Chase began uploading unfinished music and covers in 2018. He released his first real debut song "Nashville Crazy" in April of 2019. After a few more releases, he caught the eye of country rapper Upchurch (musician), and in June of 2021 Ryan signed Matthew to his new independent record label Holler Boy Records. His debut song for the label "County Line" debuted and peaked at number 28 on the Billboard charts Hot Country Songs chart and peaked at number 12 on the Bubbling Under Hot 100 chart. A m...