Remembering John Prine: Eight Covers Of “Angel from Montgomery” You Need To Hear

John Prine’s “Angel from Montgomery” may be a country-folk standard today, but back in 1969, it started as just another “song about old people.”

After the songwriter — then a mailman in Maywood, Illinois — wrote the spellbinding “Hello in There” about the loneliness of senior citizens, his songwriter friend Ed Holstein asked to collaborate with him on another tune in the same lane. But Prine felt he had already spoken his piece on the subject.

“I can’t do that, because I put everything about old people into that one song,” he recalled telling Holstein in an interview with author Nick Spitzer. After Holstein turned down an offer to write a song about a middle-aged woman who feels stretched thin by domestic life, Prine decided to write it himself.

The resulting song, which appears with “Hello in There” on 1971’s John Prine, addresses aging and isolation in first-person. In the ensuing decades, it became a concert staple and fan favorite of the late Prine, who tragically died at 73 of COVID-19 complications on Tuesday (April 7).

“I had this really vivid picture of this woman standing over the dishwater with soap in her hands and just walking away from it all,” Prine explained in Paul Zollo’s 1991 book More Songwriters on Songwriting. “I just let [the song] pour out of the character’s heart.”

And what poured out is no pale imitation of its predecessor, rather, it’s another side of the same coin. And songwriters in its wake from John Denver to Old Crow Medicine Show have taken a stab at this aching modern standard. To mourn Prine’s passing and to pay homage to one of his most enduring songs, here are eight covers of “Angel from Montgomery” we think you should hear.

John Denver, “Angel from Montgomery” (Farewell Andromeda, 1973)

On the heels of his first Top 10 album, 1972’s Rocky Mountain High, Denver released the less-heralded Farewell Andromeda, a grab-bag of originals and covers. His cover of “Angel of Montgomery,” which was well-suited to his flat tenor due to its limited note range, is the standout cut of the set because it doesn’t sound forced. Play it straight, add a little church-aisle piano, and you’re off to the races.


Bonnie Raitt, “Angel from Montgomery” (Streetlights, 1974)

Arguably, the master blues-rocker Raitt released the definitive version of “Angel” on her album Streetlights. “I think that ‘Angel from Montgomery’ probably has meant more to my fans and my body of work than any other song,” she told Performing Songwriter magazine in 2000. “It’s just such a tender way of expressing that sentiment of longing.” Raitt throws herself into “Angel” as the housewife seeking deliverance from a fly-filled kitchen.


Ben Harper and Tom Freund, “Angel from Montgomery” (Pleasure and Pain, 1992)

Pleasure and Pain is a loose, casual vinyl-only album between old friends Ben Harper and Tom Freund. “Any time we collaborate, it feels like we pick up right where we left off,” Harper explained to Americana Highways in 2018. (Freund concurred: “There’s a connection and a language that we’ve always had.”) On their duet of “Angel from Montgomery,” both men croon in loose harmony as if they’re recalling it from memory.


Susan Tedeschi, “Angel from Montgomery” (Just Won’t Burn, 1998)

While Tedeschi is best known for co-leading the Tedeschi Trucks Band with her husband Derek Trucks, her solo discography is worth seeking out. Her second album Just Won’t Burn features a few well-chosen covers, including “Angel from Montgomery.” Similar to Raitt’s famous rendition but dazzling, all the same, her version shows that Prine’s tune is so reliable and accessible that all one has to do is belt it and mean it.


Old Crow Medicine Show, “Angel from Montgomery” (Broken Hearts and Dirty Windows: Songs of John Prine, 2010)

Featuring covers of Prine songs by Americana acts he influenced, like Drive-By Truckers, Bon Iver’s Justin Vernon, and Deer Tick feat. Liz Isenberg, Broken Hearts and Dirty Windows sparked something of a late-period Prine renaissance. Old Crow Medicine Show recast “Angel from Montgomery” as a readymade bluegrass standard that — as far as compelling musicians to go cheek-to-cheek on each available mic — goes toe-to-toe with “The Weight.”


Ani DiFranco, “Angel from Montgomery” (live at Music Hall of Williamsburg, 2011)

The stylistically bubbly singer-songwriter Ani DiFranco performed “Angel from Montgomery” at Music Hall of Williamsburg back in 2011. By fingerpicking the song on tenor guitar and curling Prine’s vocal melody in surprising directions, DiFranco takes an appealing detour to the emotional zone where dreams are lightning and thunder is desire.


Buddy Miller & Friends, “Angel from Montgomery” (feat. Brandi Carlile and the Lone Bellow)(Cayamo Sessions At Sea, 2016)

Recorded on the annual Cayamo Festival Cruise that takes a shipful of music fans through the Caribbean Islands, Cayamo Sessions at Sea — featuring Kacey Musgraves, Richard Thompson, Lucinda Williams, and other luminaries — less captures scripted moments than documented musicians’ hangs. Singer-songwriter Carlile and Brooklyn alt-country band The Lone Bellow join Nashville cat Buddy Miller for this verse-trading take on “Angel.”


Langhorne Slim, “Angel from Montgomery” (live on KEXP, 2018)

Sean Scolnick a.k.a. Langhorne Slim is perhaps Prine’s Generation X analog, with a similar bullhorn vocal range, tight song structures, and sweet guilelessness with a pen. His version of “Angel from Montgomery,” performed on KEXP in 2018, doesn’t spin it in any new directions, but that’s not the point; inhabiting Prine’s “old woman named after [her] mother” is a songwriter’s rite of passage that Scolnick handles with aplomb.


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