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Flatfoot 56 formed in summer 2000 as a three-piece punk band. The three original members, who are brothers (Tobin Bawinkel, Justin Bawinkel, and Kyle Bawinkel), started writing songs in Fall 2000. By the Christmas season of the same year, they were playing their first concert. In January 2001, the band added Josh Robieson (bagpipes, guitar, mandolin) to the lineup and the band began including the Highland bagpipes and a second guitar into its sound.
In 2001 they recorded their first demo, then in Summer 2002, the band recorded their first full length album, entitled Rumble of 56. This recording was done in Rockford, Illinois, in a studio called the Noise Chamber. Their second album, Waves of War, was released in 2003. Their song, "That's OK," had heavy radio play on stations across the Midwestern United States. It has been known as one of the higher-rated songs Flatfoot 56 has ever played and is definitely a crowd favorite at live performances.
In 2004, Flatfoot 56 performed at the Cornerstone Festival in Illinois for a crowd of about 700 people. It was at this concert that the band released their first album, Knuckles Up. It has been the band's best-selling record, and the group continues to record and tour. The band has been signed to Flicker Records and has re-released Knuckles Up through the label. Their fourth record, Jungle of the Midwest Sea, was released on May 15, 2007.