Childers began performing in
Lexington, Kentucky, and
Huntington, West Virginia. In 2011, when he was 19, Childers released his first album,
Bottles and Bibles. He released two EPs recorded in 2013 at Red Barn Radio, a radio show from Lexington. The two EPs were later released as one recording called
Live on Red Barn Radio I & II after the success of his album
Purgatory; they reached No. 5 on
Heatseekers Albums. He performed with his band, The Food Stamps, backing him. He first had success with the 2017 album
Purgatory. It was produced by
Sturgill Simpson and
David Ferguson and recorded at The Butcher Shoppe in
Nashville. Simpson also played guitar and sang backing vocals on the album; Miles Miller is on drums, Stuart Duncan on fiddle and Russ Paul played other instruments. It debuted at No. 1 on
Billboards Heatseekers Albums chart, No. 17 on the Country albums chart and No. 4 on the Americana/Folk albums chart. The video of the lead single from the album
House Fire was released on May 16, 2019. "All Your'n", the second single from the album, was nominated for
Best Country Solo Performance at the
62nd Annual Grammy Awards. On September 18, 2020, Childers released
Long Violent History, an album consisting mainly of traditional fiddle tracks. The album closes with the title track, which discusses racism, civil unrest, and police brutality. He released a video message to accompany the song; in it he discussed his intention for the album in general and the title track in particular, calling for empathy above all else. He said the profits from the album would support underserved communities in the
Appalachian region, through Childers' Hickman Holler Appalachian Relief Fund. On September 30, 2022, Childers released a triple album
Can I Take My Hounds to Heaven?. The album is divided into three parts: Hallelujah, Jubilee, and Joyful Noise; eight songs are presented in three ways (Jubilee versions for example have additional instruments added to the Hallelujah version). The album charted at No. 8, which is Childers' first top 10 album on
Billboard 200, based on 27,000 units earned in the first week. In that same year, he gave his song "Jersey Giant" to
Elle King which she included in her album
Come Get Your Wife. ''Rustin' in the Rain'' was released on September 8, 2023. The album features a cover of
S.G. Goodman's song "Space and Time". Childers was announced as one of the headliners in the 2024 Bourbon & Beyond festival in his home state, taking place in Louisville in September. Childers contributed a previously unreleased live version of the song "Bus Route" from his Country Squire album to the "Cardinals At The Window" benefit album, which was released in 2024. All proceeds from "Cardinals At The Window" go directly to organizations assisting western North Carolina communities
impacted by Hurricane Helene. Childers released his seventh studio album,
Snipe Hunter, on July 25, 2025, where he blended
Appalachian music,
experimental rock,
psychedelia, and
gospel music. In the album, he explored themes such as death, faith, personal myth, and regional identity. ==Musical style==