Jessie Jo Dillon: 5 Songs That Shaped the Songwriter

by Jim Casey

When your last name is Dillon, country artists expect songwriting superiority. Fortunately, Jessie Jo Dillon is living up to expectations. Jessie Jo, the daughter of Country Music Hall of Fame songwriter Dean Dillon, has forged her own path as one of Nashville’s top songwriters.

The two-time Grammy-nominated tunesmith has penned more than 900 songs over the last decade or so. Jessie Jo’s songwriting cuts include George Strait’s “The Breath You Take,” Cole Swindell’s “Break Up in the End,” Maren Morris’ “Rich,” Dan + Shay’s “10,000 Hours,” Brandy Clark’s “Girl Next Door,” and Tim McGraw’s “Here On Earth,” among others.

Jessie Jo sat down with Outsider to talk about the 5 Songs That Shaped the Songwriter.

1. ‘Boys of Summer’ – Don Henley

Jessie Jo Dillon: I have tried to rewrite this song 1,000 times. I love the aching and longing this song fills me with. The lyrics, emotion, and chorus melody are just inimitable. I adore this song, which was written by Don Henley and Mike Campbell. Always have and always will. I don’t know why, but it reminds me of my favorite book, The Great Gatsby.

2. ‘You Don’t Know Me’ – Ray Charles

Jessie Jo Dillon: Easily one of my favorite country songs of all time. I think almost every person on earth can relate to this song at some point or another. It is the quintessential unrequited, falling-in-love-with-a-friend song. Although I love many versions, Ray’s is my favorite. His voice is the one for me. Of course, the song was written by a woman, Cindy Walker, and Eddy Arnold. 

3. ‘Bowl of Oranges’ – Bright Eyes

Jessie Jo Dillon: Conor Oberst is a huge reason why I am writing songs today. I first heard his band, Bright Eyes, in my teens. And the rest is history. Lyrically, I draw huge inspiration from his honesty and interesting point of view. He has some lines that will always just blow me away. I remember my dad hearing this song and asking me who wrote it, because of some of Conor’s outstanding lyrics. “Bowl of Oranges” has such a cool perspective and tells a story I feel we can all relate to in our own ways.

4. ‘Oh, What a World’ – Kacey Musgraves

Jessie Jo Dillon: I dig everything about this song that was penned by Kacey Musgraves, Daniel Tashian, and Ian Fitchuk. I find it super inspiring all the way around. Really love the production, vocals, and the way they chose to say “I love you” in a new way.

5. ‘I’m On Fire’ – Bruce Springsteen

Jessie Jo Dillon: Written by Bruce, “I’m On Fire” is one of the sexiest songs ever! The Boss is the king. I love how simple this song is. But it is so emotional and cuts right through. I love how it feels and the guitar. I reference this song often because of how tasteful they made it. It is not overdone, it is perfect.