Based near Annapolis, Maryland, Hollowed Sky formed in 2016. Berchielli, Bradshaw, and Rupertus were coming off extended musical hiatuses after their previous projects had fizzled out, and they were looking for a place to jam. Within 30 seconds of their first jam session, they knew they were onto something special. As they continued to play, their jams began to take shape, and several months later, they realized they needed a vocalist.

Jay Orem joined the band in 2017 and remained the vocalist until 2022. After several months of composing new music as a trio, Robyn Bingham joined the band in 2023 to add her vocals and lyrics.

In 2023, Hollowed Sky released their first single with the new lineup, “Kill My Darlings,” followed by “Hookworm.” In 2024, they released “The Northern Lights” and a cover of Michael Jackson’s “Beat It.” Their latest single, “Patchwork Beast,” was also released in 2024.