 1971. Its lyric takes the long view: Willie walks us through his list of eventual post-drinking regrets ahead of time. Then he gets drunk.—M.M.

Arguably the funkiest Willie has ever been, “Devil in a Sleepin’ Bag,” from 1973’s Shotgun Willie, slinks along like a snake covered in motor oil. A recount of a tour gone bad — the band gets pneumonia, the bus loses a wheel — the song name-checks Nelson’s then-wife Connie Koepke and Kris Kristofferson and his wife Rita Coolidge, giving the lyrics a decidedly autobiographical slant. But that titular devil isn’t Ol’ Willie. It’s Nelson’s nickname for his long-time consigliere and drummer, the intimidating Paul English, who with his Van Dyke beard and long sideburns looked the part of Beelzebub. Check out the cover to 1971’s Willie Nelson & Family, with English sporting a dashing yet devilish red cape.

Adonred with hand percussion, Sister Bobbie’s organ, and Emmylou Harris’s backing vocals, the 1998 version of “I Never Cared for You” hails from Teatro, produced by Daniel Lanois (the video for this one opens with a masterful, jazzy solo on Trigger absent from the album). But great interpretations from the writer abound. It became a live staple. You should also check out the flamenco-ish, 1964 single version he recorded for Monument, where our man practically snarls the lyric, a kiss-off up there with Dylan’s “Idiot Wind.” “I know you won’t believe these things I tell you,” he sings. “No, you won’t believe/Your heart has been forewarned all men will lie to you/And your mind cannot conceive.”

With his behind-the-beat phrasing, Nelson has never been considered a traditional vocalist, but his performance of this cinematic Red Headed Stranger track, penned by Bill Callery, is without peer. Nelson reaches and holds notes that grab you by the denim collar and don’t let go — a case can be made for the line “there’s deceivers, and believers and old in-betweeners” being one of Nelson’s all-time best vocal runs. The song also appeared on the soundtrack to 1979’s The Electric Horseman — which costarred Nelson in his first movie role — playing over the closing credits as Robert Redford’s restless cowboy Sonny Steele walks off with no particular place to go.

Nelson’s 1971 Yesterday’s Wine album is rife with bittersweet nostalgia, from the reminiscing-over-a-bottle title track to the heartbreaking “Summer of Roses.” But it’s “December Day” that paints the starkest picture of a man taking stock of his year — and a relationship. The artist, still evolving into the long-haired troubadour he’d become, sings of “a time to remember day” and “a spring, such a sweet tender thing” like a country music Sinatra. “December Day” is Nelson’s “It Was a Very Good Year,” full of poignancy and tinges of regret. It also defines the Christmas month as the saddest of all, something Haggard realized two years later with “If We Make It Through December.”

At 70 years old, Willie Nelson became the oldest artist to score a Number One country hit for his participation on this million-selling Toby Keith and Scotty Emerick-penned tune, which essentially documents generations of vigilante justice. Taking its key line from a scene in which actor Jan-Michael Vincent and his horse saunter up to a saloon bar in the 1975 Western Bite the Bullet, the song would inspire a funny music video starring Keith, Nelson and young actor Corin Nemec. A later feature film with the two game country stars would net a “zero” rating at movie review site Rotten Tomatoes, but there’s no denying the song’s catchy-as-hell chorus.

Originally released on Nelson’s very first LP, 1962’s …And Then I Wrote, this tale of a love who leaves is drama to the hilt: She splits, the sun explodes and darkness envelops the land. It’s almost biblical in its apocalyptic vision of a world without love. Nelson revisited the song three years later on his Country Willie: His Own Songs album with a slightly different feel. In 1998, he returned to “Darkness” yet again for the Daniel Lanois-produced Téatro, ramping up the haunting quality of the lyrics with a percussion-heavy, hypnotic arrangement. But it’s his original 1962 version, and a performance from that era on The Porter Wagoner Show, that best conveys the earth-shattering hopelessness that can follow a breakup.

With just a traditional country beat and three-plus minutes, the ever-defiant Nelson offered the ultimate “fuck you” to the Nashville suits. Originally recorded as a duet with Waylon Jennings for the 1982 collaboration album WWII, Nelson cut his own version for the soundtrack to his 1984 film Songwriter. Both pack the same slap-in-the-face wallop, however, with Nelson singing directly to “Mr. Music Executive” and his ilk, beseeching them to mind their own damn business and let the artists do their job. At one point, Nelson even asks, “Is your head up your ass so far that you can’t pull it out?” Music Row, you got owned.

