She is known for her camp and drag queen -influenced aesthetic. After being dropped from the label, she released a series of independent singles including " Pink Pony Club " which facilitated Roan's rise to prominence. Roan released her debut album The Rise and Fall of a Midwest Princess , as well as her second album "The Future" through Island Records which received critical acclaim. The album garnered a cult following and was a " sleeper hit " later being nominated for Album of the Year at the 67th Grammy Awards.
In , she released a follow-up single, " Good Luck, Babe! Several songs from her debut album subsequently entered various charts including " Hot to Go! Kayleigh Rose Amstutz was born in Willard, Missouri , on February 19, , [ 2 ] [ 3 ] [ 4 ] the oldest of four children. Roan began playing the piano when she was 10 or 11 years old [ 16 ] and began taking lessons at the age of Roan began uploading on her YouTube channel in , only posting covers and occasional original pieces.
Chappell, who died of brain cancer that same year. On August 3, , Roan released her first single, "Good Hurt". The song was reviewed favorably in Interview , which praised her "striking maturity and surprisingly deep vocals".
In , Roan moved to Los Angeles. Roan began working with songwriter and producer Dan Nigro in late Roan was unable to find a collaborator whom she liked as much. Roan moved back to Los Angeles in October to continue working on her music independently while working a series of odd jobs, including as a production assistant and in a donut shop.
She then earned a publishing deal with Sony , and by February , was able to work with Nigro again to create and release "Naked in Manhattan". It was described by NPR as a "queer girl bop" with lyrics that are "tender, nostalgic" and "flirty yet uncertain".
