Leatherwood cited traditional country artists such as George Jones, Merle Haggard, and Conway Twitty as his inspirations when it came to deciding to learn the guitar and pursue music.
Three of the four coaches, John Legend, Gwen Stefani, and Shelton, turned their chairs for him, with Leatherwood choosing to become a member of Team Blake.
[8] Leatherwood advance to the finale, where he was named as the winner of the season on December 13, 2022, earning a $100,000 prize and a record deal with Universal Music Group.
[10][11] Since winning The Voice, Leatherwood has played at his coach Blake Shelton's bar chain, Ole Red, on multiple occasions.
On December 18, 2023, Leatherwood returned to The Voice during the season 24 finale episode to perform his first major label single, "The Finger".
[14][15] In a December 2023 interview, Leatherwood stated that he had written 78 songs in preparation for an upcoming debut studio album he planned to release in September 2024, in addition to going on tour with multiple country music artists, including Dwight Yoakam.
[15] In February 2024, Leatherwood released a second single, "Neon Does," which he co-wrote alongside songwriters Alex Maxwell and Matt McKinney.