In my favorite scene in the otherwise middling Notorious B.I.G. biopic Notorious, the corpulent wordsmith (played by amusingly named newcomer Gravy) tries to atone to his stern, country-music-loving mother for his drug-dealing, school-ditching ways by buying her the corniest-looking album he can find: Willie Nelson’s Greatest Hits. It’s a moment rich with irony, for Shotgun Willie was/is the coolest motherfucker on the planet.

B.I.G.’s mother says she loves listening to country music “because it tells good stories.” Amen. Willie Nelson became a towering American icon because he told good stories. The same is true of Notorious B.I.G. The emotional directness of country and hip-hop lends itself to ambitious narratives and autobiographical storytelling.


You cannot be a good American and not like Willie Nelson. It’s one of the prerequisites for citizenship. There is actually a multiple-choice question on applications for U.S. citizenship that reads:

What do you think of Willie Nelson?

A. I don’t care for him or his music. Also, he promotes the deplorable practice of smoking marijuana, which I find offensive.
B.   Eh, he’s okay, I guess.
C. He is a goddamned national treasure. All hail Willie! Whiskey River take my minnnnnnnd…


Answering A or B earns would-be Americans a one-way trip to the gulags of Siberia, whether they come from Russia or not. I’ve always liked Willie, but I started to love the holy fucking fuck out of him when I picked up the promos for his box set, One Hell Of A Ride, out of the A.V. Club promo pile about a year ago. How had I gone my entire life without hearing songs like the following?


I was beyond smitten. I found myself asking, “Where have you been all my life?” But Willie’s awesomeness wasn’t exactly a secret. Willie has been around since the beginning of time. He is the Alpha and the Omega, the yin and the yang, Milli and Vanilli. Sorry if I got a little hyperbolic there. There’s something about Willie that inspires over-the-top devotion. His voice has ricocheted non-stop through pop culture for the last three and a half decades. Nelson was just an integral part of a world I hadn’t paid much attention to. It’s inspiring and daunting to realize that no matter how rapaciously you consume pop culture, there will always be vast universes of art and entertainment out there you’d love if you only gave it a chance. You could live to be older than Methuselah and still only experience a fraction of the awesomeness the world of pop culture has to offer.


Ride made me want to dig much deeper into Willie’s past and country music as a whole, even if I had to embark on some sort of elaborate yearlong online project to justify my quest. Ride consequently served as a terrific gateway to country geekery, just as Willie’s beloved marijuana is a gateway that inevitably leads to injecting heroin into your eyeballs and selling your newborn for crack money.

Ride is a wonderful place to start with Willie, though it seems perverse to recommend a compilation for such a consummate album artist. Nevertheless, the sheer volume of material Nelson released can be intimidating to newcomers, and Ride does a good job cherry-picking the highlights of Nelson’s unimaginably ginormous catalog. Willie has a hip-hop approach to recording and releasing new material. He records fast, voluminously, and indiscriminately, on countless labels, major and independent.


Willie will record a duet with anyone. Then again, why limit yourself to a song when you can record an entire collaborative album together? (Or two. Or three.) Willie’s the kind of guy who’ll record an album of duets with Louis Farrakhan in the morning, the Grand Wizard of the Ku Klux Klan in the afternoon, and Yitzhak Perlman in the evening. Willie don’t give a mad-ass fuck. Even T-Pain is all, “That man needs to be more selective in terms of who he records with.”

If Johnny Cash presided over a vast sonic kingdom of darkness, then his fellow Highwayman Willie Nelson is all about good vibes and positive vibrations. If reading about Cash is harrowing, immersing yourself in Nelson’s life and music is heartwarming, even life-affirming. Verily, Willie is like a God. At least that’s the conclusion hagiographer Joe Nick Patowski reaches in Willie Nelson: An Epic Life. In a three-page stretch, Nelson is compared, without irony, to Buddha, the Dalai Lama, and Jesus. In Patowski’s worshipful telling, even Nelson’s faults are rooted in his virtues—his excessive generosity, his unshakeable belief in the goodness of human nature, and his willingness to trust people he shouldn’t.

Nelson liked telling stories so much that much of his ’70s heyday was devoted to telling narratives so big and expansive that a single song couldn’t contain them. So he released one perversely downbeat concept album after another until miraculously, one of them made him a huge star. Because Nelson’s career is too sprawling to do justice to in a single entry or two, I’ll be making Willie’s ’70s concept albums the focus of the fourth week of Nashville Or Bust.


If it’s a mark of insanity to do the same thing repeatedly but expect a different outcome, then Nelson must have been half-mad to peddle Red Headed Stranger, an ambitious, melancholy concept album, to an industry and public that roundly rejected his last two, 1971’s Yesterday’s Wine and 1974’s Phases And Stages.

