The album was produced by Arif Mardin and features Prine's brother Dave on dobro, banjo, and fiddle while Steve Goodman also contributes on guitar and harmonies.

The material on Diamonds in the Rough strike a musical balance between infectious up-tempo hootenannies and stark, allegorical compositions with recitations that recall Hank Williams' recordings as Luke the Drifter.

They invited me back a week later, and I did it again for an open stage...So about the fifth time I was driving down there I thought, God, the same people are gonna be sitting there.

"[1] Prine admitted to American Songwriter that he borrowed the melody for "The Late John Garfield Blues" from the Jimmie Rodgers song "Treasures Untold", stating "It's a really pretty ballad that he wrote.

The title track, which was originally recorded by the Carter Family, is sung by Prine, his brother Dave, and Goodman without accompaniment.

Regarding "Yes, I Guess They Oughta Name A Drink After You", the John Prine Shrine website quotes the singer: "I was going for a Hank Williams kind of song.

The album opener “Everybody” is a rollicking number about the need for human connection that starts with the narrator bumping into Jesus, who happens to be taking a stroll on the ocean, while “The Torch Singer” and “Rocky Mountain Time” may have reflected the whirlwind changes in Prine's life in the past year.

[2] Village Voice critic Robert Christgau deemed Diamonds in the Rough "Not as rich as the debut, but more artlessly and confidently sung—the gruff monotone avoids melodrama in favor of Prine's own version of good-old-boy..."[4] Critic William Ruhlman of AllMusic opines, "John Prine's second album was a cut below his first, only because the debut was a classic and the follow-up was merely terrific...Diamonds in the Rough demonstrated that Prine had an enduring talent that wasn't exhausted by one great album."

In 1993 David Fricke wrote, "It was, in essence, John Prine-in-the-rough, a superb collection of tunes and tales recorded with acoustic, no-frills living room elegance."

Prine biographer Eddie Huffman observes "Prine had overcome his stiffness in the studio, but the trade-off was vocal control: He came off like a hell-raising redneck...His voice actually cracked here and there, but the surge of energy and good humor more than compensate for the lack of polish.”[5] Record World called the single "Everybody" a "funny funky song by one of America's newest and best singer-songwriters.