Jessie Jo Dillon

by Amanda Flinner

The Nashville hitmaker shares the stories behind her biggest co-writes, including the crossover hit "10,000 Hours."

Jessie Jo Dillon has songwriting in her blood. As the daughter of veteran Nashville scribe Dean Dillon - who penned an array of hits for George Strait, Kenny Chesney, and Toby Keith - Jessie Jo knew she had some pretty big cowboy boots to fill when she joined the family business. As it turns out, they were a perfect fit.

Jessie Jo's first song was also her first hit: She co-wrote George Strait's "The Breath You Take" with her dad, and it landed in the Country Top 10 and was nominated for a Grammy Award for Best Country Song. Since then, she's brought a blend of heart, humor and grit to hundreds of songs, including Cole Swindell's "Break Up In The End," Maren Morris' protest anthem "Better Than We Found It," and Dan + Shay's crossover smash "10,000 Hours," featuring Justin Bieber. The latter tune also won the Grammy Award for Best Country Duo/Group Performance in 2021.

In this Songfacts interview, Jessie Jo takes us behind the scenes of some of her biggest hits and shares some words of wisdom from her dad.
Amanda Flinner (Songfacts): You found success right out of the gate with George Strait's "The Breath You Take." When I spoke with your dad back in 2016, he recalled warning you, "Don't get too spoiled, it's not this easy." Do you think having that immediate success helped you or hindered you?

Jessie Jo Dillon: My dad was right! I think it did both, helped and hindered. Helped in the sense that I was able to get co-publishing straight out of the gate in my first publishing deal because I already was going to have a single coming out. It allowed me to get in writing rooms I'm sure I had no business being in at the time. It hindered in that... I would be lying if I said I didn't have many frustrating years following that song.

There were a lot of singles that died, a lot of cuts that were never singles, and sometimes no cuts at all. I think that is part of this town though, so I guess it's not really a "hinder" specific to me because everyone that comes through Nashville deals with it. Music Row makes you pay [laughs]. Either in the beginning, middle, or end. If you haven't cut your teeth and paid your dues, it will make you. Your number is gonna come up sometime. I just had to keep pushing myself to keep going when I wanted to quit.

Songfacts: What first sparked the idea for "Better Than We Found It," and why did you think it was a good fit for Maren Morris?

Dillon: Last August, I wrote the sentence down in my phone, "I wanna leave this world better than I found it." I was so saddened and paralyzed by the state of our country and world at the time. All of this violence, hatred, brutality, and anger seemed to be everywhere I looked. Jimmy Robbins, Laura Veltz, Maren and I are all similar souls and I knew they were feeling it too, so I brought the idea in to them the next day.

Maren is an incredible woman and artist in so many ways, but one of the biggest jewels in her crown is her willingness to use her platform to help people, shed light on hard topics others shy away from, and spread love and equality. We had been talking about old '60s/'70s songs we dug that pointed right at what was going on at that time, and we wanted to do the same about what was going on in our time. It starts with us in our own communities and the small and big things we can do every day to help and speak out for others and ourselves. To quote Dave Chappelle, "Maybe you can't change the world, but you can make a little corner of it pretty nice."

Songfacts: With so many successful co-writes to your credit, you're obviously a great team player. What do you think your greatest strength is as a songwriter?

Dillon: I just genuinely love collaboration and I have no ego in a writing room - I leave that to the guys to sort out [laughs].

When I'm writing what I think is a great song, I get really excited in the room and hope to bring out the best in everyone and let them know they're safe to say or play things they might think are stupid, because nothing is stupid in a writing room... it could lead to something brilliant.

I say silly things all the time, but there is a thin line between silly and genius. Now, I can lay the hammer down if I think we are getting off course, but my co-writers do that for me, too. I also have a pretty high bar for songs. I am heavily influenced by all the juggernaut craftsmen and women that came before me in this Music Row town. A song shouldn't be "good," it should be "great." I'm blessed to get to work with some of the most talented songwriters and artists in the world. They make my job easy.

Songfacts: If you had known that Justin Bieber was going to feature on "10,000 Hours," would that have affected how you wrote the song?

