In town: Brad Wenzel and Karl Hess.
In the news: The Late Show on Tuesday celebrates the 20th anniversary of Stephen Colbert’s first appearance on The Daily Show with a reunion. Guests: Jon Stewart, Samantha Bee, John Oliver, Ed Helms, and Rob Corddry. Stephen Colbert is a Northwestern alum and got his start at Second City.
MONDAY, MAY 8
Feminist Happy Hour: We Get it from our Mamas at The Whistler, 2421 N. Milwaukee, 6:00 p.m. Tonight’s show honors Mom and features Le Aboav, Sydney Boyle, Adrienne Brandyburg, Angelica Julia Davila, Deanna Ortiz and Gina Watters.
The Riff at Gallery Cabaret, 2020 N. Oakley, 7:00 p.m. A unique open mic hosted by the kates. Comedians get a last-minute topic and create a four-minute riff.
Is it Still Funny? at The Music Box Theatre, 3733 N. Southport, 7:00 p.m. Is Hal Ashby’s Being There still funny? A screening and discussion with film critic Mark Caro.
I Heart Dick at The Annoyance Theatre, 851 W. Belmont, 8:00 p.m. A special sneak preview of the new series by Jill Soloway (Transparent). The series will not be released until May 12, but you can be the first to see the first two episodes. Jill is an Annoyance Theatre alum.
Brad Wenzel at Zanies, 1548 N. Wells, 8:30 p.m. Tonight and tomorrow night.
Manic Mondays at SLR Bar & Grill, 16409 Halsted, Harvey, 8:00 p.m. Comedy and music hosted by Taneshia Rice and Marilee.
Having it All at iO, 1501 N. Kingsbury, 8:00 p.m. “Stories and improv about being female.” Tonight’s cast includes Ward 43 Alderman Michele Smith.
Best Night Ever at Gman Tavern, 3740 N. Clark, 8:30 p.m. Mike O’Keefe hosts Karl Hess (LA), Blake Burkhart, Lainie Lenertz, Ryan Croft and more TBA.
TUESDAY, MAY 9
Snack Attack Presents Kellye Howard and Sunflower Seeds at Elbo Room, 2871 N. Lincoln Ave., 8:00 p.m. Headliner: Kellye Howard (Last Comic Standing, Second City, OWN Network). Hosted by Prateek Srivastava. Bill Gevirtz, Josh Ejnes and Abi Sanchez.
Chicago Underground Comedy: The ClickHole Invasion at Beat Kitchen, 2100 W. Belmont, 9:00 p.m. The writers and contributors of clickhole.com take over ChUC for one night only.
Winner … of Our Discontent at Second City, 1616 N. Wells, 8:00 p.m. The 105th Mainstage revue. Tickets sell out fast. Check site for additional shows throughout the week.