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Up Close & Personal with John Prine and Sturgill Simpson


By Chris Isom with photos by Adrienne Cohen Isom

We’ve come to expect good things from the GRAMMY Museum and their GRAMMY Pro exclusive Up Close & Personal series raised the bar. Spending the evening with American country/roots singer/songwriters John Prine and Sturgill Simpson, talking creative process and telling stories moderated by music journalist Paul Zollo, proved a rare treat for the handful who attended.

Prine, a legend among singer songwriters, has been called a songwriter’s songwriter. His songs have been covered by, Johnny Cash, Bonnie Raitt, the Everly Brothers, John Denver, Kris Kristofferson and many others, and is largely recognized as a continual inspiration to young and old songwriters alike. The late great Johnny Cash is famously quoted as saying, “I don’t listen to music much at the farm, unless I’m going into songwriting mode and looking for inspiration. Then I’ll put on something by the writers I’ve admired and used for years–Rodney Crowell, John Prine, Guy Clark, and the late Steve Goodman are my Big Four.”

Sturgill Simpson, whose 2016 record A Sailor’s Guide to Earth, hit No.1 on the Country Album chart and No. 3 on the Billboard 200, coming off the heels of his GRAMMY nominated breakout record Metamodern Sounds in Country Music, is considered one of the newest and most important voices in americana today.

Paul Zollo, who moderated the interview, is a renowned author and music journalist, he is best known for his bestselling book  Songwriters On Songwriting which has been called “the songwriter’s bible” and includes interviews with Bob Dylan, Paul Simon, Randy Newman, Laura Nyro, Pete Seeger, Leonard Cohen, Neil Young and Frank Zappa among others.


Zollo kicked off the night asking Prine how he got his start in music. Prine related stories of his early youth playing bluegrass with his brother explaining how he first began playing accompanying guitar while his brother was learning to fiddle.

“You have to practice violin with someone who loves you, and I loved my brother so i’m glad he taught me, I don’t know if I would’ve stuck with guitar playing but he taught me how to play because he needed someone to play the rhythm for him, and I just took off from there. I was mainly interested in rock n roll but since i grew up on old timey music and bluegrass then that’s the first kind of melodies I wrote, because that’s the only kind I knew on guitar,” tells Prine.

Zollo and Prine went on to discuss the importance of early rock ‘n roll on Prine’s songwriting. In particular Chuck Berry, as Prine beamed, “His stuff (Berry’s) you could tell what the melody was like by just reading the words, the melody would just jump off the page.”

Steve Goodman was an important player in Prine’s early career and is credited with introducing Kris Kristoferson to Prine. Kristoferson was instrumental in getting Prine noticed by the music world at the time. As, Prine tells, “we had our little suitcases and guitars, we get out of a cab and there’s Kris and his whole band, you couldn’t drink in the bitter end, you’d go next door to a place called The Dugout, they just served ice cream in the bitter end, I saw Stevie Wonder eatin a banana split one time at the bitter end.”


Sturgill’s timing throughout the interview was brilliant, he was humble and funny as hell and clearly has the kind of admiration for Prine all fans do. Seeing Sturgill in this context was revealing and seemed to confirm a lot of reports we hear about him as a humble character. He described his first foray into Nashville in his mid twenties as an aspiring songwriter as a basic failure, “I did meet a few mainstays, some older guys I learned from that’d been around and kinda chewed up and spit out and had that sustained bitterness from it and I just realized I didn’t want to end up like that so I took that railroad job.”

However, Sturgill describes coming back older wiser and more firmly rooted in his life and his craft, “when I came back, sorta knowing all that, I realized I needed help or at least somebody to sit down and talk to and just say, well where do you start and how does somebody do that.”

Sturgill described the importance of having a manager who knew how to say no to false opportunities in Nashville but with whose help after two years of kicking around the town he was able to land a deal with Jonathan Levine, head of paradigm booking agency. Subsequently, after putting out his first two records independently, and now with Atlantic records. Sturgill has just released his follow up to “Metamodern,” A Sailor’s Guide to Earth. Sturgill stressed the role of touring in the writing and development of most of the songs on Metamodern sounds of Country Music.

Zollo asked, “So you wrote all those songs while you were touring?”

“Most of em yeah, they were tested and arranged, and I had em formulated, we’d carved the band out, they were all young very raw talented dudes, so when we went into the studio for metamodern we had a very short conversation about sonics and then once the mics were set up nothing really moved and we just banged em all out, so that was like capturing that moment of that band in a raw setting like that, just live, as we would a show,” said Sturgill.


Listening to Prine relate these stories is almost as entertaining as one of his songs, there is a similar meter and flair for the obtuse and whimsical elements of life. These types of real life observations interjected amidst seemingly unrelated life events are one of the defining aspects not only of Prine’s speaking style but of his lyrics as well.

Prine also first met Bob Dylan on this trip, who, unbeknownst to Prine was already a fan due to a demo Jerry Wexler had sent him. “When I performed a few weeks later (in New York), he got up and played harmonica and sang with me, I introduced him I said, Ladies and gentleman Bob Dylan! About three people in the club clapped, they figured I’m this joker guy,” deadpans Prine.

