[6] While her brother played Southern rock and her sister Britney Spears songs, she discovered the country genre for herself and counts the Chicks and SHeDAISY as her early inspirations.
[7] She received a full music scholarship to Belmont University in Nashville at age 18, but declined because her boyfriend persuaded her to stay in Ellaville with him.
After she broke up with her boyfriend and was noticed by Luke Bryan,[8] she moved to Nashville at the end of 2013 with about $1,000 of savings, a high school diploma, and her clothes in trash bags.
With a fake ID, she entered the music venues and bars and, after asking a bass player at the Honky Tonk Central on Broadway, she started to sing cover versions there weekly.
[10] After about two years of playing and writing songs, she was introduced to Universal Music Publishing Group by Robert Filhart, where she started as a staff writer.
[14][15][16] Hammack wrote "Small Town Hypocrite" while still being a staff writer, together with Jared Scott, about the breakup with her boyfriend who cheated on her, which eventually brought her to Nashville.
[28] In February 2023 Caylee announced a second album when releasing the first single "All or Nothing" which she wrote together with Tofer Brown and Thomas Finchum and produced with Dann Huff.