While reflecting on the sexual politics of small-town Texas life, the novelist Larry McMurtry once mused on the stunted emotionality of the cowboy: “The tradition of the shy cowboy who is more comfortable with his horse or with his comrades than with his women is certainly not bogus… The cowboy’s work is at once his escape and his fulfillment, and what he often seeks to escape from is the mysterious female principle, a force at once frightening and attractive.” For male flatlanders, whose development can be as arrested as the arid land they inhabit, the two things can sometimes get confused for one another: women seen as wild beasts to be broken into submission, horses as precious creatures deserving of respect and affection, both treated with a certain caution lest you break your heart and bust your ass.

Like so many Texan poets laureate before him, Lyle Lovett’s songwriting has long been fixated on those two primary neuroses: the emotional relationships of men to the women they love—what he once bluntly characterized as “the male-female thing”—and the emotional relationships of men to the livestock they tend to. In a 1988 Rolling Stone profile, Lovett quipped that he would have been a cowboy, had he not been deeply afraid of cows: “My uncle had a dairy farm. I used to help milk them and stuff. But you get kicked a couple times and it sort of makes you get gun-shy.” The interviewer couldn’t help but make the obvious prod about Lovett’s bovine anxiety: “Sort of like with women?”

“If I Had a Boat,” the opening track to Lovett’s second album, 1987’s Pontiac, expresses that perpetual Peter Pan syndrome as a wistful cinematic fantasy: “If I was Roy Rogers, I’d sure enough be single/I couldn’t bring myself to marryin’ old Dale/Well, it’d just be me and Trigger/We’d go ridin’ through them movies/We’d buy a boat and on the sea we’d sail.” If the folky melody felt like it came from a much older place, the kind of big-rock-candy-mountain daydream a hobo might have strummed a generation ago, that’s because in some way it was. The song originated almost a decade before it was recorded, during Lovett’s tenure as a journalism student at Texas A&M University, written while playing hooky from history class. “If I Had a Boat” immediately felt like a country standard, destined for the secular hymnal every picker carries around in their head, if only because Lovett had played it so many times before he ever recorded it—the words and images came effortlessly, but he still took years to make sure they were just right.

Though his 1986 self-titled debut had made for a successful enough introduction to Nashville, it was Pontiac that announced Lyle Lovett as not just a voice worth listening to, but a vivid writer who wormed his way into your imagination. There was an old-fashioned twang to the swinging rhythms and weepy steel guitar of Lyle Lovett, but its production was also very of the time, electrified and synthesized and ready for the stage at Farm Aid. Pontiac stripped it all down to the core, developing the warm, organic sound Lovett would continue to refine, a blend between the acoustic intimacy of coffee-shop folk and symphonic jazz. By embracing his many idiosyncrasies as both a performer and persona, Lovett only seemed to make himself more loveable, and the unsinkable eccentricity of Pontiac made it a surprise hit outside country. The record may have had hybrid appeal, but it was still unmistakably Texan; somehow, Lovett’s refusal to take his boots off no matter where he roamed made him all the more appealing, even exotic, to those who might normally look down on cowpokes.

As a long, tall Texan born of upstanding Lutheran stock, Lovett had a surprising capacity for subverting relationship tropes in country music. In Lovett’s songs, the trappings of cowboy life can function as fetish objects. From the opening fiddle licks of “Cowboy Man,” the Western-swing wet dream that introduces his debut album, he gleefully embraced innuendo, turning a cowhand’s trusty lariat into an instrument of sexual bondage. The narrator of 1996’s “Don’t Touch My Hat” clings to his Stetson like a waifu body pillow, willingly choosing a hat that fits right over romantic fulfillment; the premeditated murderer of “L.A. County” finds platonic companionship with a firearm who “did not say much” on the drive to their deadly final destination. In the universe of Lovett, like the woeful wooden “Kaw-Liga” that Hank once sang of, objects are personified and persons objectified: the bleary-eyed bar patrons “unplugged” like a neon sign on “Closing Time,” or a woman played with like a turntable on 1994’s “Record Lady.”

There’s a casually absurd, almost childlike surrealism to Lovett, a man who has written songs about his affection for penguins and his distaste for pants. That borderline cartoonishness extended to his visual presentation, namely his hair, which from the inauguration of his career would be discussed by critics almost as much as his music itself. Robert Draper’s iconic 1992 Texas Monthly profile of Lovett would devote lots of ink not just to the “thatch of nuclear-radiated alfalfa sprouts” atop his head, but his face, which “suggests the elegance of an elephant tusk.” A review of Pontiac for the Associated Press posited him as “more like a Pet Shop Boy than an Oak Ridge Boy,” while Hank Hill put it more bluntly on an episode of King of the Hill: “Get out of my way, rooster boy.” When k.d. lang first met Lovett backstage at the Country Music Awards, she allegedly asked him, “Did you get into Eraserhead for free?” No matter which descriptor you chose, Lovett’s hair stuck out like a water tower on the horizon, far too large to be contained by even a ten-gallon hat. In some way, he seemed to mock his home state’s preoccupation with its own perception of big-ness, his hair an obelisk to the stubborn and endlessly self-mythologizing Texan, climbing ever higher alongside the oil wells and windmills and rockets that reach into the sky.

