Guy Clark: 12 Essential Songs

That the Highwaymen — country music’s most super-sized supergroup — would release this song as their second single speaks volumes about “Desperadoes Waiting on a Train,” which Clark wrote about a Gulf Oil employee who used to rent a room at his grandmother’s hotel. The verses read like vignettes, each one shining a light on an unlikely friendship between a boy and an aging, larger-than-life Texan. By the end, the boy is all grown up and the man is dead, having caught a ride on that train bound for somewhere else.

Clark lost his wife Susanna in 2012, after a battle with lung cancer. The two had become the center of Nashville's folk-country songwriting scene in the Seventies, existing as the social hub for a universe that included Townes Van Zandt, Steve Earle and Rodney Crowell. But Susanna didn't always love the raucous parties that came with such a role, and one day she was standing outside, pissed off that her husband and Van Zandt were once again stumbling around drunk. Someone snapped a picture, and over 30 years later it became the inspiration for "My Favorite Picture of You," off the album of the same title (it would also be Clark's last). That Clark preferred a photograph where his beloved wife looked pretty, yet peeved, says everything about how he understood humanity – as full of humor, sadness and delightful imperfections. "A curse on your lips, but all I can see is beautiful," he sang to a Tejano-tinged chug of the guitar.

There are few songwriters in existence who can sing about something as simple as bacon, lettuce and tomatoes and make it sound truly poignant, not silly — and, certainly, Guy Clark was one of them. Off of his fifth studio album, Better Days, “Homegrown Tomatoes” is a sweet and simple tribute to life’s quieter moments, and to the things often lost in an increasingly fast-paced world. It was also one of the few self-recorded Clark songs to make any chart impact, and was later covered by John Denver on his 1988 LP Higher Ground. “Only two things that money can’t buy,” he sang, “that’s true love and homegrown tomatoes.” As usual, he was right.

Before finally settling in Nashville, Clark briefly lived in Los Angeles, where he pursued a publishing deal and worked at a local dobro factory. But the Texas native didn’t exactly like the lure of Hollywood – the long hours on the highway weren’t feeding his soul, and one day while on the road back from a gig in San Diego, a thought popped into his head. “If I can just get off of this L.A Freeway without getting killed or caught,” he thought, realizing the power of the line and quickly jotting it down on the back of a burger sack with his wife Susanna’s eyebrow pencil. The note became the basis for “L.A. Freeway,” the second song on his debut LP Old No. 1. Opening with a simple strum soon met with a wistful fiddle, it was not only a tune about leaving California but the restless spirit of anyone who feels the crush of a reality they often dream about escaping.

A restless woman hits the highway in this ballad from Clark’s Old No. 1. There’s no motivation or destination mentioned, just a need to get the hell out of dodge. Emmylou Harris sings harmonies on the song’s original recording, which hit stores the same year as her own career-launcher, Pieces of the Sky. What’s most striking about “She Ain’t Goin’ Nowhere,” though, isn’t the personnel as much as the strength of Clark’s hitchhiker, a determined deserter who’s smart enough to avoid the dangers of the road. “She had a way of her own,” Clark sings by way of warning, “like prisoners have a way with a file.”

What is that “old time feeling” of the title, exactly? Clark doesn’t give any easy answers, but teases out the sensation with a series of breathtaking couplets. “And that old time feeling goes sneakin’ down the hall / like an old gray cat in winter, keepin’ close to the wall,” and then, later, it’s circling the block “like old women with no children, holdin’ hands with the clock.” Originally released on Clark’s influential Old No. 1 album, “That Old Time Feeling” waltzes through four-and-a-half taut verses (with Emmylou Harris adding the occasional harmony) describing mortality and loss, and the inevitability of both of those things — not as literal scenes of death, but of their specters hovering nearby.

