Sherry had a productive 2019, self-recording and releasing his album Western Sky and playing dozens of shows around Southern California, including a record release show at the Hotel Cafe. Stars, the lead single from Western Sky, co-written with Misty Boyce, found itself in rotation on college radio stations across the U.S.

2020 brought a new chapter despite everything in-person coming to a halt. Sherry signed with a new record label, L.A. Tangerine, becoming the first artist on their roster with the releases of Run / Five Horsemen and Stars ft. The Green Flamingos.

In 2021, singles This Too Won't Last and Flying Colours both debuted on KCSN, L.A.'s leading radio station for independent music.