Conversation #2: Josh Crutchmer
Striking the writing/editing balance between Red Dirt scene and the New York Times

Josh Crutchmer vividly recalls his “Waylon Jennings moment.”
It was January 27, 2001, a week shy of the 42nd anniversary of Jennings giving up a seat on the airplane that crashed in an Iowa cornfield, killing Buddy Holly, Ritchie Valens, and J.P. “The Big Bopper” Richardson.
Crutchmer, then the sports editor for Oklahoma State University’s student newspaper, had tried to arrange transportation with the men’s basketball team so he could cover a game in Colorado that night. But the flight was never confirmed, and Crutchmer opted to go to Cross Canadian Ragweed’s record release party at Stillwater’s Wormy Dog Saloon instead.
The plane crashed 25 miles east of Denver, killing all 10 people on board in one of the most devastating events in the university’s history. Word made it to the Wormy Dog, where Ragweed performed from midnight to 2 a.m. “because they didn’t know what else to do,” Crutchmer says.
“I always felt a little bit of guilt about it, because I was blowing off my job to see a bar band,” says Crutchmer, who “numbly” covered the aftermath for the newspaper while going to funerals for those who had been killed.
In the middle of his guilt and grief, Ragweed’s lead singer, Cody Canada, offered to take Crutchmer to the band’s show in Dallas. The trip cemented his friendship with Canada; the tragedy cemented his relationship with the Red Dirt music scene that he has since covered in several books and for Rolling Stone.
“In a strange way, it was what made me decide that I was as much a part of Red Dirt as the artists who were making it,” Crutchmer says of the near miss. “I wouldn’t advise any journalist to do something like that, but looking back on a personal level, it gave me some direction. The motivation to give back to this scene, this region, and this state was rooted in that experience all those years ago.”
Planning Ahead
Earlier this month, Crutchmer stood on a stage in front of more than 45,000 Ragweed fans for four consecutive nights and told the story as an introduction to the band’s “On a Cloud.” Days afterward, during a Zoom interview, he said that doing so was a full-circle moment during one of the most memorable weekends of his life.
In yesterday’s “Conversations” piece, we talked about the Cross Canadian Ragweed reunion and the Boys From Oklahoma shows. But I also was intrigued by the unique career path that Crutchmer has charted since graduating from OSU. It’s one that sees him toggling between his home state and Manhattan, working for the New York Times and Rolling Stone, and self-publishing books about the music he loves.
“Most of my journalism career has been spent on the design and editing side,” says Crutchmer, who was the managing editor for visuals at the Cleveland Plain Dealer when the Cavaliers won the NBA championship in 2016. “I got to direct pretty much how everything looks and how all of our coverage fit in the print edition because the online version was so templated.”
The Plain-Dealer received industry praise for the coverage, leading to Crutchmer’s being hired by the Times in 2017. Two years later, he was promoted to the planning editor role and now is in charge of a four-person team that selects the stories that appear daily in the print edition.
“We’re writing a thousand stories a day with ease, and that counts everything from major enterprise pieces to two paragraph briefs and audio clips and and video and podcasts. My team looks at our content as a whole and then tries to figure out which 50 or 60 pieces from that will make up a newspaper that day,” he says.
Crutchmer says the Times’ digital news reporting “drives everything about us as an operation,” but the print product remains “very important to our company.”
“If I just tell somebody I work for the print New York Times, that can sound a bit like you're describing yourself as a dinosaur,” he says. “But actually my team has to be some of the most knowledgeable in the entire company because we are tasked with scouring our global report every day and turning it into a newspaper.”
Juggling Multiple Roles
Given that type of role, how does Crutchmer find the time to write as much as he does? And does that conflict with his job at the Times?
Since 2020, Crutchmer has written a series of books focused on Red Dirt music, including the new Never Say Never, which is a real-time, on-the-scene report of the Boys From Oklahoma shows. The books are produced by Back Lounge Publishing, a company Crutchmer started. He also works contributes to Rolling Stone, focusing mostly on the Americana/alt-country/Red Dirt genres.
“A trade off with having to be plugged into the Times all the time is that my job can be done from anywhere. It’s really easy for me to be involved with the front page while on the back of Cody Canada’s tour bus or in a green room somewhere,” he says. “That’s allowed me to get out and travel and reconnect with my musical roots.”
Crutchmer says his supervisors know about and have signed off on his music-related work. “That’s just not something the Times covers topically more than once or twice a year, so as long as I promise them I will take them the big important stories, they’ve given me the blessing to put most of my writing in Rolling Stone or in similar places,” he says. “It’s just been wonderful.”
The juggling act, he says, is worth it because he’s getting to do what he loves — maintain ties to Oklahoma and its music while working at the highest level of his chosen profession at the Times.
As our Zoom call came to a close, I asked Crutchmer whether working as an editor and content curator has helped his writing or made it more difficult. Having done both myself, albeit on a much smaller scale, I find my writer and editor sides clash often, but the conflict often leads to better work.
“Being an editor at the Times and seeing how my colleagues craft their stories and question content has rubbed off so much in my writing. It’s helped me so much,” he says. “I question leads and headlines in a way that I may not have.
“It’s fun to sit here and feel like I’ve still got it as a writer, and to recognize that the career I’ve had has made my writing so much better than it would have ever been if I hadn’t had these opportunities,” Crutchmer says. “I’m truly grateful.”
The Boys From Oklahoma
The Boys From Oklahoma, a stadium-sized celebration of Red Dirt music that spanned four nights and saw a reunited Cross Canadian Ragweed return to the stage for the first time in more than a decade, brought fans from all 50 states and several countries outside the U.S.
I’m sheepishly admitting that the term “red dirt” as a genre is fairly new to me. I had the privilege of seeing Jimmy LaFave perform multiple times in Austin, where he lived for decades before his death in 2017. “You don’t know what you’ve got til it’s gone” applies here. We referred to him as a folk artist, but Outlaw Country was often used. Maybe it’s because we lived in the Heart of Texas where Oklahoma is a dirty word, but “red dirt” wasn’t a genre term I heard thrown around. Seems to me from reading red dirt history, that Outlaw Country and Red Dirt genres are almost one and the same with the exception of the artist hailing from a town built on red soil. Though red dirt also seems to encompass bluegrass as well. Thanks for the informative read that broadened my musical knowledge and got me digging deeper.
This is the first time I've heard the phrase "Red Dirt" music scene." Would that include Zach Bryan? Also, years ago a Cross Canadian Ragweed album came into my possession. I liked it a lot.