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20. Johnny Cash – Sam Stone

One of the bleakest, maybe the bleakest of Prine’s catalog, this grisly tale of an addicted veteran offers a sense of road-weary gravitas. OK, Cash’s acquaintance with substances may have been a little different, not to say managed better, than Stone’s, but he isn’t blind to the potential similarities of outcome. This comes from a 1987 Live in Austin TX show and album; Cash’s band is as sturdy and solid as necessary, his selection of songs a precursor of the sort of material later tackled on his iconic American Recordings. The only letdown is his gaffe as he closes, attributing the song to John Price. Ouch! – Seuras Og

19. Whiskey & Co. – In Spite of Ourselves

With the irreverence and whimsy that is painted all over the original song, “In Spite of Ourselves” seems tailor-made to be covered by a cowpunk band. The band Whiskey & Co. fits the bill quite nicely. There is a certain looseness here that separates this version from the song’s original incarnation. Our heroes that sing back and forth to one another seem to be coming from a much darker place, more Kurt and Courtney than Ozzie and Harriet. – Walt Falconer

18. Those Darlins – Let’s Talk Dirty in Hawaiian

The Broken Windows tribute album featured bigger names, several of which appear on our list: Old Crow Medicine Show, My Morning Jacket, The Avett Brothers, etc. Those Darlins was not the headline act here, and they picked a relatively obscure song too. But the band, a Nashville trio who toured with the likes of JEFF the Brotherhood and Dan Auerbach before breaking up a few years back, nail the fun and silliness. If “Sam Stone” got you down, this will pick you right back up. – Ray Padgett

17. Emmy the Great ft. Lightspeed Champion – Christmas in Prison

According to Prine, this song isn’t actually about Christmas in an actual prison, but instead, “about a person being somewhere like a prison, in a situation they don’t want to be in. And wishing they were somewhere else. But I used all the imagery as if it were an actual prison, with the lights swinging around the yard, the food tasting bad, making guns out of wood or soap. And being a sentimental guy, I put it at Christmas.” This version, recorded for the 2006 compilation album It’s Not Like Christmas, features Emmy the Great (real name, Emma-Lee Moss) and Lightspeed Champion (real name, Devonté Hynes). They began working together when Hynes was recording his debut album in Nebraska, with Mike Mogis and the Saddle Creek/Bright Eyes group of musicians. Like the original, it is mellow and contemplative, but Emmy’s less gruff vocals, and the violin and keyboards, give it a different, more atmospheric feel. – Jordan Becker

16. Jason Isbell & the 500 Unit – Storm Windows

Jason Isbell’s love and admiration for Prine runs deep. He not only covered innumerable Prine songs over the years and performed with the man himself, but, along with his wife and fellow musician Amanda Shires he grew to be a dear and trusted friend. Isbell wrote an incredibly moving remembrance of Prine upon his passing, within which was an especially touching, tearjerking anecdote: “When I was a baby, my 17-year-old mother would lay me on a quilt on the floor of our trailer in Alabama and play John Prine albums on the stereo.” Isbell’s reverence and emotional understanding of Prine’s songs shines through on his handsome version of the title track from Prine’s 1980 album Storm Windows, which Isbell originally released as part of a special Record Store Day live EP in 2017. While the original sounds like some glorious fantasy scenario where Prine is fronting The Band, Isbell and his band 400 Unit takes a more languid, laid back approach, capturing its blurry, nighttime fever dream to perfection. – Hope Silverman

15. Bob Dylan – People Putting People Down

One summer evening in 1971, John Prine was sitting in Carly Simon’s apartment with fellow songwriters Kris Kristofferson and Steve Goodman, when there was a knock at the door. It was Bob Dylan. “You could have sent a Martian down and it wouldn’t have surprised us as much as seeing Bob Dylan,” recalled Prine during a 2019 interview on the Alamo Jones Show. His shock doubled when it emerged that Dylan had already acquired an advance copy of Prine’s debut album, which was still weeks away from release. “I know all your songs, but how do you know mine?” said the incredulous Prine as Dylan began singing a tune from the upcoming album.

