Editor’s Note 7/23/19: John Prine’s team announced he is postponing the remainder of his summer concert series due to health issues. The Red Rocks show with the Colorado Symphony has been rescheduled for September 18. 

John Prine is known for his wit, rambling-yet-pointed stories, and tell-all cultural criticism. The celebrated singer-songwriter has won two Grammys and last month was inducted to the Songwriters Hall of Fame, but Prine’s own notoriety isn’t so important—what matters is the imprint he’s made on American music.

Since the early 1970s, when the mailman-turned-folk singer was discovered by legends like Roger Ebert and Kris Kristofferson, Prine has put out 21 albums, launched his own label, and had his songs recorded by the likes of Johnny Cash (“Sam Stone”), Bette Midler (“Hello in There”), Bonnie Raitt (“Angel from Montgomery”), Zac Brown Band (“All the Best”), Miranda Lambert (“That’s the Way the World Goes Round”), and George Strait (“I Just Want to Dance with You”).

Prine’s music is often melancholy, but it isn’t without hope. Diagnosed with squamous cell cancer in his neck in 1998, Prine underwent surgery and radiation treatment before releasing an album of duets, In Spite of Ourselves, a year later. His voice had changed, turned lower, deeper, and, in his words, “friendlier.” In 2016, he released another album of duets titled For Better, Or Worse, with the likes of Kacey Musgraves and Amanda Shires, a testament to his influence across generations. Last year came the critically acclaimed The Tree of Forgiveness, an album of originals (his first in 13 years) produced by Nashville Americana legend Dave Cobb, with guest appearances by Jason Isbell and Brandi Carlile. At 72 years old, Prine’s perhaps more popular than he’s ever been.

On July 28, Prine will perform with 65 members of the Colorado Symphony at Red Rocks Amphitheatre (the full orchestra is 80 full-time members, but Prine has his own band), in what promises to be a highlight in a 50-year career. I’m With Her—a group made up of Sara Watkins, Sarah Jarosz, and Aoife O’Donovan—will open. In anticipation of that show, we sat down with Anthony Pierce, chief artistic officer for the Colorado Symphony, the man whose job it is to make these types of shows happen.

5280: How did this collaboration between John Prine and the Colorado Symphony come about?
Anthony Pierce: You know, John Prine is a living legend, obviously—a very special artist. This is the guy who wrote “Angel from Montgomery.” He played the Buell Theater last year and we’d already started the conversation. We asked if [playing with the Symphony] was something Prine would be interested in doing, and he thought about it for some time. It can be an intimidating proposition for some people if they’re not from the orchestra world. His team came back and said, “We love it. Let’s do it and build a beautiful show and make it a very special evening at Red Rocks.” And it’s going to be.

Once he said yes, what came next?
I connected with Prine’s music director, a guy named Jason Wilber, who’s been [the guitarist in] his band for years and years. We talked about what the instrumentation was, how many people are in the orchestra, are we going to have adequate rehearsal time? All those things are conversations that have to happen to make an artist comfortable. Chris Dragon is conducting this one, who is our resident conductor.

Is there any opportunity to rehearse together beforehand?
We’re loading into Boettcher [Concert Hall] and bringing everyone in to rehearse on July 27, the day before. We really just have one day to rehearse, so the orchestra has to show up prepared. Everybody’s a pro and it’s Chris Dragon who’s got to hold it all together. He’s already been studying the scores for weeks—he’s the one who has to keep the train on the rails.

So the setlist has been nailed down for months?
Yeah, I’ve got the setlist, it’s beautiful. It’s going to span Prine’s whole career. I talked to Fiona, who’s his wife and manager, early on, and I also talked to Jason Wilber early on, and one of the things they told me was what John said: “This has to be a John Prine show.” What he meant by that was that he has to deliver what his [fans] expect from his show. He didn’t want to have it suddenly be a different thing. He wanted it to be an expanded, more unique thing for his people. At least that’s how I interpreted what he meant.

It’s hard for me to imagine Prine’s music with a full orchestra.
You think it’s hard to imagine it? I think it really works. Look at Gregory Alan Isakov [who the symphony played with in 2017], he’s a folky singer-songwriter and the nature of that genre is that there’s a lot of space that can be filled. You want to make sure it’s filled tastefully, but the space is there. So that’s the challenge. I think Prine’s music lends itself well to orchestration. And John’s still going to play some solo stuff during the set.

The Symphony is playing with Tenacious D just two nights before—what’s the drive behind these varied collaborations?
It’s a fun process and we’re lucky. We’ve worked hard to build a reputation as an orchestra that does this well. These people trust us to help build these shows, and a lot of orchestras have followed suit. We don’t want the orchestra to be a backing entity, we want the orchestra to be a very prominent, value-added part of what any band already does. A band typically does their show without an orchestra, but we have an internal goal of making them only ever want to play with an orchestra.

Is that the Symphony’s larger mission?
We’re about putting on great shows, that’s our main focus, as well as exposing people to what live, symphonic music can be. For some people, these shows are their first exposure to what live symphonic music can be. That’s our charge: We’re curators of a classical art form and we’ve got to ensure everybody experiences it.

If You Go: John Prine and the Colorado Symphony will perform together July 28 at 7 p.m at Red Rocks Amphitheatre. Tickets start at $55