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.

It dates from the the old, weird America of the late 1800s, and has been covered by everyone from Doc Watson to Don Henley, and sounded downright otherworldly when the Stapes Singers recorded in 1956, but in Willie’s hands, “Uncloudy Day” is nothing but joyful, a warm, jubilant welcome into the comfort of faith and the glory of God’s creation. Knocked out in 1973, it sat around until it kicked off The Troublemaker in 1977 and promptly became a country hit in the wake of the Red Headed Stranger’s success a year earlier, quite a feat for a gospel tune.

“My American dream fell apart at the seam,” sing Nelson and Bob Dylan in this elegy to America’s family farmers. A track from Nelson’s 1993 Across the Borderline, the song details in plain language the war between forlorn farmers and unsympathetic bankers, with the latter undeniably the victor. Willie wrote the song with Dylan, who famously inspired Nelson’s annual Farm Aid benefit concerts with his off-hand remark at 1985’s Live Aid that something should be done to help U.S. farmers. The lyrics are unapologetic, brimming with as much indignation as Mellencamp’s “Rain on the Scarecrow,” but it’s the pairing of two of music’s most unconventional voices that makes it a must-hear.

Nelson’s Nashville Sound years — strings, choirs, earnestness—are often dismissed because they don’t fit the tougher, sparer musical framework he’d come up with after moving to Austin in the early Seventies. But not only is this song so durable it stands up to just about any kind of treatment, the verses are sparse and dramatic, and so are Willie’s vocals. He underlined the song’s place in his catalog when he climaxed his performance for the pilot episode of Austin City Limits with it—and reprised it when he returned to the show this past February, 50 years later.

“I discovered a new audience of young people,” Nelson said in 1978 of his mid-decade commercial efflorescence. “So, I started playing to and for that audience. But I didn’t do anything to offend my old audience, so I didn’t lose any of the fans I’d had for a while . . . When they all got together, that’s when I started to sell some records.” By 1976—thanks to Red Headed Stranger and Wanted: The Outlaws, both bestsellers—Nelson was a country superstar. His sweetly swinging resurrection of the classic Lefty Frizzell drinker from 1950—highlighted by a high-stepping piano solo from sister Bobbie—topped the chart, Nelson’s second ever country number-one as a performer.

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 gloriously cheesy pop- and Latin-flavored tune was a crossover phenomenon in 1983, earning Spanish heartthrob Iglesias his English-language breakthrough. The song made a globally recognized romantic out of Nelson as well, earning Top Twenty status in the U.K., his biggest hit there (not including his participation in the 1985 Number One, “We Are the World”). The pair returned to the country charts in 1988 with a Top Ten cover of the oft-recorded “Spanish Eyes.”

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.

Written and recorded a few years before Red Headed Stranger kicked off Willie-mania, “Yesterday’s Wine” is the title track of that concept album about an “Imperfect Man” contemplating his faith. Filled with conversational little guitar riffs, Willie opens with “Miracles appear in the strangest of places/fancy meeting you here” and one is unsure if he’s talking to an old pal he’s run into a local watering hole or the Lord or both. Released as a single, it tanked at the time but George Jones and Merle Haggard, who knew a thing or three about being the old guy at a bar, scored a hit with it in 1982. 

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.

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.

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.

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.

Atlantic Records co-founder Jerry Wexler had never signed a country act until he heard Willie. In his autobiography, Wexler compared Nelson to Sinatra for his “gift for incredible vocal rubato—prolonging one note, cutting short another, swinging with an elastic sense of time that only the finest jazz singers understand.” The first of two albums Nelson made for Atlantic features a title track that explicitly and effortlessly drew the lines between Wexler’s world (the horn arrangement, a Nelson rarity), and Willie’s, from the terse guitar solo to a lyrical portrait of a titular antihero “sitting around in his underwear.”—M.M.

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. 

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.”

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.

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.

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.

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.

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.

It’s no coincidence that rock & rollers like B.B. King and David Lee Roth have all 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.

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.

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.