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Hang out with The Highwaymen via Matt York’s ‘Songs & Stories’ at City Winery Boston

The 2022 Boston Music Award nominee for Best Country Artist presents a musical history of the country supergroup.

Matt York. Handout

Pembroke native Matt York has been quietly amassing an impressive resume of original music for years — his moody country rock with a jangly edge has instantaneous appeal, combining wry lyrics about barflies, addicts, ex-lovers, and fading summers with infectious melodies and a rocker’s penchant for strumming his way through heartbreak. 

He has a new disc out, “Gently Used,” that fits right into his pantheon: His fifth album, it’s full of rambunctious country stompers like the opening track “If You Want Love” and poignant not-quite-love songs like the sweet, sad “Without You.” So with a track record like that to draw from, what’s Matt York doing going around singing songs by — and telling stories about — outlaw country’s Mt. Rushmore? Specifically, The Highwaymen, the supergroup comprising Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson that released three albums between 1985 and 1995.


“When I was traveling down through Texas and Tennessee playing gigs before COVID, it seemed like Willie and Johnny Cash were omnipresent,” York recently told “But I felt like Waylon, Kris, and some of their counterparts like Merle Haggard and Ray Price were being forgotten over time. All of those guys have had a profound influence on my own music. 

“I’d lost my longtime day job during COVID and started doing this at libraries, churches, and any other place that would have me,” York explained of his current show, which combines interpretations of The Highwaymen’s music and stories about their lives. “Through word of mouth, it just seemed to keep growing and it was clear that it was resonating with people, so I just kept going with it.”

In advance of York’s Highwaymen “Songs & Stories” show at City Winery’s Haymarket Lounge Nov. 20, he talked to about his unexpected career turn, and what’s next for his new music.

Some responses may have been edited for length and clarity. What can Boston audiences expect from the Songs & Stories show?


Matt York: I’m excited to perform at CW. I’m going to have some special guests join me for some songs. I think the biggest thing I’d impress upon people is that I’m not impersonating these guys, I don’t just play their biggest hit songs. I try to blend interesting and at times humorous stories about these guys’ careers with stripped-down versions of their songs. It’s a one-man show for the most part. I never do the same set of songs twice, and I never tell the same set of stories, so if people have seen me do this somewhere else, I promise this will be different. 

I just picked up my car from the mechanic, and I’ve driven 10,000 miles in two months. I’ve done 100 gigs since Memorial Day, so I spend a lot of time driving and listening to music. I try to touch on as many aspects of their lives as I can jam in. 

These men were superheroes to many, but each was also deeply flawed at points in their lives. Each battled drug/alcohol problems, each had complicated relationships with religion. Three of the four served in the military, and all four of them were mega-stars, so there’s a lot to cover.


Some supergroups work better than others, but The Highwaymen has to be one of the most successful. Besides the individual talents involved, what do you think makes them so compelling as a group?

I remember Marty Stuart said that The Highwaymen were American music for a lot of people. They weren’t just country songs, they were songs and artists that transcend genre. When I do these concerts, the ages of attendees are all over the place, but people of all ages love these songs and the men that sang them. 

For older people, I think it takes them back to their younger days. Younger people love these guys as well, though. I can play this at a library to a crowd of senior citizens and then go play to a bunch of young people at a bar or honky tonk and the response is remarkably similar.  

You also recently released a new original album, “Gently Used.” Will you be out on the road performing those songs anytime soon? 

[The Songs & Stories format has] worked well because there just aren’t that many venues left to perform at doing original music. So I’m still doing a handful of gigs each month pushing the new album. I’m bringing The Highwaymen to Nashville and NYC in the months ahead and my hope is that I can try and hit the road and do a blend of both Highwaymen gigs and ones doing my own stuff. 

I’ve always thought of myself as a songwriter first and foremost, but honestly I have as much fun doing The Highwaymen songs because there’s so many great songs to choose from. I love learning them and trying to make them my own.

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