Sherry had a productive 2019, releasing the Vacant Lands EP, full-length album Western Sky, and playing dozens of shows around Southern California including a record release show at the Hotel Cafe. Stars, a single included on​ both releases of 2019 and 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, signing with a new record label L.A. Tangerine and 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. 

"My interest in music started at a young age. My Dad has an extensive record collection, it's something I always loved going through. At that age, I was just picking out the albums that I thought looked the coolest. With that said, playing instruments was always encouraged in my home."