Music Row might have been afraid of Lovett, but they couldn’t look away. Playing songs from his debut album on a 1987 episode of Hee-Haw, he made for a dark contrast to the program’s yum-yucking y’all-come humor, a shifty-eyed drifter with a crooked grin staring straight into your soul. Hollywood couldn’t shake his gaze either. Lovett wasn’t fit to be a debonair leading man like Kris Kristofferson, or even Dwight Yoakam, but his mug was made for character acting, and Robert Altman would use him—much like Michael Mann employed Willie Nelson in Thief, or Tom Waits in the films of Jim Jarmusch—as a bit of local color in later-period works like Short Cuts and The Player. Lovett would also provide the toe-tapping Western swing score to Altman’s slight romantic comedy Dr. T & the Women, about a Dallas gynecologist whose wife has a psychotic break—a protagonist right out of a Lyle Lovett song.

For all his nose-thumbing at convention, Lovett held fast to certain traditions, like a shadow you just can’t shake. In spite of the bright Hollywood lights and Nashville bigwigs that courted him, Lovett has continued to live all the while in his hometown of Klein, a once-rural and now-suburban community just north of Houston, founded in the 1840s by Lovett’s own German immigrant ancestors. By the time of Lovett’s childhood in Klein during the tail end of the baby boom, the land had been completely remade by oil and its interests. The Texas mud gave rise not only to thunderous swells of petroleum, but a metaphorical range war of simmering resentments, between the roughnecks who rushed after oil and the ranchers who wanted to hold onto the old ways. Lovett grew up somewhere in between, learning how to rope and ride on his uncle’s farm while his parents worked at Exxon. The rhinestone cowboys he sang of on “Farther Down the Line” and “Walk Through the Bottomland” may have been colorful characters, but theirs was a reality Lovett was never too far removed from, as a lifelong breeder of horses and competitive rider inducted to the Texas Cowboy Hall of Fame in 2012. Much like Larry McMurtry, Lyle Lovett may have at times traded the ranch for high society, but you could never quite take the ranch hand out of him.

Lovett approached his development as a singer-songwriter almost like a practical apprenticeship. As a reporter for The Battalion, Texas A&M’s student paper, Lovett profiled Texan songwriters like Willis Alan Ramsey, Michael Martin Murphy, and Steve Fromholz, booking many of those same acts at clubs on campus—usually with himself as the opener. Lovett used his assignments for the school paper not only to pick the brains of his idols about their craft, but sometimes even to learn songs directly from them. For all his eccentricities, Lovett approached songwriting like a journalist, detailing scandalous crimes and human interest stories alike with a mindful precision, always careful of the word count. The result landed somewhere between magical realism and creative nonfiction. Looking back at Pontiac in 2018, he explained that “Simple Song” was written like an assignment for English class: “It was the five-paragraph paper. Opening paragraph, three more paragraphs, and then one that closes. I wondered if I could write a song that way.”

His idols like Guy Clark and Townes Van Zandt may have had more name recognition outside of Texas, but many of Lovett’s most beloved songwriters were practically artistic hermits, decidedly disinterested in whatever the music business could sell you. The city limits of Austin might have become synonymous with live music, but each corner of the state bore forth its own unique musical traditions: the electrified rockabilly and sparse Flatland songwriting of West Texas, the slick cowtown countrypolitan of the North Texas Panhandle, the 12-bar blues and Cajun flavors of deep East Texas, and the raucous Tex-Mex brew of the South Texas borderland. Lovett was an active inhabitant of this statewide musical ecosystem, regularly performing at events like the prestigious Kerrville Folk Festival.

Though it was his breakthrough to the pop charts, Pontiac felt like an elegy to something that would soon be gone, with Lovett’s face blurred into grayscale obscurity; that monochromatic design has marked his album covers ever since. The video for “If I Had a Boat” chaotically intersperses the song with Errol Morris-like interviews with the aging residents of Klein. “They’ll still be running cattle in Harris County in 25 years,” one of them opines. “It might be in the shade of a 20-story building, but there will still be some cows here.” The album’s title track sees the world through the tired eyes of one of these nameless old men, who luridly fantasizes of telling a young girl about all the Germans he killed in the war.

In both voice and instrumentation, Lovett sounded like his peers about as much as he resembled them. After a few too many critics described his style as “big band,” he began referring to the ever-growing orchestra that supported him as his “Large Band.” Their lush arrangements could have fit at the Cotton Club and the Armadillo World Headquarters alike, fiddle breakdowns rubbing shoulders with funky backbeats. The spirit of Bob Wills was regularly invoked by reviewers of Pontiac, but Lovett stood apart from the era’s neat-and-tidy neo-traditionalists, a proudly sore thumb next to the Sinatra-esque schmaltz of George Strait or the souped-up party music of Asleep at the Wheel. On a song like “M-O-N-E-Y,” Lovett swings at a slowly swaggering tempo, moving to a beat more suited to sweaty pelvic grinding than the nimble footwork of a line dance.

