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Join Anna Caldwell and special guests Carl Chadek, Nikki Krzebiot, Megan Cook, Mary Nora Wolf, and Ross Matsuda for a whimsical cabaret celebrating her 40th birthday and benefiting NAMI Chicago. Through songs and stories, Anna explores what it means to be a middle-aged theater kid, and how entering this phase of life reshapes our dreams, deepens our perspective, and makes us a little more comfortable with life’s unanswered questions.

The evening features an original song Anna wrote with Michael Oldham, an original arrangement with Cody Michael Bradley, and several of her own parodies, alongside songs by Rodgers and Hammerstein, Stephen Sondheim, Jonathan Larson, Lerner and Loewe, Cole Porter, Bock and Harnick, Jerry Herman, Stephen Schwartz, Pasek and Paul, Meredith Willson, Joni Mitchell, the Indigo Girls, and even Mozart.

This show is a fundraiser for NAMI Chicago, which offers free support groups, education and a helpline for people living with mental illness and their families.