Andrews began songwriting at the age of 15 and released her first album Urban Myths in 2008 onRiver Jones Music when she was 18. She attended Barry Goldwater High School for two years and transferred to the Arizona Conservatory for Arts and Academics, graduating in 2009.

She has been a top 10 seller in Phoenix since 2008, and has performed alongside bands from Sub Pop, Barsuk, and Saddle Creek. Andrews has also performed at annual festivals in Phoenix. In 2008 she participated the First Annual Winter Folk Festival at Modified Arts. She participated in the 2009 Summer Folk Festival, the 2010 Final Folk Festival, and the 2011 RJM & Friends Fest.

In September 2009, Jim Adkins of the band Jimmy Eat World asked Courtney to do a duet of a Wilcosong featuring Feist with him live on stage. In 2010, Andrews recorded backup vocals for Jimmy Eat World on 5 songs for their album Invented. She subsequently joined them on stage to perform during the album's release and full 2010/2011 tours.