It’s easy for outsiders to romanticize the poet’s life, but Clark knew from experience that living it was a different story. You could have all the brilliant and legendary friends in the world — and a talent to rival theirs — but you still might not be able to pay the rent in any given month. “Cold Dog Soup” was released in 1999, decades into Clark’s life of poetry and song, and by that time he had come to terms with his lot in life — but that didn’t make it any easier. Playful and catchier than many of his best-known songs, “Cold Dog Soup” references fellow travelers like Tom Waits and Clark’s mercurial friend Townes Van Zandt, as well as literary figures like Alan Ginsburg and Jack Kerouac. They all shared a passion for expression and individuality, and a shared struggle. Clark’s chorus is so tight it feels written in stone, a half-warning embedded in a joke to be passed down and ignored for generations of poets to come. “Ain’t no money in poetry / That’s what sets the poet free / I’ve had all the freedom I can stand. Cold dog soup and rainbow pie / Is all it takes to get me by / Fool my belly till the day I die / Cold dog soup and rainbow pie.”

Clark’s father was a lawyer, but he was a complex man: he fought in World War II, and long held on to the knife that his own mother had given him before he went off to battle. (Clark once joked that is was a Texas rite of passage to receive a “pocket knife and a wet stone” as a child.) Originally released on 1983’s Better Days, “Randall Knife” is about the true layers in which a death washes over us: the memories we attach to simple objects, the doubts we place on our own grief and the emotions that keep creeping in when we least expect them. “They asked me what I wanted, not the law books, not the watch,” he sang. “I need the things he’s haunted.” Clark understood where real value truly resided.

“I got an old blue shirt and it suits me just fine,” the perpetually denim-clad Clark sang on this track off his 1995 album Dublin Blues. By the Nineties, Clark had well-established himself as a quiet, mythological force on the Nashville songwriting scene – never achieving massive fame but seeing his work cut by others who, thanks to flashier personalities or bigger machines, could take them to the charts. But he was respected and adored by many, and proved that he knew what really mattered in life with songs like “Stuff That Works,” an ode to how holding on to our simplest, defining pleasures is more vital than collecting shinier, newer things: “the kind of stuff you don’t hang up on a wall.” Like a great love, a good pair of boots and a brilliant tune.

A songwriter’s work is rarely ever finished, and with a literary mind like Clark’s, the songs become a vivid journey to some other place and time — often a crystal-clear glimpse of the world through someone else’s eyes. “Boats to Build,” from the 1992 album of the same name, hits on the idea of the songwriter as restless creator of those musical vessels. “Sails are just like wings / The wind can make ’em sing / songs of life, songs of hope / songs to keep your dreams afloat,” he sings over soft acoustic guitars, but makes a point to acknowledge the hard work and sweat that goes into converting those raw materials to something tangible — the vehicle for truth that can “sail into the light of day.” Appropriately, seafaring poet Jimmy Buffett recorded his own version of “Boats” for his 2004 album License to Chill.

Clark’s second Warner Bros. LP, The South Coast of Texas, released in 1981, was a thoroughly engaging flirtation with musical styles from folk and Western swing to bluegrass. It also produced Clark’s sole country Top 40 hit as an artist, “The Partner Nobody Chose,” and “She’s Crazy for Leavin’,” a late-Eighties Number One (and co-write) for album producer Rodney Crowell. In 1980, Crowell was the first to record the album’s “Heartbroke,” but it was Ricky Skaggs’ swingin’ version that topped the charts. Both Skaggs’ take on the song and George Strait’s contemporaneous exploration in 1982 on Strait From the Heart offered a radio-friendly reading of the line “pride is a bitch and a bore when you’re lonely” — in Strait’s case, he changed “bitch” to “drag.” But the emotional weight of Clark’s lyric still rang clear.

It’s not the bullet that puts the titular gunslinger in his grave in this stark ballad, but, almost anachronistically, a car. The tale of an old cowboy who can’t forget the smell of the black powder or the “son of a bitch” into whom he empties his gun, the song was cut by Johnny Cash as the title track to his 1977 album. Over the course of a sprawling narrative, he remembers standing his ground in a dusty street that’s now paved and overrun by traffic — which ultimately causes his demise. But Clark’s lyrics, as in “Desperados Waiting for a Train,” are, on a deeper level, more about the cruel passage of time than some superficial hit-and-run. For his own version, on 1976’s Texas Cookin’, Clark enlisted the era’s alpha outlaw for harmony vocals: Waylon Jennings.