“Blue Eyes Crying in the Rain” was Willie Nelson’s first Number One as a singer. Patsy Cline’s version of Nelson’s “Crazy” is on the Library of Congress’s National Recording Registry. And “On the Road Again” ranks as the quintessential traveling sing-along, played everywhere from bars to ballparks. Even casual fans know those songs by the Red Headed Stranger. But dig deeper and there’s a whole other Willie to discover. Here are 20 obscure, but no less great, tracks that help shine a light on the full Nelson.
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 envelopes 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.
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."
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."
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.
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.
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.
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.
“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.
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.
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.
Like the Doobie Brothers are doing now, the Beach Boys recruited a group of country stars — well, mostly stars — to interpret their catalog on 1996's Stars and Stripes Vol. 1. Nelson may have been the unlikeliest of choices to tackle Brian Wilson's "The Warmth of the Sun," but the finished product was nothing short of sublime. Nelson's quavering voice conveys all of the heartbreak of Wilson's tortured teen verses, before the chorus arrives with its warming solace. "I get tears," Wilson said upon witnessing Nelson's performance in the studio. "That's absolutely phenomenal."
In 1997, Nelson and Johnny Cash taped an episode of VH1's concert-and-conversation series Storytellers, which was released the following year as an album. An often-overlooked record, Storytellers captured two of the Highwaymen in their element, with just their guitars and their own words. The album's opener, however, was one that neither man wrote: the Western fable "Ghost Riders in the Sky." Cash was his typical rock-solid self, his baritone summoning the song's spirits. But Nelson's vocal eclipsed Cash's gravitas, as it issued a fragile warning of cowboys "trying to catch the devil's herd, across these endless skies."
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.
An unabashed polka fan, Nelson has recorded "The Beer Barrel Polka" on 1983's Tougher Than Leather and collaborated more than once with polka king Jimmy Sturr. Together, they've reinvented Bob Wills' "Big Ball's in Cowtown," for Sturr's Polka! All Night Long album, and Nelson's own "On the Road Again," on Sturr's Grammy-winning Gone Polka, as accordion-driven rave-ups. But it's the majestic beauty of their "Waltz Across Texas Waltz" that best illustrates the happy cross-cultural union between the Lone Star State and Eastern Europe.
For 2002's The Great Divide, Nelson partnered up with artists ranging from Kid Rock to Rob Thomas for a mostly forgettable — and unfortunate — collection of duets. But all was not lost: Nelson and guitarist Jackie King, who toured with Nelson for a spell, penned a gem of a title track. Best of all, Willie recorded it all by his lonesome. Like much of the outlaw's best work, the Western ballad is cinematic in its scope, evoking a journey across the endless landscapes of a John Ford film. Only in this instance, Nelson is trekking in vain, in search of a relationship lost in that storied great divide.
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.
Ryan Adams produced Nelson's 2006 Songbird album, on which Nelson covers Gram Parsons' marriage-ceremony lament "$1,000 Wedding." On first listen, the interpretation of the Grievous Angel standout seems cacophonous, with its crunching guitars and Nelson's loose command of the verses. But cast Parsons' original from your mind and go along for the ride, allowing Nelson to play the role of narrator of a wedding gone wrong. How wrong? The bride up and goes missing. By the time Nelson sing-speaks "it's been a bad, bad day," you'll wonder why anyone ever tries to get married in the first place.
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.
The Son of God and the Duke get equal billing in this wild plea for peace, as Nelson asks for Jesus to return and save our crazy world — and “pick up John Wayne on the way.” Written by Nelson with son Micah Nelson and producer Buddy Cannon, the song, from 2012’s Heroes, is irreverent Willie at his best. No matter your politics or which deity you acknowledge, Nelson’s musical prayer is one that warrants an “amen.”
Married four times, Nelson would admit to being a ladies' man. And he does just that in this deliciously tongue-in-cheek toast from his latest album, Band of Brothers. "I love my wives/and I love my girlfriends/and may they never meet," the song begins, before unspooling a running tally of wives. Some were fine, some made him sick and one even caught him with his pants down — naturally, the protagonist barely made it out alive. True or not, Nelson has great fun inhabiting the part of philandering raconteur. In the end, he ultimately shrugs it all off: "I might be a Mormon/or I might be a heathen," he sings, "I just don't know."