Jackson Dean

With an easygoing manner paired to old-school grit, country singer-songwriter Jackson Dean first built a regional following before relocating to Nashville. There he signed with Big Machine and issued his self-titled EP in 2021. Breakout traction arrived with “Don’t Come Lookin’,” the track that anchored his first full-length release, Greenbroke, in 2022. A live set, Live at the Ryman, reached listeners in April of the next year, preceding the September 2024 arrival of his sophomore album, On the Back of My Dreams.

Raised in Odenton, Maryland, Dean left home at eighteen and sharpened his writing inside a solitary cinderblock shack that lacked heat or plumbing. Working alone and with co-writers Luke Dick and Casey Beathard, he tested material at local shows that eventually found him opening for Kane Brown, Jake Owen, and Brothers Osborne. Big Machine Records took notice in 2020 and added him to the roster. Early the following year the single “Wings” preceded the April release of the self-titled EP. Placed on Paramount’s Yellowstone, “Don’t Come Lookin’” reached number three on Billboard’s Country Airplay chart and crossed into the Hot 100, generating momentum for Greenbroke, which appeared in early 2022. The album’s second single, “Fearless (The Echo),” surfaced in several versions throughout the year; its live edition closed the eight-song concert recording Live at the Ryman in 2023. Dean previewed his next project with the measured single “Heavens to Betsy,” and On the Back of My Dreams arrived in September 2024. Once again produced by Luke Dick, the concept album traced a path from light into darkness. He supported the release by touring with Lainey Wilson.