Caylee started playing music at age 13 which helped her to feel different in her hometown where she never felt like she belonged anywhere. While not getting much of a music education or vocal lessons, she self-taught by listening and singing songs on the country radio. The first time she had to turn down potential scholarships was after a surgery to remove a tumor as a fiften-year-old. This was also the first time she wrote her own song called "Addictive" about the pain pills she had to take after the surgery. While her brother played Southern rock and her sister Britney Spears songs, she discovered the country genre for herself and counts Dixie Chicks and the SHeDAISY as her early inspiration. Her first ticket to Nashville was her full music scholarship to Belmont University at age 18 which she ended up declining because her boyfriend persuaded her to stay in Ellaville with him. After the two broke up, she started to follow her interest in music again and a call from Luke Bryan gave her the final motivation to move to Nashville. She moved at the end of 2013 with about 1000$ of savings, a high school diploma, her cloth in trash bags, and playing Kacey Musgraves debut album for the seven-hour drive. She soon found herself sleeping in her car after spending the money she came with. With the help of a fake ID she could enter the music venues and bars and after asking a bass player at the Honky Tonk Central on Broadway she started to sing there weekly, covering songs. Before her signing an official recording contract she performed several original songs including "Redhead".
Career
After about two years of playing and writing songs, she was introduced to Universal Music Publishing Group Nashville by Robert Filhart where she started as a staff writer. During a writers' retreat she found out that her house in Nashville burned down due to an electrical fire that destroyed about 70 percent of her belongings. Tenille Townes was at the retreat with her and helped her during this time which was the start of their friendship. She's signed to Red Light Management and is managed by Mary Hilliard Harrington. In 2018 she could sign a recording contract with Capitol Nashville. She was featured as an emerging country artist by Billboard and as a new country artist you need to know by Rolling Stone and calls Kacey Musgraves, David Bowie, Tom Waits her influences in her adult life. In 2019 she could open for Lanco, Dierks Bentley, Trisha Yearwood, and Miranda Lambert. Her debut song "Family Tree" was released on January 18, 2019 and was the most-added debut song by a female artist at country radio in the last three years. Later, on May 29 she could perform the song on the Today show in her national television debut. Her upcoming album will make her debut as a producer for which she got help from fellow producer Mikey Reeves. Caylee wrote "Small Town Hypocrite" while still being a staff writer together with Jared Scott about the breakup with her boyfriend that cheated on her and which eventually brought her to Nashville. Later she found out that he lived in a double-wide trailer, which made its way into the song’s final verse. The song was officially released on February 21, 2020. She was scheduled to open for Reba McEntire and Luke Bryan in 2020 but the COVID-19 pandamic cut her Europe tour short and the opening acts for Reba were postponed which left the musican and her band with no income. During this time they started to offer a landscaping service to make up for the lost income. Caylee learned about her first-ever ACM nomination for New Female Artist of the Year for the 2020 ACM Awards while waiting for her plane at the airport. She hosted a Facebook event together with Ashley McBryde called CMT Next Women of Country Goes Live on April 7, 2020 and appeared on Country Outdoors LIVE special from Outdoor Channel on May 8. She announced on June 24 that her debut album If It Wasn’t For You will be released later in August and will contain 13 songs. She co-wrote 12 of them and wrote on by herself. The album features duets with Reba McEntire, Ashley McBryde, and Tenille Townes.
