Taylor Ray Holbrook was born and raised in Pennington Gap, Virginia. He worked as a lumberjack before gaining an interest in music. This included posting videos of his songs to social media such as Twitter and Facebook.[1] In 2015, his single "Steal My Kiss" appeared on the Billboard Hot Country Songs charts, which inspired Holbrook to move to Nashville, Tennessee. He continued to record throughout 2016 and 2017, including a collaboration with Upchurch titled "Southern Land".[2]
Both the Upchurch collaboration and a 2016 single titled "These Hands" also made the Billboard country charts.[3] Country rap artist Colt Ford also featured Holbrook on the track "Reload" from his 2017 album Love Hope Faith.[4]
Rachel Whitney, a representative of country music programming for Pandora, observed that the service added his music to their platform after noting a large number of searches for his name. She cited this as an example of the service's ability to draw awareness to independent artists.[5]