Maddie Wilson

Maddie Wilson

Jam Chats • Season 2, Episode 3
Oct 16, 2026 • 1h 6m

Hosts CJ and Reimy interview singer-songwriter Maddie Wilson, who shares how her non-musical parents supported her through lessons and performances, her small-town Utah upbringing surrounded by country music, and her path to Nashville for songwriting, recording, and writer’s rounds like the Bluebird Cafe. Maddie performs and discusses several songs: “Richest Man,” inspired by her late grandpa’s saying about being rich in family; “RIP,” a fun breakup song written in Nashville; and deeply personal songs “Your Room” and “Wounded,” reflecting infertility, IVF, miscarriages, and vulnerability through music. She also shares “Baby Blue,” about motherhood bringing light, and “Black Sheep,” about embracing being different. 00:00 Meet Maddie Wilson 00:37 Early Songwriting Roots 02:11 Choosing Music Over Sports 04:03 Country Upbringing 05:51 Richest Man Story 10:52 Recording Nashville Connections 11:57 Writers Rounds Bluebird 14:48 Live Song RIP 19:22 Infertility Miscarriage Journey 21:09 Song Your Room 29:11 Vulnerability Through Music 32:43 What Not To Say To Someone Battling Infertility 33:12 Fixing Versus Listening 35:02 Live Song Wounded 39:13 Why Sad Songs Heal 39:57 IVF And Newborn Life 42:39 Live Song Baby Blue 49:28 Faith Through Infertility 51:37 Motherhood And Music 54:43 Black Sheep Origins 59:09 Live Song Black Sheep 01:03:48 Success And Farewell