Prine’s humble character and humility make him a uniquely empathic character. Zollo also quoted Dylan who described Prine’s music as “mid western mind trips to the nth degree.”

Prine talked about being a mailman in a suburb of Chicago as having informed much of his early writing and development, Prine says, “I always compared it to being in a library with no books. It was quite a long time to have to yourself. But you had nothing but your imagination to read ya know.”

Zollo mused, “and would the song start while you were delivering the mail?” Prompting Prine, “Well somebody would say something, a little something would catch my ear, and well i’d take that and say it over and over, all of the sudden i’d wonder what kind of a character would say that, what they’d come out of, I was doing it purely to entertain myself. You know, to get through that long day, to get to the end of the mail route.”

When asked how he is able to wed the serious and the humorous on songs like “Sabu” and “Sam Stone” and pressed to explain his craft in detail, Prine laughs, “I could go in before a judge anywhere and just go, dang, I didn’t know what I was doing. Hell, I was trying to play in a goda de vida.”

Sturgill adding, “Please tell me that’s true.”


Both Prine and Sturgill served in the Armed forces and have been shaped by the experience although under vastly different circumstances. Prine was drafted during the Vietnam era but ended up being sent to East Germany for which he said, “I’m still dancing.” Sturgill was in the navy and and did not see active combat although they both related to dealing with the experience in similar ways.

Prine saying, “A lot of my buddies ended up in Vietnam and they came home but none of em were ever the same people, regardless of whether they were in combat or any where near it, it’s just if you’re over there and goin day after day with nothing happenin’ and then you could go get a beer with a buddy and he’d step on a mine. Your training to go into the military is so intense to take your individuality away from you and then they leave ya hangin’ like that when you get out, you still think you’re supposed to jump when the siren goes off and stuff.”

On his experience, Sturgill said “we weren’t even at war and it was pretty much the same thing, they get you wound up tighter than a banjo string and then most of it hurry up and wait and everybody was on drugs and even now they don’t talk about it, these guys coming back it’s rampant and you don’t see it on the news, there’s a lot of drug abuse in the military and especially guys getting out of the military with no one to talk to or how to deal with it, it’s the same old thing.”

“Sam Stone,” the heart wrenching story of a disabled Vietnam vet who returns from the war with shrapnel in his knee, and a heroin addiction who ends up taking his life, is a timeless John Prine song as relevant now as during the Vietnam era.

The wit and candor of these two americana stalwarts engaged in a serious interview with the author of “Songwriters on songwriting” about songwriting should not be underestimated. Both Prine and Simpson come across as having been fairly relatable “cut ups” at some point in their life, both of these guys are incredibly poetic but don’t take themselves too seriously, unlike so many pop artists today, both of these artists wed the light with the dark, the serious with the whimsical, and the profound with the mundane. There was as much heartfelt laughter as there were poignant insights into the creative process and the tortured soul of the artist. Zollo, pressing Simpson as to why George Harrison was his favorite Beatle.

“Ah, a lot of reasons, I think more what he came to realize music was for in terms of his life, even, somebody that reaches that level of success and kind of keep themselves on a focused plain of expression, I always thought that was really cool, and not get kinda hung up in the idea of oneself, whereas, Paul and John… maybe, maybe might have? (pause)  At times?” (big laughs from crowd), said Sturgill.

The chemistry between Prine and Simpson was great and in no small part Zollo’s guiding hand on the rudder of the interview.  Zollo clearly has a great talent for culling meaningful insights from songwriters. Prine and Simpson both professed to have written most of their most popular songs in a single sitting and to have merely been “the stenographer,” However, as uncomfortable as it made them, Zollo repeatedly pressed them to talk about their “craft” maybe more than either one wanted to fully explore. Perhaps one of the most interesting segments of the interview was spent exploring this dynamic of writing a song all in one go or returning to an idea and developing it over time. Sturgill conceded that he had not as of yet engaged in co-writing but rather written all his songs himself. Prine has engaged in co-writing and, ironically, one of his famous co-writing endeavors with Goodman for which he did not take writing credit because they wrote it as a song “making fun of cliches in country music” was the number one hit country song “You never even called me by my name,” covered by David Allen Coe.

Prine expressed the opinion that it was easier to come back to some song you may be co-writing with someone because you can have a conversation about it. If earlier you were seeing the story going in two different directions, you may be still able to come back to it and figure out an ending you both agree on, however, that luxury is not afforded you when you are working on a song yourself.

With Zollo inquiring, “But so many great songs were the result of a lot of work and coming back to them, all the great ones didn’t come fast did they?” Prine said, “It’s easier for two co-writers to go back together and figure out ok, now they can kind of have a conversation about it and figure out, ok what do we need here, but when I write alone I can’t have that conversation, I gotta go wherever the song came from, I gotta follow it, and I have to decide whether i wanna take ownership.”

“And sing it for the rest of your life,” a monotone Sturgill chimed in to the audience’s delight.

Prine adding, ”I know, that’s my piece of advice for songwriters, make sure you like the song you wrote, it might be a hit.”

grammymuseum.org  |  fb  |  video (of the show)  |  sturgillsimpson.com  |  johnprine.net

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