Kansas City Lightning: The Rise and Times of Charlie Parker by Stanley Crouch (2013) — A biography of Charlie Parker's Kansas City years, from his childhood in the 12th Street neighbourhood through his education in the city's jazz clubs. Crouch captures the musical world that shaped one of the great figures in American music. Read it before visiting 18th and Vine.
The Pendergast Machine by Lyle Dorsett (1968) — The definitive account of Boss Tom Pendergast, the political machine that ran Kansas City for decades and made it a wide-open town where jazz flourished and prohibition was ignored. Essential context for understanding the city's history.
In Cold Blood by Truman Capote (1966) — Not set in Kansas City, but Capote's account of the 1959 murders of the Clutter family in rural Kansas captures the stark Kansas landscape that surrounds the metro area. The book's cold-eyed precision is a good antidote to Midwestern boosterism.
American Royal by Thomas Frank (2004) — Frank's What's the Matter with Kansas? examines why working-class Kansans vote against their economic interests, using the region's political culture as a lens for understanding modern American conservatism. Sharp, essential, and relevant.