During the last 10 years of his life, John Prine underwent a profound reappraisal in Nashville. In 2010, when the first installment of Broken Hearts & Dirty Windows was released, he was a niche influence, beloved by many but still considered something of a cult figure. In 2021, however, he’s the granddaddy of left-of-center country music: a benevolently eccentric artist who deftly blended pathos and humor, as well as a businessman who founded and steered Oh Boy Records, one of the longest-running artist-owned indie labels in Nashville. He located a different kind of success and then scribbled out a roadmap on an Arnold’s napkin for subsequent artists who’d been edged out of the mainstream. Especially with his swan song, 2018’s The Tree of Forgiveness, Nashville finally hailed his artistry, his business acumen, and his determined longevity.

During that same decade, the Americana scene has undergone a tectonic shift, with these two tribute albums serving as fine points against which to measure the change. Vol. 1 featured a dozen acts from various scenes, as though “Americana” extended to the art-country croon of Lambchop, the punk-country DIY of the Avett Brothers and the classic-rock swagger of the Drive-By Truckers. Vol. 2, however, suggests that the roots world has grown narrower, suppressing its twang as well as its eccentricities. Most of these covers, especially on the album’s second side, sound stark, solemn, and very, very serious; they’re missing Prine’s wry sense of humor, his beatific sense of wonder.

Partly that’s down to the song choices. The first volume bypassed some of his best-known songs—“Sam Stone,” “Hello in There,” “Paradise”—in favor of deep cuts and fan favorites, allowing the artists to draw on their personal connections with the catalog. This second volume includes all of those best-known songs, suggesting that this generation of artists must contend with Prine as a public figure. John Paul White’s version of “Sam Stone” somehow sounds even graver than the original, turning it into a funeral rather than a protest. Sturgill Simpson fulfills his ancient destiny by covering “Paradise,” and it sounds exactly like you would expect, no more or less.

Prine’s peers don’t fare much better. The oldest artist here—Emmylou Harris—gets stuck singing about the loneliness of old people on “Hello in There.” She sings beautifully, but the song needs a younger voice to draw out the empathy and compassion. Bonnie Raitt has been singing “Angel From Montgomery” since before Oh Boy hung out its shingle, but her umpteenth version doesn’t find a new angle on the material. On the other hand, Iris DeMent brings a knowing poignancy to “One Red …….

Source: https://pitchfork.com/reviews/albums/various-artists-broken-hearts-and-dirty-windows-songs-of-john-prine-vol-2/