Nelson’s predilection for concept albums began with the mind-meltingly odd Yesterday’s Wine, a spacey oddity about a man looking wistfully back at his life at the behest of his heavenly bosses. It opens with the following stiffly recited spoken-word banter between its narrator (let’s just call him Willie Nelson) and his otherworldly overlords:

Heavenly Voice: You do know why you’re here.
Willie Nelson: Yes. There is great confusion on Earth and The Power That Is has concluded the following: Perfect Man has visited Earth already and his voice was heard. The voice of Imperfect Man must now be made manifest, and I have been selected as the most likely candidate.
Heavenly Voice: Yes. The time is April, therefore you, a Taurus, must go.
Second Heavenly Voice: To be born under the same sign twice gives strength.
Other Heavenly Voice: And this strength, combined with wisdom and love, is the key.



It might be germane to note that at this point in his career, Nelson had fled the formulaic, homogenous world of Nashville, grew a beard and long hair, developed a shockingly non-regrettable fondness for bandannas, and cobbled together an idiosyncratic worldview that combined old-school Christianity, humanism, a New Age spiritual discipline known as “Astara,” and progressive politics. Also, he was smoking a shit-ton of weed.


Nelson tuned in, turned on, and dropped out. It wasn’t until he traded in Nashville for the hippie scene in Austin that he found himself and his voice as a performer. Nevertheless, the world was not yet ready for Yesterday’s Wine, a downbeat collection of story-songs about the passing of time and a man/cosmic being taking a good long look at his back pages with fondness and regret.

The album begins with Willie Nelson being, um, sent to Earth so that the Voice Of The Imperfect Man can be made manifest, and it ends with its narrator contemplating his impending death/funeral with aching anticipation on “Going Home.” Nelson was only 38 when he recorded Yesterday’s Wine,yet it feels intentionally elegiac, the work of a wise old soul in a middle-aged man’s body. Its sustained tone of wistful regret is expressed most eloquently in the title track:


Yesterday’s Wine is almost too hushed and somber for my tastes, but it does have an undercurrent of wry good humor. “Me And Paul” is one of my top five favorite Willie Nelson tracks, a wonderfully understated touring song that captures with novelistic detail and wry comedy the rambling rhythms of the road and what it feels like to be a mid-level journeyman wondering if your day will ever come.

I don’t want to get bogged down in digressions here, but I would like to share the following information about Paul English, Nelson’s longtime drummer, best friend, badass, consigliere, and the subject of “Me and Paul.”


1.    Before he became Willie Nelson’s drummer, Paul English was a pimp. Literally. English’s gift for getting disreputable underworld types to part with money proved invaluable when dealing with shifty club owners. As the movie Anvil: The Story Of Anvil reminds us, it never hurts to have a badass in your entourage willing and eager to put the fear of God in promoters if they even think about short-changing you.

2.    English cultivated his resemblance to Satan by growing a pointy beard and wearing dramatic capes onstage. English’s sinister fashion sense inspired Leon Russell to write “You Look Like The Devil In The Morning.”

3.    During his pimping days, English was an associate of a crime boss nicknamed “The Cat” because he survived nine attempts on his life in a single day, only to be blown up starting his car the next morning.


Yesterday’s Wine would have been a risky project for a multi-platinum superstar. For a cult act who’d written a slew of iconic hits (“Crazy” for Patsy Cline, “Night Life” and “Hello Walls” for Faron Young, “Family Bible” for Claude Gray, and “Pretty Paper” for Roy Orbison) but had little success as a recording artist, it was downright insane. Undeterred by Wine’s failure, Nelson released 1974’s Phases And Stages, a concept album with an even less commercial theme: D-I-V-O-R-C-E.

With Stages,Nelson accomplished the formidable feat of making an album about divorce that isn’t depressing. It says much about Nelson’s early tendency toward melancholy that of his three major ’70s concept albums, Stages is easily the peppiest of the bunch. Stages sees divorce as a beginning as well as an ending. It’s an album about the overlooked glory of survival and the casual resilience of the human spirit.


Stages is as committed to celebrating a new beginning as mourning love lost. It’s optimistic and hopeful without shortchanging the emotional wreckage that invariably accompanies divorce, though it wasn’t helped by a title that belongs on the front of a brochure about coping with menopause, instead of a country album.

From the first track onward, Phases And Stages confirms Nelson’s genius for mining heartbreak and drama out of the stuff of everyday life. Casting an empathetic eye on both halves of a divorce, Nelson softly sings, “Washing the dishes / scrubbing the floors / caring for someone / who don’t care anymore” like a wandering minstrel of domestic despair.


