“In My Dreams” by Sterling Drake

Born in Big Cypress, Florida in 1995, Sterling Drake moved west after high school to pursue ranching and eventually settled in Philipsburg, Montana. He developed his musical voice through years of work on ranches while simultaneously building a career as a touring musician and songwriter. Drake draws from deep wells of American roots music—country, folk, bluegrass, and Western swing—creating songs that explore themes of redemption, the cowboy lifestyle, and rural community. He received the Male Honky Tonk Artist of the Year award at the 2024 Ameripolitan Awards in Austin. His debut album The Shape I'm In was released in May 2025, featuring collaborations with acclaimed musicians and showcasing his growth from honky-tonk performer to seasoned artist.