By the time Guy Clark joined Lyle Lovett, John Hiatt, and Joe Ely on the “Songwriters Tour” in the early 2000s, he had earned a reputation as one of the finest country songwriters of his generation. And although as a singer Clark was the least famous of the four, his solo turns during those shows often made the deepest impression.

Clark died in May at age 74, nearly four years after the death of his long-time wife, and his occasional songwriting partner, Susanna. “Susanna, oh Susanna,” he’d sung on his 1999 album Cold Dog Soup, “when it comes my time, / please bury me south of that Red River line.” If her time’s coming before his took the wind out of his sails, it also gave him one last breath of inspiration. The Susanna-revering title track of his final album, 2013’s My Favorite Picture of You, is almost unbearably poignant.

Clark left behind a body of almost unbearably poignant work. In songs such as “The Cape,” “The Randall Knife,” “L.A. Freeway,” and “The Guitar,” he set wise words to spare, folky melodies that together cut to the emotional quick. “Like a Coat from the Cold” might’ve even been where that master borrower Bob Dylan got the melody for “Is Your Love in Vain?”

Clark was a late bloomer. He didn’t release his first album, 1975’s Old No. 1, until he was 33. His singing bloomed even later. Not for nothing was The Dirt Band’s 1980 version of Rodney Crowell’s “An American Dream” a hit and not Clark’s circa 1978 version.

Not until his 1980s albums Better Days and Old Friends did the sawdust rasp of his voice take on a heft appropriate to the weight of his subjects. Clark had a way of making his favorite topics—whether boats, love, or the numerous characters unique to his native Texas—seem archetypal.

His most favorite topic was food, which he celebrated in “Homegrown Tomatoes,” “Watermelon Dream,” and “Texas Cookin’.” In “Cornmeal Waltz,” he even danced on it.

Uncommonly for country songwriters, Clark tended to avoid gospel references. An exception was Cold Dog Soup’s “Water Under the Bridge.” It begins with the narrator’s remembering his baptism “down at the river’s edge” and declaring that “[a]ll my sins are washed away.”

If anything makes bearable the poignancy of his passing, it’s the possibility that that narrator was Clark.

Four old friends

In 1985, The Highwaymen—Willie Nelson, Waylon Jennings, Kris Kristofferson, and Johnny Cash—covered Guy Clark’s “Desperadoes Waiting for a Train” and released it as the second single from their eponymous debut album. That song and 15 others comprise Sony Legacy’s just-released The Very Best of The Highwaymen.

It differs from The Essential Highwaymen (Sony’s 36-track, 2010 Highwaymen compilation) by including renditions of Rivers Rutherford’s “America Remains,” Paul Kennerley’s “Welfare Line,” Bob Seger’s “Against the Wind,” and Bob Dylan’s “One Too Many Mornings.” It also includes two live cuts, “City of New Orleans” and “The King Is Gone (So Are You),” that sound more at home on Sony’s other just-released Highwaymen album, Live: American Outlaws.

A three-CD, one-DVD package assembled from several shows, American Outlaws preserves for the ages the ebullient bonhomie of four good friends luxuriating in the privilege of deploying their multiple solo and not-so-solo hits one after the other before equally ebullient crowds.

“Is everybody having a good time so far?” asks Jennings at one point. “You might as well. We done got all your money.” The reaction he gets suggests the audience considered its money well spent. —A.O.