Greylan James Talks Writing with Kenny Chesney, Touring with Old Dominion & More

James chatted about what happened the first time he wrote with Kenny Chesney in person, and the “pinch me” moment that happened on tour with Old Dominion.


Nicole Palsa


Posted on March 6, 2023

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Greylan James; Photo Courtesy of Trea Allen

Knoxville, Tenn. native Greylan James received a call from superstar Kenny Chesney in 2020 that he would be recording a song that James penned, called “Happy Does.” That song skyrocketed to No. 2 on the Billboard Country Airplay chart and was the start of James’ professional relationship with Chesney. Since signing a publishing deal with Universal Music Publishing Group in 2018, James has had his songs recorded by Chesney, Cole Swindell, Jordan Davis, Chris Young, Blake Shelton, and more.

With motivation from artists like Cole Swindell, James made the leap from songwriter to artist, releasing his debut single “Anything Cold” in February 2022. Since then, he’s released a handful of singles and has kicked off 2023 with a pair of songs that were inspired by the impacts of a breakup he experienced.

Greylan James; Photo Courtesy of Trea Allen
Greylan James; Photo Courtesy of Trea Allen

James caught up with Music Mayhem to chat about his new single “Two Years Back,” what happened the first time he wrote with Kenny Chesney in person, and the “pinch me” moment that happened on tour with Old Dominion.

In January, James released the track “My Future,” which was the result of writing “half songs” to get out of a rut. He and his co-writer Matt Roy had had a rough couple of weeks writing with strangers and feeling a bit defeated about their songwriting, so they decided to meet up and start writing through titles, “to remind ourselves that we can actually write a song.”

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James was going through a breakup around the same time, after two and a half years of dating that person. “That title [My Future] got thrown out there and we started kind of writing it and we’re like, okay, this is not something we’re just going to start. We need to finish this,” recalls James.

For the first time, he witnessed a reaction to a song before it was fully released. “People were really relating to the song,” he says. “To see people commenting that they want to send this to their ex or to somebody that they want to rekindle with is a special thing that I’ve not experienced until this song.”

James penned his new single “Two Years Back” with Roy and Brock Berryhill about the same relationship that birthed “My Future.” In the song, James describes how he wouldn’t change anything about the two years he spent with his ex, despite how it ended. Shooting the music video for the deeply personal track was special for James. “I just love watching songs come to life. So much of what we do as songwriters and artists is kind of a manifestation in your head and you kind of imagining what the story is and you see the characters in your head. To see that come to life with actors and cameras around and see it through a screen in the back is just a special experience.”

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Although James has written with Kenny Chesney before, he recently experienced it in person for the first time. “I’ve written some songs kind of over the phone, texting, calling back and forth cause he was on a stadium tour casually all last year.”

On the first NFL playoff Sunday of 2023, James met up with Chesney, who had a small window of time to make it happen. “It was just wild showing up to write with Kenny Cheney. He has become a friend and a good mentor over the past couple years to me. But it’s still those little moments that I’m showing up and pulling in the driveway, I’m like, this is weird. I can’t believe it.”

Part of that unusual experience was giving and receiving constructive criticism about lines in a song. “It’s funny cause that’s how writes work, but to do it with somebody that you grew up kind of worshiping and idolizing is kind of an out-of-body experience. But it was fun. We got a good song that day and we’re doing it again and hopefully we’ll be doing a lot more times.”

The first piece of advice that Chesney ever gave James was to “stay in school and learn how to write songs.” James was only 11 years old at the time, who had a split-second encounter with Chesney at a private show in Knoxville. “He was the guy that was on the posters on my wall,” he reminisced. “I’d got a C on my science test that day and my parents were mad at me and I told them, I’m like, mom, dad it’s chill. I want to be a country music star. Don’t worry about it. I don’t need science.” James’ dad asked Chesney what his advice would be for the aspiring singer. “Stay in school and learn how to write songs. And it’s always been something that stuck with me and it got me through middle school and high school and when I moved here I always kind of remembered the writing songs part so I’d go to that.”

These days, Chesney mentors James about live performances. “Getting to talk to Kenny before I was going out on tour with OD [Old Dominion], that was when we were writing, and Kenny was giving me little pointers here and there on how to work a catwalk and make sure to have condition and how to interact with fans, pay attention to people in the rafters, and just really small, detailed things that I can’t believe I get to learn from the best.”

Old Dominion also credits Chesney for the quality of their production. “They give a lot of credit to Kenny for how good their live show is and they’ve learned both on stage and behind the curtain on how to conduct their business,” says James.

Even though he’d received advice from Chesney about working a catwalk, the actual experience was still surreal for James.

“The most pinch-myself moment was definitely the catwalk. I’ve never had a catwalk in my entire life and I don’t really work out and I don’t really condition. I definitely don’t have that Kenny Chesney or Tim McGraw body by any means,” he laughs. “I got out there and it was a lot bigger than I guess I expected it to be. And I have a wireless pack and a wireless microphone and they encourage you to use the catwalk. So I’m like, all right. And I get out there for rehearsals the first day to run a show and I’m trying to run up and down that catwalk, like a Mick Jagger, and I’m like, I’m out of breath. Bad. Like this thing is massive and I just, I’ve never taken it into consideration.”

Now, James is working on his fitness to tackle the large stage. 

“Last year I was playing small clubs and small theaters and with great crowds, but just doing this is, it’s what you dream of. And getting to go out there and see that many people that in tune to country music is, it’s a special experience and I can’t be more thankful to the people that are coming to the shows for just letting me have my 20 minutes at the start.”

James is currently on the road with Old Dominion on the No Bad Vibes Tour, which runs through July 1. For a full list of dates and ticket details, visit

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