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Tony Kushner and Jeanine Tesori's Caroline, or Change premiered on Broadway on May 2, 2004. A serious and challenging musical set in Louisiana at the time of President Kennedy's assassination, it played only 136 performances while competing against the more upbeat likes of Wicked and Avenue Q (both of which are still running). The cast included leading lady Tonya Pinkins and supporting player Aisha de Haas--both former Chicagoans and Columbia College alumnae. (Full disclosure: I teach at Columbia.)
Check out my Reader review of Court Theatre's Chicago premiere production.