Members of two alternative San Francisco bands, the Thrill Pillows and Honeypot, formed Blue Sky Roadster in early 1997 after their bands broke up. They drew influences from power pop bands such as Redd Kross, the Posies, and Teenage Fanclub. Three different Blue Sky Roadster songs appeared on two industry compilation CDs that were released in May of 1997. The first, a Popsmear Records compilation of San Francisco bands, was distributed and played on college radio stations. The second was BAM Magazine's Slushee CD. Blue Sky Roadster released their first album, the seven-song EP Magnificent Seven Social Club, in 1997. It was followed by the five-song EP Julio's Dream in 1998. Blue Sky Roadster released their first full-length LP in 2000, Roller Coaster Goodbye. In August of 2000, Blue Sky Roadster appeared on Break Through, a VH1 show featuring "undiscovered" bands.