Dewees graduated from Liberty High School in Liberty, Missouri in 1994. He started college at William Jewell College in Liberty later transferring to the University of Missouri to study music composition. In 1995, he was asked to replace Sean Ingram as vocalist for the Kansas City hardcore band Coalesce. This angered Ingram, and caused a fight that eventually broke the band up. However, in the summer of 1996, the band decided to re-form, but this time with James Dewees as a drummer. With them, he recorded the band's first two full-length albums Give Them Rope and Functioning on Impatience. Dewees was later kicked out of college for missing too many classes while touring with the band.
In 1997, Coalesce played a music festival in Wilkes-Barre, Pennsylvania with fellow Kansas-Citians The Get Up Kids. At the end of Coalesce's set, they began smashing all of their equipment, and James picked up his Floor tom and threw it into the audience, hitting a girl on the head. Someone picked it up and tried to steal it, so James began chasing him, along with The Get Up Kids' guitarist Jim Suptic. They started talking, and Suptic invited James to hang out with the rest of the band.
Coalesce and The Get Up Kids began collaborating more and more, playing shows together and eventually covering each other's songs for a split 7-inch. James recorded keyboard for the band on their Red Letter Day EP, and after its release, joined the band full-time. After the release of the band's second album Something to Write Home About, The Get Up Kids began receiving much greater national attention. In order to capitalize off of the success of Something to Write Home About, as well as bridge the gap between their next album, the band released a collection of B-sides and rarities, entitled Eudora, in 2000. This also included a re-make of "A Newfound Interest in Massachusetts", with a new arrangement placing a much heavier emphasis on the piano.

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