The first half of Phases And Stages tells the wife’s side of the story, and the second tells the husband’s. Phases is less concerned with what happened and why than with what’s next. In “Sister’s Coming Home/Down At The Corner Beer Joint,” the wife tries to reestablish her sense of self outside the confines of the marriage that has defined her for so long, while in “Bloody Mary Morning,” the husband acclimates himself to the bleary realities of his solitary new existence.


As a child of multiple divorces, I instantly recognized the rocky emotional terrain of Phases And Stages, the simultaneously terrifying and exhilarating sense of possibility that comes with the dissolution of a marriage. As I was growing up, my father had two big pieces of advice for me: Don’t get married, and don’t go to University Of Chicago. (My grades and test scores made not going to his hated alma mater a cinch.) During every breakup, my father’s sage counsel was the same—“At least you didn’t make it legal.” So was my response, “Jeez, Dad. Thanks.”

There is something soothingly familiar about Willie Nelson, an effortless emotional intimacy that makes it easy to imagine he’s singing directly to you. Listening to Red Headed Stranger is like sitting around a crackling campfire while Willie strums his acoustic guitar and sings songs of heartbreak and rambling.

Willie diligently built a grassroots fan base by wowing live audiences, wooing Texas radio (he was a radio personality himself in his pre-stardom days) and spending hours every night signing autographs and talking to fans. Willie always had the songs, the talent, and the work ethic. He’d put in the work. Now he just needed the album and hit single that would put him over the top.


Nelson’s popularity was primed to explode nationally, but Red Headed Stranger was the unlikeliest of blockbusters, a moody downer from an artist twice as old as the pimply teens whose conspicuous consumption drives the record industry.

I can only imagine how Columbia’s executives must have reacted to news of Red Headed Stranger. In my mind, it went a little something like this. (Cue up the Hacktometer 3000 hypothetical conversation generator!)

Executive 1: Hey, you know Willie Nelson, that weird middle-aged singer-songwriter hippie who did all those weird, depressing concept albums that flopped? He’s got an idea for his next album.
Executive 2: Oh goody!
Executive 1: You’re going to love it! It’s a weird, depressing concept album about a preacher in the Old West who kills his wife after finding her with another man. He is then cursed to roam the country, toting his dead wife’s beloved pony alongside him.
Executive 2: Good Lord. At least we can sick strings all over it and hope people ignore the concept.
Executive 1: No, I’ve been listening to some of the tracks, and it’s largely just Willie and an acoustic guitar and piano. It almost sounds like a demo. You know that awesome, ass-kicking live band Willie’s got, that band everyone loves that has helped make Willie a big live act in Texas?
Executive 2: Sure. Those guys are great.
Executive 1: Yeah, they’re pretty much sitting this one out. It’s just going to be Willie, a guitar, a piano, maybe a lonesome harmonica here and there, and then this weird, melancholy story of murder and guilt.
Executive 1: Sounds like a very artsy tax write-off.


Oh, how the scoffers scoffed! Columbia had a hard time reconciling the Willie that kicked ass in concert with the somber, folksy troubadour of Red Headed Stranger. According to show-biz legend, the bean counters over at Columbia saw the recording bills for Red Headed Stranger and thought a terrible mistake had been made. Surely a major-label album from a major artist couldn’t be made for such a tiny sum of money. But years in the Nashville trenches had taught Willie to work fast, cheap, and loose.

The skeptics predicted doom. Why did Willie expect Stranger to succeed where Yesterday’s Wine and Phases & Stages failed? I will concede here that I too was underwhelmed upon hearing Stranger for the first time. It did not live up to its vaunted reputation. Where were the songs? Where was the energy? Why was it all so goddamned morose and sad?

But the more I listened, the more I liked it. For Stranger is a concept album in the truest sense, with recurring lyrical and musical motifs anchoring a relatively straightforward narrative about a tormented nowhere man who catches his wife with another man, murders her, then travels the West with his dead wife’s beloved pony trailing behind him, a galloping symbol of his guilt.


Like American Recordings, Red-Headed Stranger strips Willie’s aesthetic down to its essence. It’s a bravely minimalist, short (just over 30 minutes) revisionist Western in song-cycle form, a melancholy mood piece of subtle insinuating power. The success of Red Headed Stranger and its monster single “Blue Eyes Crying In The Rain” cemented a disgustingly all-American success story about an artist of voluminous talent and integrity who maintained faith in himself and his creative vision in the face of considerable failure and resistance. It’s the story of an iconoclast who kept pushing and pushing until he finally, permanently broke through. Willie conquered the world, yet retained a common touch. The Voice Of Imperfect Man was made manifest. The key to Willie’s success, I’m convinced, is strength combined with wisdom and love, not to mention the timeless appeal of a good man telling good stories.

Up Next:

Willie Nelson’s Genre-Hopping Endeavors

Gram Parsons’ Cosmic Musical Americana

Hank Williams

Bob Wills

Tom T. Hall

The Louvin Brothers