Once upon a time, there was something called the Red Bar Comedy Club, spun off from the wildly popular local podcast Red Bar Radio. When Red Bar host Mike David and his erstwhile business partner Kyle Lane had a bitter and public falling out, Lane rebranded the club as the Comedy Bar, and it’s still quite successful. But many prominent comedians from the Red Bar orbit (Drew Michael, Danny Kallas, and others) took their acts to Timothy O’Toole’s instead, home of the Wednesday night showcase Comedians You Should Know. If you ask a Chicago comedy connoisseur (or reddit) which local show to check out, CYSK usually comes up first. And while it certainly looks like a frat bar through the windows, Timothy O’Toole’s has a large back room that is about as swanky as an independent comedy venue can get. Up-and-coming star Mike Lebovitz recently recorded his first album there, probably his last major contribution to the scene before he decamps to Los Angeles. But CYSK features many big-shot out-of-town guests, so he’s probably not gone forever.
622 N. Fairbanks, 312.642.0700, comediansyoushouldknow.com
Audience Choice: Zanies, 1548 N. Wells, 312.337.4027, zanies.com
