Allen was born in Milton, Delaware, United States, but moved to Nashville, Tennessee, in 2007. During most of his first few years in Nashville, he experienced poverty and often lived out of his car. Allen auditioned for America’s Got Talent, but did not make it past the preliminary auditions. He also auditioned for the tenth season of American Idol, but was cut before the live voting rounds. While on American Idol, he performed with Colton Dixon during one of the group rounds and befriended Scotty McCreery, who eventually won the competition that year. Allen and McCreery later reconnected and toured together after the release of Allen’s debut album.
Allen signed a publishing deal with Wide Open Music, a songwriting imprint formed by singer-songwriter Ash Bowers, in 2016. After doing a talent showcase for representatives of Broken Bow Records in early 2017, he was signed to that label’s Stoney Creek imprint and released his self-titled debut EP, which Bowers produced. The label’s executive vice president said that the decision to sign Allen was “one of the fastest they ever made at the label.” Stephen Thomas Erlewine of AllMusic compared the EP’s sound to the “slick, assured style” of Thomas Rhett and Sam Hunt. Similarly, Rolling Stone Country writer Brittney McKenna compared Allen’s contemporary R&B influences to those artists and Maren Morris. A track from the EP, “Blue Jean Baby”, was added to Spotify’s “United States Viral 50 chart”.