The original members formed as OK Go in 1998 and released two studio albums before Duncan's departure. The band's video for "Here It Goes Again" won a Grammy Award for Best Music Video in 2007. The band are generally known for their unique style of music videos.
The band's lead singer, Damian Kulash, met bassist Tim Nordwind at Interlochen Arts Camp in Traverse City, Michigan when they were 11. Kulash was in for graphic design, Nordwind for music. The band name comes from an art teacher of the band members saying, "OK... Go!" while they were drawing. They kept in touch after camp, often exchanging mixtapes which influenced each other's musical taste and the band's future sound. They met the band's future guitarist and keyboardist Andy Duncan in high school. Nordwind and Duncan moved to Chicago for college, where they formed the band Stanley's Joyful Noise with drummer Dan Konopka. The name OK Go was adopted in 1998, when Kulash moved to Chicago to join the band.
The band plastered the city with posters for its earliest gigs and within a year had shared the stage with international artists such as Elliott Smith, the Promise Ring, the Olivia Tremor Control and Sloan. At the end of 2000, the band was invited by radio host Ira Glass to serve as the house band for live performances of This American Life in Boston, New York, and Chicago.
The band self-released two EPs, titled Brown EP (2000) and Pink EP (2001), which were culled from an album's worth of songs recorded in February 2000 with producer Dave Trumfio, to serve as demos. The early music had electronic influences, as Kulash told the Chicago Reader in 2001, "We were trying to figure out how we could get a sampler and beats to work in rock songs that didn't sound like rip-offs of Portishead." The demos did not land the band a label deal, but got them the attention of booking agent Frank Riley, who offered them shows with They Might Be Giants, a relationship that has endured as OK Go opened for the band numerous times during this period, and was introduced to the band's manager by them.
Though the members of OK Go eventually left for Los Angeles and New York, they consider themselves a Chicago band. In a 2011 interview, Kulash described the band's formative years: “As far as the band is concerned, we only have one home town. We all live in L.A. now but there’s only one period of your life as a band where you’re playing the same clubs every week or every month, and you know everybody in every other band; and it’s all your friends, all the people that work at the clubs, and it’s such a community. Chicago had such a close-knit and intense community five years ago when we were here. It’s amazing. The Empty Bottle was where it all started for us. We played at the Metro and the Double Door as well."