Haley has been making music since high school, when her first of many records was self-released before graduation. Her first punk band was called Frankie Horsesh*t, and a decade later she founded the punk/new wave band Gramma's Boyfriend, which she is the front woman and main songwriter for. Haley has published short stories and poetry, produced all of her 9 full length LPs, and self-recorded, produced, and released 5 EPs.

Until 2017, she released under the name Haley Bonar before choosing her maternal surname 'McCallum', shifting her stage name to just 'Haley'. Many of her songs can be heard in tv shows such as Orange is the New Black, Transparent, Arrow, United States of Tara, as well as commercials and film trailers. In 2013, Haley was awarded the prestigious McKnight Fellowship for performing songwriters. She has toured across the United States, Canada, Europe, and the UK.

In 2018, Haley composed her first full length instrumental album, Pleasureland, and created 6 of the album's 12 accompanying videos. Although she has been creating work for 18 years, the fact that it feels like Haley is just beginning is possibly the most remarkable thing about her artistry. Moving with confidence and vulnerability through genre and category, Haley's music engages the audience regardless of the direction it is coming from.