Dillon: Hell yes I would have written it differently! I would have overthought the song and probably screwed it up because Justin is in a league of his own, his star shines so brightly. I would have been intimidated by his body of work. Dan Smyers walked in with the idea for "10,000 Hours" and I remember saying, "Okay guys, the worst thing we could do today is over-complicate this song. It needs to be simple like good love can be." So we did just that, and wrote what I think is a simple and classic love song.

Songfacts: It's so interesting how a book title like John Dies At The End led you to write "Break Up In The End." What's an example of another song that came from a similar circumstance?

Dillon: "I'll Be The Sad Song" by Brandy Clark was inspired by a Zelda Fitzgerald quote. She had written a letter to F. Scott when their marriage was falling apart and said, "Save me the waltz." That struck me so much and broke my heart in the best way. I was in a similar spot to Zelda at that time and I wanted to write a song about it.

Chase McGill and Brandy were the best people to try and wrangle that idea with, and I think it turned out to be such a beautiful and haunting song. "I couldn't be your happy song, but at least we had a song, so I'll be the sad song you sing."

Songfacts: Sunny Sweeney recently appeared on the Songfacts Podcast and told us she almost thought "Bad Girl Phase" was written about her because she resonated with it so much. What do you recall about writing that song?

Dillon: Sunny and I are cut from the same cloth! I vaguely remember it being Shannon [Wright]'s idea.

I love that song so much and loved writing it. I've been called a lot of things in my life, but a "good girl" isn't one of them. My dad is basically an outlaw and always told me girls can be one, too. I smoke, I drink, I cuss, and live a colorful life. That isn't the usual archetype of a put-together Southern woman. Men are celebrated for that same behavior, so why can't women be?

I wanted to write something for all the bad girls out there, real and fictionalized. I've always looked up to the girls that have been unabashedly themselves and make few apologies about it... Stevie Nicks, Joan Harris from Mad Men, Debbie Harry, Gloria Steinem, Sheryl Crow, Samantha Jones from Sex And The City, Zelda Fitzgerald, Janis Joplin... I could go on and on. I love the line, "Good girls go to heaven, bad girls go everywhere." Kinda sums it up. God bless Jackie Kennedy for being able to smile through it all, but I've always been a bit more of a Marilyn.

Songfacts: You've said many of your most popular songs came together quite easily but on the flip side, what's an example of one that was a true labor of love?

Dillon: Gosh, so many. Some songs are that way, though. I think they want to be born when they want to be born. I was told a story one time about Harlan Howard being asked how he could write hit songs so fast. He said, "I've never written a song fast. Those ideas have been rolling around in my head for years." I've never heard it said better.

Songfacts: The BMI Repertoire credits you with well over 900 songs. What song in your catalog do you feel deserved more attention than it got?

Dillon: I have a song in my catalog called "Dreamers, Drinkers, And Broken Things." It was once recorded by Keith Urban, but never released. I wrote it with Jessi Alexander and JT Harding and it's one of my favorite songs I have ever written. I hope it sees the light of day sometime. It is kind of an anthem for all of us beautifully messed up humans out there.

Songfacts: Growing up in a musical household, you were certainly exposed to a lot of different music. What song by another writer had the most influence on you, and why?

Dillon: Rather than a song, it's actually an artist. When I was about 15 or 16 and first heard Conor Oberst of Bright Eyes, it changed my life. I was blown away by his lyrical ability and brutal honesty. The way he says things cuts me like a knife. I love every single one of his records and I dove in deep. I remember thinking, "Good Lord, I wanna write like this." In my dreams Conor has heard songs like "Break Up in the End" and has thought, Damn, that is great.

Songfacts: Finally, is there any song that we didn't cover that you'd like to talk about?

Dillon: I have two songs coming out in May I am stoked about. One, called "Grow Up," was recorded by Ian Flanigan feat. Blake Shelton (also was recorded by Kenny Chesney, but was never released), and the other was recorded by a new artist I'm so excited about, Conner Smith. Look out world :)

April 26, 2021

Follow Jessie Jo Dillon on Instagram

Here's our interview with Dean Dillon and our podcast episode with Sunny Sweeney

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