38. Remy Bumppo

Location: 3717 North Ravenswood Ave.
Website: remybumppo.org

Named after the founder's pet cat and dog, the award-winning Remy (cat) Bumppo (dog) theater aims to both stir the heart and make you think—all that in an environment more intimate than you'd find in the downtown theater district.

Their current season is explicitly political, with plays that draw on the Civil War and the Civil Rights Movement. Oh, and there's even a play about kidnapping the dog of conservative Senator. These people aren't afraid to step on some toes in the name of art (and civil disobedience).