The band released their debut album, Skeleton Crew, in May 2015 on Glassnote Records.

They also supported The Tallest Man on Earth, Sufjan Stevens, Pixies, Rodrigo y Gabriela, and Old Crow Medicine Show.

That same year, Madisen Ward and the Mama Bear appeared on NPR Music's Tiny Desk Concert.

[3] The band's second full-length, Started with a Family, was released in September 2019, produced by Nathan Chapman, engineered by Jeff Balding and Lowell Reynolds, mixed by Nathan Chapman, and mastered by Ted Jensen at Sterling Sound.

It was recorded at Blackbird Studio, Nashville, in Studio C. On tour, their backing band consists of Brent Kastler (bass), Tom Hudson (drums), and Larissa Maestro (cello).