Cowboy Poetry & Music Festival stars Tom Russell.

Tom Russell hopes his ambitious forthcoming folk opera/frontier musical The Rose of Roscrea will cast a fresh light on the culture of the cowboy.

Inspired by conversations with his sister-in-law, a former rancher who worked alone on a 3,000-acre Spanish land-grant ranch in California, the singer-songwriter-troubadour has been working on the performance piece for 20 years. (It’s set to be released May 2, 2015.) Unlike the slew of well-known classics set in the West, like Oklahoma and Annie Get Your Gun, Russell aimed to create something with authentic language, history and cowboy songs.

Roscrea delivers 25 new tunes – featuring around 50 guests, including Leadbelly and Johnny Cash, some of whom appear courtesy of old recordings to which Russell secured the rights – and traditional songs. The double album also comes with a book, outlining the history of the songs and performers.

The title track, “The Rose of Roscrea,” is about a 92-year-old guy looking back on a life in which he moved to the West from Ireland in the 1880s as a kid and became a cowboy and an outlaw.

“The backdrop of this musical looks at the bedrock of American folk and cowboy songs,” Russell says, “ and it has to be entertaining, of course.”

Whether it’s the color he scribbles into the slice-of-life prose that lines his 30-plus records, or the color he playfully paints into his impressionist folk art, just about everything Russell creates is also entertaining. For the 16th annual Monterey Cowboy Poetry & Music Festival, he performs 6:45pm Friday and Saturday in downtown Monterey. The Weekly caught up with him two weeks before the show.

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You describe yourself as an outsider. Who are the insiders?

All the writers standing in line in Nashville, anyone putting on a songwriter workshop, the folks hanging out at conventions and alliances – that kind of stuff. Game players. That kind of thinking has led to the demise of songwriting.

How do you approach songwriting?

Head on. I pick up the guitar or sit down at the piano and pound away. Mostly getting nowhere, but I put myself in the position everyday and pray The Muse will throw a few brilliant lines. I paint. Then go back at it the next day. It’s mostly hard work with occasional flashes of illumination and the eternal struggle for a rhyme or idea that isn’t a cliche. Arriving at something that might make a listener pull their car over.

How does criminology affect your art?

On the record Blood and Candle Smoke, I dug up old memories of working as a criminologist in Nigeria, during the Biafran War. I recorded two songs with the band Calexico, “East of Woodstock, West of Viet Nam” (sic), and “Criminology.” I sang the first one on the Letterman TV show a few years ago.

How do you define “American Dream”?

The search for redemption… or oblivion. The idea that in your journey across the final frontier, the long way around might be the shortest way home. I’ve tried to get into that in [The Rose of Roscrea]. In the end, I think people came to America to gain the freedom to do what they wish on their own terms. And they kept moving west to find that. It’s the story of my own family.

Charles Bukowski said, “Some people never go crazy, what truly horrible lives they must live.” What are your greatest moments of craziness?

I had a 20-year writing correspondence with Bukowski, and that was pretty crazy. It’s in the book Tough Company. Africa was crazy. Lots of guns pointed at me. I came of age there. Then, working a few years in Skid Row bars in Vancouver, backing up sword swallowers, topless dancers and female impersonators. That was crazy. Big time crazy. Hanging out with Johnny Cash, meeting Bob Dylan, sneaking in with The Beatles at the Hollywood Bowl 1964.

He also said, “You have to die a few times before you can really live.” Describe a time that you “died.”

I die a little every afternoon, then happy hour revives me. I’m a strong believer in good Chardonnay and great tequila. Within reason. My wife keeps me in line. She’s a Swiss psychologist. You can survive if you have a sense of humor and a built-in bullshit detector.

Talk about having Johnny Cash record your tune “Veteran’s Day.”

We had breakfast in Switzerland when we were on the same show, and he started talking about my songs “Blue Wing” and “Veteran’s Day.” He said he was going to record them, and he did. I was floored. That night, he got me up on stage in front of 10,000 and had me sing “Peace in the Valley” with him. One of the high points of my life in music. He had a huge heart. They don’t make folks like that anymore.

Give me a Tom Russell story the world has never heard.

I shook hands with John F. Kennedy. He asked me where the nearest restroom was.

What’s next?

Going out on the road with this double record. Painting. I also write serious essays on the West for a fine journal called Ranch and Reata.

MONTEREY COWBOY POETRY & MUSIC FESTIVAL 4pm Friday, Nov. 21; 8:45am Saturday, Nov. 22; 9am Sunday, Nov. 23. Monterey Conference Center, 1 Portola Plaza, Monterey. $220/pass; $10-$35/event. www.montereycowboy.org