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Frank Jack
Have you ever heard of Frank Jack? He plays all over Chicago, strangely mostly at open mics. He does something I've never seen before. He usually does a solo show and creates all of his own music, prerecording some of it, but the kicker is he becomes the bizzare characters his songs are about. To find out where he'll be playing next, what I do is I look at different sites that list open mics in chicago. Sometimes they'll post who will be playing, but other times I just call around and ask people if they'll know where he'll be. Trust me, it's well worth it.
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