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In late 90's Chicago, Mills rose to local prominence through collaborations with Mekons Jon Langford and Sally Timms, and on bills with acts like Steve Earle, Wilco, Neko Case, My Morning Jacket et. al. But while many would find comfort solely mining the rich soil of Americana music en vogue at the time, Mills was never completely at home within the genres somewhat narrow confines - perhaps first evidenced on tracks like "Signal/Noise", the closing number on 2000's Kiss It Goodbye, a post-modern homage to Phil Spector's wall of sound masterminded by producer Brian Deck (Modest Mouse, Josh Ritter, Iron and Wine).

Over the next decade Mills would travel constantly throughout the United States and Europe, developing a loyal following and touring with artists including Ben Folds, Andrew Bird, Califone, Bishop Allen, The Handsome Family, and Lucero.