Showoff was formed in 1997 in Villa Park, Illinois. The band consisted of Chris Envy (a.k.a. Chris Messer/Chris Dalle-Valle) (vocals/guitar), Daniel Castady (drums), Graham Jordan (guitar), and Dave Envy (a.k.a. Dave Hyde) (bass). In 1998, Showoff signed with Maverick Records while it was owned by Madonna. Their self-titled debut album was released the following year in 1999, and was produced by Goldfinger's John Feldmann. The single "Falling Star" reached No. 36 on the Billboard Modern Rock charts that same year.