Dylan may have known John Prine’s songs, but to date he has only covered one: “People Putting People Down” from Aimless Love, during a performance in Rome on June 6, 1991. This year was a strange one for Dylan, in which he often seemed disillusioned and disconnected from his own songs. However, even the most disastrous concerts often featured moments where Dylan would suddenly come to life, and deliver a song with total command and feeling. This performance is one of those moments, and Bob sings Prine’s lyrics with the authority of someone who has lived every word. – Tim Edgeworth

14. Erin Harpe and the Delta Swingers – Angel from Montgomery

This version, from Erin Harpe and the Delta Swingers, was included my Five Good Covers piece on “Angel from Montgomery,” but if we were doing “Good, Better, Best,” it couldn’t win “Best,” because that’s reserved for Bonnie Raitt. Harpe, originally from Maryland but now based in Boston, and her band the Delta Swingers play fun, upbeat danceable blues, highlighted by Harpe’s fingerpicking and soulful voice. While most renditions of “Angel” focus on the subject’s sadness, it seems like this one looks more toward the hope that she might have a better future. Or maybe this band just can’t help themselves from turning any song into a good-time stomp. – Jordan Becker

13. My Morning Jacket – All the Best

Another one off the Broken Windows tribute that supplied a few songs here (this won’t be the last). Though largely a swooning country ballad, Jim James incorporates an omnichord, a funny-looking early-’80s handheld synth he was using at that time. That’s that sort of digital shimmer you hear. You can watch him playing it on one of his own songs here. – Ray Padfgett

12. Tammy Wynette – Unwed Fathers

Released in 1984, the song “Unwed Fathers” was considered by some at the time to be the best John Prine song since “Sam Stone.” The genesis of the song came from two separate songs that were under construction: “Children Having Children” and “Unwed Fathers.” Morphing the two into one song, “Unwed Fathers” was the last title standing. Hearing a female voice on the song was not foreign to the ear, since Prine’s then-wife Rachel Peer-Prine sang a few verses on the original, but in the capable hands of Tammy Wynette, the song is carried into next-level greatness. Hearing the story from the perspective of a woman sitting alone in the Greyhound station, going from teenage lover to unwed mother, it is hard to separate the singer from the song. – Walt Falconer

11. Adrianne Lenker – Summer’s End

Several days before Prine’s passing, Adrianne Lenker of rootsy indie band Big Thief covered a latter-day Prine classic, the elegiac “Summer’s End.” Her version is positively gripping, with the frailty and emotion in Lenker’s voice perfectly conveying the song’s powerful embrace. Both Prine’s and Lenker’s versions are absolute tearjerkers, but their innate warmth makes it feel good to just let go and let them flow. – Hope Silverman

The list finishes on Page 4.

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  7 Responses to “The Best John Prine Covers Ever”

Comments (7)
  1. Eddi Reader’s version of ‘Hello In There’ is really great, I think.

  2. Listened to all John prine songs luv them all

  3. Are you collecting John Prine covers from not so well known artists for a future post?

  4. That disappoints that Johnny Cash didn’t know John Prine. If you are gonna borrow someone’s art you really should know credit with authenticity. Also Phil King– obscure music man strikes again! There are some not prime time players in the first 3 installments/pages of this series. Cmon srsly there are no Taylor Swifts or Eddie Vedders here! I’m sure Youtube is full of unsigned folks covering Prine songs.

    • Hi I like to put together music collections (I make no money off of it share it with a few friends). I am working on a collection honoring John Prine, his buddy Steve Goodman, and Michael Smith. So I am researching covers too as part of this endeavor. I came across a clip of John being interviewed the other day, and he spoke about Johnny Cash’s cover of Sam Stone. Johnny had a conversation with John P., and indicated that he loved the song. But that he was troubled by the line “Jesus Christ died for nothing I suppose,” and John P. responded politely that the line was really the core of the song. But John also said to the interviewer, “hey it was Johnny Cash,” suggesting that he was not going to push it with Johnny because Johnny was, well, Johnny Cash. If you listen to the cover, Johnny did change that line, and though I respect Johnny’s religious leanings, really I agree with John P. that the line about Jesus just demonstrates the hopelessness of Sam Stone’s state of mind and his entire being. The line is really kind of essential. So Johnny did have some interaction with John P. about the song, and likely about more than that, and it is somewhat unfortunate that Johnny incorrectly stated John’s last name at the end of the cover. Not defending Johnny Cash, but I think it was just an honest mistake.

      • Cash knew him. He shared once that he listened to Prine when he needed inspiration. It may have been a slip of the tongue. I’m sure Cash felt badly later.

  5. You missed out on Jeffrey Foucault. He recorded an entire (brilliant) album of all Prine covers called Shoot The Moon Right Between The Eyes.

    It’s a beauty… Highlights include the most heartbreaking Mexican Home… A stunning One Red Rose… And a superb That’s The Way That The World Goes Round.

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