Huntington Beach based Reel Big Fish were one of the more successful bands to emerge in the third-wave ska explosion of 1997. The ska-punk act formed in Huntinton Beach as a trio consisting of vocalist/guitarist Aaron Barrett, bassist Matt Wong and drummer Andrew Gonzales. This early incarnation of the band played mostly party-ready rock, a quasi-ironic hair-metal influence that would show throughout the band's career. Reel Big Fish soon developed into a ska act, going through many early horn players before solidifying with Scott Klopfenstein (trumpet, vocals), Grant Barry (trombone) and Dan Regan (trombone) and Tavis Werts (trumpet). The band recorded and self-released their debut Everything Sucks in 1995.

Everything Sucks' underground success landed the band a deal with indie Mojo Records, which by 1996 became a joint venture with Universal. Mojo president Jay Rifkin and former Oingo Boingo bassist John Avila co-produced Reel Big Fish's breakthrough Turn the Radio Off. The 1996 release broke into the mainstream through the success of the single "Sell Out." By the summer of 1997 Turn the Radio Off was one of several records to pull ska music into the American mainstream. Why Do They Rock So Hard? followed in 1998.

"Sell Out" would prove to be the thematic template for the band's future work, as an increasingly cynical view of the music industry continued to emerge through Barrett's lyrics. The mainstream's interest in ska music quickly evaporated and the band's ambitions were suddenly shackled to an out of style genre. Reel Big Fish found themselves trapped by their record deal as well, as Mojo was sold to Zomba/Jive Records in 2000. Jive, better known for prefabricated boy bands, would prove to be an awkward home for the Mojo acts. It would be nearly five years before Cheer Up! emerged from Jive, and another three before 2005's We're Not Happy 'Til You're Not Happy. Rumors of the label micromanaging the band's sound persisted, fueled by very radio-friendly and decidedly ska-free singles from the releases. If it was any indication, the band's embittered cynicism towards the process became their predominant lyrical theme.

As of January 2006 the band found themselves free of a major label contract for the first time in more than a decade.