Country music breakout Jackson Dean sat down for an incredibly candid, laugh-out-loud interview at the Boots & Barstools concert in Tulsa, and it’s an absolute must-watch for any music fan.

From his surreal experience hearing his tracks score Kevin Costner’s iconic scenes on Yellowstone, to his wild, pre-fame gig working as a literal pirate on the Chesapeake Bay, Dean proves his life story is just as gritty and fascinating as his songwriting. He pulls back the curtain on his live performances — revealing the unexpected, crowd-shocking instrument behind his favorite track “Train” — and dives deep into the ethereal, bone-chilling backstory of filming his hit “Heavens to Betsy” during a brutal Montana blizzard. Packed with effortless charisma, creative secrets, and a playful promise to give the host a tattoo next time he’s in town, this interview captures the raw, unfiltered charm of a true modern outlaw.