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Born in the suburbs of Chicago, lead singer Tom Higgenson was originally fascinated with the drums, performing in various pop and rock bands in high school. One of these groups was Harvey's Daughter, where he met bass player Ken Fletcher. The group disbanded but another was re-formed, with Higgenson taking over lead duties as songwriter and singer. Friend and drummer Dave Tirio joined and, in the fall of 1997, the pop-punk group was formed. Plain White T's performed around various Chicago clubs gaining a small but devout following. In the summer of 1999, Higgenson was almost killed in a car accident. The event, which resulted in a ruptured kidney and lacerated lung, gave him a newfound appreciation for life. As a result, the songwriting process grew and the band was being noticed. The group self-released Come on Over in 2001, then jumped to Fearless for the 2002 LP Stop.
Plain White T's struggled with lineup shifts even as they toured heavily in support of the album, but were able to muster up the record All That We Needed, released through Fearless in early 2005. By that point the band's roster had solidified with vocalist Higgenson, Tirio and Tim Lopez on guitar, drummer De'Mar Hamilton, and bassist Mike Retondo. The band next spent time on the 2005 Take Action tour alongside Sugarcult, Head Automatica, and more. They finished out the year touring with Spitalfield, joining up with Motion City Soundtrack in 2006. The enhanced EP Hey There Delilah was released that May; it contained various versions of the popular acoustic ballad "Hey There Delilah" (from All That We Needed), along with four new songs and music videos. Most of the following summer was then spent on Warped Tour before Every Second Counts, their hook-laden major-label debut for Hollywood, appeared in early September. The guys then hit the road on the popular Nintendo Fusion Tour alongside Hawthorne Heights, the Sleeping, and more.