Upchurch began uploading videos to
YouTube and
Vine. In 2014, he and his friend Shade Glover created the humorous alter ego "Upchurch the Redneck" for their own entertainment. The character spoofed stereotypes of young men in the
Deep South, and the videos quickly went viral, gaining over half a million fans in just four months. While his early content was primarily comedic, he began incorporating rap-influenced "
hick-hop" videos into his content. He released his first extended play,
Cheatham County, in 2015, followed by a full-length album,
Heart of America, in 2016.
Heart of America sold 1,300 copies in its first week of release. A then-rising
Luke Combs appeared in the music video for Upchurch’s song "Outlaw". The video prominently featured
Confederate flag imagery, including a
decal on the acoustic guitar Combs was playing. During a Country Radio Seminar in February 2021, Combs publicly apologized for his past use of the imagery. He stated there was "no excuse" for the images and that he had since learned how painful that symbol can be to others. Upchurch immediately fired back on social media, calling Combs and other country stars "sissies" for "bowing down" to public pressure. He argued that the imagery represented Southern heritage rather than hate and felt Combs was being a "mainstream sellout" by distancing himself from his roots to appease record labels. The second full-length album,
Chicken Willie, was released in August 2016. It reached No. 22 on Billboard's Top Country Albums and No. 11 on the Rap Albums charts, selling 2,800 copies in the first week. In 2017, Upchurch released another EP titled
Summer Love, which is completely
country-oriented, with no elements of
rap music; and another studio album titled
Son of the South.
Summer Love, debuted at No. 33 in the Top Country Albums chart with 3,700 copies sold, while
Son of the South debuted at No. 29 with 48,100 copies sold. Upchurch's fifth studio album,
King of Dixie, was released on November 10, 2017, and features 19 tracks. Upchurch's first rock album,
Creeker, was released on April 20 which was focused on rock with few rap elements. His August 2018 release,
Supernatural, a rap-focused album with some country elements, peaked at No. 6 on Billboard's Top Country Albums. His December 2018 album,
River Rat, peaked at No. 22. The artist canceled a sold-out show at Alrosa Villa following neighborhood protests and flyers accusing him of promoting
white supremacy and offensive rhetoric. Upchurch released his next album,
Creeker II in April 2019. Later that year, he released
Parachute on September 24, followed by a collaboration album with
Adam Calhoun entitled
Hooligan on November 25. On April 20, 2020, Upchurch released his eleventh album
Everlasting Country containing a more traditional country sound. It peaked at No. 61 on the
Billboard 200 and No. 6 on the Country Albums chart. Country singer
Kane Brown briefly went missing in August 2020 after getting lost in the woods on his property, and Upchurch claimed he helped find him instead of the local police. In 2021, Upchurch founded his own record label Holler Boy Records with country singer-songwriter
Chase Matthew being the first signee, partnering with ONErpm. The two released a popular remix of Lil Durk's country-rap song "
Broadway Girls." The label became inactive in late 2022 when Matthew signed a major-label deal with
Warner Records Nashville. == Personal life ==