When not performing with the Large Band in their full form, Lovett is often backed by a minimalist ensemble, recalling a jazzier version of an old-time string band like the guitar and “hillbilly cello” combo of Norman and Nancy Blake. With a deliberate sparseness, the outfit works in hazy watercolors, underscoring “Pontiac” and “Simple Song” with a dewy glisten: velveteen acoustic guitar, Bruce Hornsby-esque clear piano lines, light brushstrokes of percussion, the resonant baritone of cello strings, and steel guitar that occasionally stretches out with the spaciness of post-rock. Whereas so many of his heroes sang with voices weathered and worn, Lovett’s felt more like cool creek water, clean enough to drink but not clear enough to see through.

Emotionally and musically, Lovett tends to work in extremes. For every comic romp or densely arranged composition, there was another more restrained and clear-eyed, heartbreakingly tender or haunting or somehow both. Maybe his tales of violence were all the more unsettling because of that gentle vulnerability, the shyness and self-effacing humor that made him seem like such a raised-right and well-mannered man. “L.A. County” is a tale of parallel road trips, as two pairs of “old friends” set off in search of something they’ve long dreamed of: the first, a woman and her silent male companion, who find love in each other’s arms after arriving in California and make a plan to wed; the second, a man—maybe a jealous ex-lover, maybe the angel of death—and his “coal black” pistol. For both sets of pilgrims, the far-off “lights of L.A. County look like diamonds in the sky,” the twinkling promise of a long-held dream finally within sight. Like The Graduate gone wrong, the man arrives just in time to observe the blissful scene—“Her face was bright as the stars a-shining/Like I’d dreamed of all my life”—before piercing it with a bullet, the crumpled bodies “kneeling at the altar.”

Lovett’s brand of humor was hardly new to Nashville country, but something about the way he piled on the irony while staring straight into your soul, lip twisted and hair tormented, gave songs like “She’s No Lady” a Lynchian menace. Because of his willingness to embody flawed male characters, at times not just unsavory or unsympathetic but downright lecherous, early albums like Pontiac were met with occasional accusations of misogyny—there was the spiteful violence, sure, and his willingness to mock a potential dance partner’s appearance on a song like “She’s Hot to Go” certainly didn’t help either. But like the scathing satires of Randy Newman—an influence who he would collaborate with later—Lovett would hand over the song’s perspective to more unsavory characters than himself. The protagonists of “God Will” or “I Married Her Just Because She Looks Like You” are unreliable narrators, imperfect men unable to overcome the cruel vanities of self-pity and pride to let love in. On Pontiac’s Tex-Mex-accented “I Loved You Yesterday,” Lovett pleads for his lover to take him back, yet places the blame for their relationship’s failure solely on her shoulders and takes no responsibility himself. That “fear of the mysterious female principle” Larry McMurtry once identified rears its head in songs like “Give Back My Heart,” in which a domineering redneck Jezebel towers over a shrimpy cowboy like an R. Crumb cartoon. (Per usual, Lovett acknowledged the perception of his gender politics only dryly: “Lately I’ve been thinking about taking some time off from the music thing and opening up a chain of misogyny parlors,” he joked in Rolling Stone.)

But the surface impression of misogyny doesn’t match up with the reality of Lovett’s music, which frequently emphasizes and even privileges the female perspective, not just in lyricism but in collaboration. The women who have lent Lovett their voices—like Emmylou Harris on “Walk Through the Bottomland” and “L.A. County”—are often high up in the mix, as true duet partners and not just backup singers. After Lovett’s long-time duet partner Francine Reed first sang on the Sunday morning service of 1986’s “An Acceptable Level of Ecstasy,” she was promoted to a featured player on Pontiac—she appears on “Give Back My Heart,” “M-O-N-E-Y,” and “She’s Hot to Go”—and subsequent albums would increasingly highlight her as an irreplaceable pillar of Lovett’s sound. Performing “Here I Am” alongside Reed on The Tonight Show, Lovett steps back and lets her take the lead like she’s the real star of the show, with nothing but adoration in his eyes. Johnny Carson was reportedly so captivated by the pair’s musical chemistry that he made the rare call to invite them back for a second performance only weeks after their first.

Beneath all the literary narratives and affected characters, it’s that unrestrained joy in group collaboration, the effortless electricity that crackles when performers are perfectly in sync, that Pontiac captured like lightning bugs in a jar. “If I Had a Boat” told of a man and his steed alone against the currents, but Lovett could have never existed in isolation—he needed other hands to pitch in and help raise the framework of his wooden universe. From those long hot afternoons in the late ’70s picking bluegrass tunes with his Texas A&M classmate and fellow songwriter Robert Earl Keen on up to the intricate spectacle of his well-oiled orchestra, Lovett’s music has always been a patchwork affair, passed around like an exquisite corpse as individual sensibilities combine anew. The years have a way of altering perspective, and Lovett now looks much more like the “weathered gray-haired seventy years of Texas” he sang of as a young man. But well-crafted songs are built from something sturdier than old front porches, and time has been gentle to the songs of Lyle Lovett.