Off The Record - An American Songwriter Podcast

Jessie Jo Dillon: Dad Dean Dillon, ACM Award Three-Peat, and Writing “Am I Okay”

September 30, 2026·52 min
Episode Description from the Publisher

On this episode of Off the Record, host Lisa Konicki talks with hit songwriter Jessie Jo Dillon, the first songwriter ever to win ACM Songwriter of the Year three years in a row. The episode opens with a game that pits her own hits against each other and includes a video tribute from actor-singer-songwriter Luke Grimes praising her work on his album Red Bird.Dillon talks about growing up as the daughter of legendary songwriter Dean Dillon, why she avoided songwriting at first, and how she approaches her craft: lyrics first, one clear emotion, and a focus on what the artist wants to say. She also shares stories behind hits like "Am I Okay?" with Megan Moroney, "10,000 Hours" with Dan + Shay and Justin Bieber, and Jelly Roll's FIFA anthem "Lighter."The episode ends with her new imprint, Gatsby, which she named after her favorite novel, and its first artist, Carter Faith. She also leaves us with advice to aspiring writers: “write from the heart and outwork everyone.”Let’s go Off the Record with Jessie Jo Dillon. Learn more about your ad choices. Visit megaphone.fm/adchoices

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