The Writers Round with Jessie Jo Dillon

This month, Jessie Jo Dillon sheds some light into her life as a songwriter as well as shares the stories behind some of her many hits.

Written by Annie Reuter
The Writers Round with Jessie Jo Dillon
Jessie Jo Dillon; Photo Credit: Kate York

Welcome to the Writers Round, a monthly column where Sounds Like Nashville sits down with Nashville-based songwriters and learns about each writer’s journey to Music City. This month, Jessie Jo Dillon sheds some light into her life as a songwriter as well as shares the stories behind some of her many hits including George Strait’s “The Breath You Take” and Brandy Clark’s “Daughter.”

Songwriting runs in the family for Jessie Jo Dillon. The daughter of Nashville Songwriters Hall of Fame inductee, Dean Dillon, she admits that her father was often a huge shadow to be in. As a result, Jessie Jo frequently discouraged herself from becoming a songwriter. It was only a matter of time, though, that she realized music was her true calling.

Dillon grew up in a musical family with her songwriter father and two musically inclined brothers. She remembers being surrounded by music with everything from country to rock ‘n’ roll from the ’60s and ’70s being played in her home. The Eagles, the Rolling Stones, Led Zeppelin and Bob Dylan were frequently on the speakers and she recalls constantly writing as a child.

“I was always fascinated with words and the way they made people feel,” she tells Sounds Like Nashville over the phone during a break from a writing session. “I had an English teacher that encouraged me all the way through, ‘You’re a writer, you’re a writer,’ [she said] even when I was trying to discourage myself from doing it.”

Adamant about not following in her father’s footsteps, Dillon moved to Los Angeles for a year where she soon found her songs being critiqued by a woman in publishing who urged her to go home. Taken aback at first, she thought the review was harsh but that wasn’t what the woman meant.

“No. You really can do this but you’re a country songwriter,'” she recalls her saying. “You need to go home because you really can do this.”

That was the push Dillon needed and she moved home around 2008 where she hit the ground running, but again was determined to do things her way. She didn’t want anyone to think she was joining the trade because of her father so she put more pressure on herself to strike out on her own and her hard work eventually paid off when she acquired a publishing deal a year later at the age of 21.

In 2010, she’d receive her first Grammy nomination for her very first cut, a song she wrote with her father and Casey Beathard called “The Breath You Take” that George Strait recorded. The song was nominated as Best Country Song at the 2011 awards ceremony. Dillon had the idea for “The Breath You Take” and called her dad and told him about it. That day he was writing with Beathard and invited his daughter to join them.

“We wrote it super quickly and I think it meant the same thing to all three of us, even at different stages in our lives: slow down and take it all in,” she explains. “We get so caught up in trivial things that don’t really matter in the grand scheme and it is just a moment of, ‘You’re going to miss the point of all of it if you don’t take it all in.’ That was a really special song for all three of us.”

Dillon is still in awe that King George recorded her song and the fact that it was recognized by the Recording Academy, admitting that a Grammy nomination is something she has dreamed about since she was a little girl.

“I even still feel a little speechless. The fact that your song would’ve mattered to your peers and others, that touches my heart so deeply to think I could ever have been a part of something that spoke to someone else,” she says. “I grew up loving Don Henley, Bobby Braddock [and] Hank Cochran [and] I would sit there and I think, ‘Man, I feel like this person knows me. This song speaks to me so much.’ It gave me that feeling of, ‘Gosh, well maybe I’ve made somebody else feel that way, too,’ and it was just the utmost honor.”

Dillon recently signed as a songwriter with Big Machine Music and finds herself frequently writing with friends and fellow Grammy-nominated songwriters Maren Morris and Brandy Clark. She shares a kinship with Clark, having written several songs featured on the singer’s last two albums and says she feels like they were “both born a little broken-hearted and we speak the same language in that way.”

“She’s like a sister to me. We are drawn to the same characters and instances in life and in song. It’s kind of the life of the black comedy look at things,” she admits.

Dillon had a hand in penning three tracks on Clark’s Grammy-nominated country album Big Day In a Small Town including previous single “Girl Next Door,” “You Can Come Over” and the striking “Daughter,” a song she says was inspired by a man she and her co-writers know.

“Me and her and Jeremy [Spillman] were talking about a guy that we all knew and I had been telling a story about how I’d seen him being a jerk to a certain girl and Brandy was like, ‘I hope he has a daughter,’ and we were all like, ‘That’s amazing! Let’s write that song,'” she recalls. “It’s the ultimate, ‘you better think twice,’ for a man because it’s all fun and games until she is your daughter. So many guys, whether it’s co-writers or guys I know, have said, ‘I love that song but damn. It really made me think.’ It’s funny to hear the guys are into that song at all because it is so striking.”

Being the daughter of a respected Nashville songwriter, Dillon herself has learned many lessons firsthand from her father. While songwriting is her ultimate passion, it is also a job now as she continues to write professionally for a living. She admits that some days are more difficult than others and oftentimes she has trouble figuring out what to say as well as finding new melodies.

“He was always telling me, ‘Go fishing. Go out of town on a writing trip,'” she says of moments where she has writer’s block. “Go chase ideas somewhere because you’re going to find them and sometimes you have to fill the well back up. Keep your ears open at all times because that’s where so many great ideas come from. It’s just listening to other people and taking yourself out of your normal environment and going and doing something else. I definitely believe that to be true, especially filling the well back up so you can draw from it again.”

Now signed to Big Machine Music, Dillon can’t remember a day where she wasn’t writing and she plans on keeping it that way.

“Gosh, I just love it. I just love songs. I love music. I love the way they make me feel. There’s nothing in my life that’s quite like it that I’ve experienced thus far. It’s magical to me and I don’t know if I could do anything else,” she concedes. “It has always spoken to my heart and I don’t know what I would do without it or without getting to be a part of it.”