There may be no braver improviser in Chicago than Susan Messing. In a recent performance she had a hilarious emotional breakdown with her onstage husband, then simulated sex with him—on top of three audience members. Drawing on tremendous acting and voice skills as well as a veritable library of cultural references, Messing creates fully formed characters and has a gift for infusing improvised scenes with a distinct style and tone. Her weekly show at Annoyance, Messing With a Friend, is one of the surest bets for laughs in the city. Open run Thu 10:30 PM, Annoyance Theatre, 4830 N. Broadway, 773-561-4665, theannoyance.com, myspace.com/susanmessing, $5. —Ryan Hubbard
Katie Rich Through 7/22 (with the Frank Hayes 4), Tue 8 PM, $12. Through 7/26 (with the Deltones), Sat 8 PM, $14. Open run (with Carl & the Passions), Wed 8 PM. All at iO, 3541 N. Clark, 773-880-0199, iochicago.net, katierich.com.
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