Calhoun started his music career performing with
country rap singer, Chris Hosier. They released a single "Salute the Brave" in 2017, which reached No. 46 on Hot Country Songs. and they also released an album
Made in America that year. He ended his collaboration with Hosier and started a solo career in 2018, and released
AmerAcal. Later in the year he released his second album
The Throne. A track in the album, "Racism", drew criticism for use of the
racial slur "
nigga" and stereotypes about white and black people. In a collaboration with fellow American country rapper/singer
Upchurch with the song "Back N Forth", Calhoun notably raps about men wearing women's dresses. He released an EP
Crazy White Boy with Demun Jones. During their "Crazy White Boy Tour", their shows in
Sacramento, California, were scheduled in the same weekend as the Sacramento Pride, which led to protests because of his social media posts on gay and trans people and song lyrics described as "racist". It resulted in those shows being cancelled. Other shows similarly faced protests and another show in
Oklahoma City was canceled. On July 18, 2019, Calhoun released his third solo album,
War. The album was the second best-selling country album and the third best-selling rap album of the week, with 3,200 copies sold. Calhoun has also collaborated with a number of other artists, including
Upchurch on
Hooligan released in 2019, and
Struggle Jennings on
Legend, released in 2020. In September 2023, Calhoun and MacDonald released the album,
The Brave II. ==Personal life==