Forming in 1997, Chicago's Showoff comprised vocalist/guitarist Chris Envy (aka Chris Messer), bassist Dave Envy, drummer Dan Castady, and guitarist Graham Jordan. The punk-pop group released their self-titled debut album, which was produced by Goldfinger's John Feldmann, in 1999 on Maverick. Touring around with bands like the RX Bandits, Everclear, Allister, Citizen King, and Student Rick, among others, the band also recorded their sophomore album with Mark Trombino before being dropped by Maverick (ultimately causing the record to go unreleased) and breaking up in 2002. Members went on to form the pop/rock outfit the Fold and Farewell My Enemy. Showoff re-formed in late 2005 with a new lineup consisting of founding member Chris Envy, along with guitarist Nate Envy (aka Nate Thruman), drummer Mickey Molinari, and bassist Carl Kusch.