Growing up in Charlottesville, Bollinger often sang with her music-therapist mother, and she looked on while her older brothers were busy with music projects in the basement of their home. She began sharing her own self-recorded songs online in 2013, and before long, the singer/guitarist began playing shows locally. After a few years of issuing hand-distributed CD-Rs, she released her first official EP, Key West, in October 2017. Produced by Jay Purdy and Todd Erk, it featured members of Philadelphia indie rockers the Extraordinaires as her backing band, including Purdy (piano), Matt Gibson (bass), and Mike Harkness (drums). A series of songs recorded with producer John Trainum, including the two-track single "Dreams Before," followed over the next couple of years.
Bollinger returned with her second EP, I Don't Wanna Lose, in 2019. It saw her joined by Trainum on synthesizer and keyboards, Chris Lewis on lead guitar, Jimmy Trussell on bass, and Jacob Grissom on drums, and led to opportunities like opening for Soccer Mommy and touring with Wild Nothing. The following year, Bollinger offered up another EP recorded with Trainum, the self-released A word becomes a sound.
In 2021, Bollinger received an unexpected credit on the title track from Kanye West's Donda, which sampled "Candy" from I Don't Wanna Lose. She soon found herself opening shows for the likes of Jeff Tweedy, Real Estate, and Faye Webster before releasing her fourth EP, Look at It in the Light, on Ghostly International in April 2022. Recorded with Trainum and guests including a string section, it took inspiration from recordings from the 1960s and '70s -- in particular, Beatles demos -- with an aim to illuminate each instrument while allowing for flaws. ~ Marcy Donelson, Rovi