Chicago comedy spotlight for Monday, April 23-Sunday, April 29, 2018

Visitors in town: Stephen Tobolowsky, Patton Oswalt, Raanan Hershberg, Jonah Ray, and Kathleen Madigan.

At the Improv: The Kates! Also, Jim Belushi and the Board of Comedy, and Ken Garr.  At Zanies: Chris Kattan and Friends, Jared Freid, Larry Reeb, Alex Edelman, and Vince Maranto.

Ticket Alerts:

May 5 and 6: Doug Benson at Zanies

May 7: Armando Diaz Experience at iO with special guest Svengoolie.

May 11: Funny Ha-Ha at The Hideout with Julia Sweeney, Lily Be, Cassie Walker Burke, Elizabeth Gomez, Jennon Bell Hoffman, Megan Stielstra, Steve Delahoyde and Claire Zulkey. 

May 12: Rita Rudner at the Raue Center

Following is this week’s spotlight. Please confirm all details!


Benefits of Laughter Variety Show at Playground Theater, 3209 N. Halsted, 8:00 p.m. Proceeds benefit Lurie Children’s Hospital.

Stephen Tobolowsky at Max & Benny’s, 461 Waukegan Rd., Northbrook, 7:00 p.m. The author and prolific character actor (The Goldbergs, Silicon Valley, One Day At a Time) talks about his latest book, My Adventures with God. He will be at The Standard Club on Tuesday morning.

The Armando Diaz Experience at iO, 1501 N. Kingsbury, 8:00 p.m. This classic weekly iO show has some great evenings planned tonight and ahead. Tonight: Alicia Swiz, the creator of Slut Talk and Feminist Happy Hour who is also a professor, writer, and comedian.



Comedy Cocktail at House of Blues’ Foundation Room, 329 N. Dearborn, 6:00 p.m. Produced by James Allen Kamp, creator of the most excellent DJ Tone-Knee kicks off the evening at 6:00 p.m. Stand-up showcases at 7:30 p.m. and 9:00 p.m. RSVP for free admission. Early arrival recommended. Seats go fast! Always a stellar, diverse line-up of Chicago’s top comedians and surprise drop-ins.

7:30 p.m. Host: Mickey Housely. Featuring Prateek Srivastava and Chris Trani. Headliner: Marty DeRosa

9:00 p.m. Host: Joe Kilgallon. Featuring Tim Smith and Derek Smith. Headliner: Taneshia Rice

Patton Oswalt at Community Christian Church, Naperville, 7:00 p.m. Patton Oswalt and Gillian Flynn discuss I’ll Be Gone in the Dark, the book his wife Michelle McNamara was working on at the time of her death. Sponsored by Anderson’s Bookshop.

Julia Sweeney: Older and Wider at Second City, 1616 N. Wells, 8:00 p.m. Sit in the living room of a favorite Saturday Night Live alum while she tells you the best stories of her post-SNL life. Well, it’s not actually Julia Sweeney’s living room, but she has a knack for connecting with audiences and making any venue feel like home. The evening is about her ups and downs, relationships, parenting, and what it’s like to be famous and then fit back into every-day life on the North Shore (in Wilmette). Don’t miss!  Most Tuesdays, Wednesdays and Sundays through May. Follow link for all show times. This show consistently sold out in workshopping mode earlier this year, so get tickets soon!



The Not That Late Show at Under the Gun Theatre, 956 W. Newport, 8:00 p.m. With Mesha Arant, Nate Fleming, and special guest Sameena Mustafa. Hosted by Justin Swinson.

Comedians You Should Know at Timothy O’Toole’s, 622 N. Fairbanks Ct., 9:30 p.m. Nationally renowned stand-up showcase. Blake Burkhart hosts Rob Mailloux, Jonah Jurkens, Allison Dunne, Marty DeRosa, Erica Clark, and Raanan Hershberg.


Improvisexation at The Annoyance Theatre, 851 W. Belmont, 9:30 p.m. “Come see the show that’s banned in three-quarters of the world.”



The Kates at The Improv, Woodfield Mall, Schaumburg, 7:30 p.m. The ultra-talented all-women stand-up showcase created and produced by Kelsie Huff. Always an unforgettable evening of diverse comic voices. Tonight: Kelsie Huff, Amy Sumpter, Erica Nicole Clark, Jan Slavin, Gwen LaRoka, and Erica Watson.

How’d We Get Here? at Bourbon on Division, 2050 W. Division, 8:00 p.m. “Gut-wrenching, tear-jerking stories from some of Chicago’s hottest comedians.” Tonight’s theme is “Fool Me Twice,” all about making the same mistake twice. Storytellers: Adrienne Brandyburg, Kellye Howard, Whitney Wasson, and Zako Ryan.

Damon Williams at The Promontory, 5311 S. Lake Park Ave. West 7:30 p.m. and 10:00 p.m. Showcase hosted by Eli Hamilton. Tonight’s theme is “nostalgia.” Headliner: Damon Williams is a Chicagoan, Windy City Live guest host and has been featured on BET. He hosted Showtime at the Apollo, has his own Comedy Central special and opened for the Kings of Comedy. He also has one of the most interesting backstories in comedy. You can hear him talk about it here.

Sinbad at Space, 1245 Chicago Ave., Evanston, 7:00 p.m. Sinbad sits in with the Victor Wooten trio for a night of music and comedy. Interesting fact: Sinbad’s born name is David Adkins. He became “Sinbad” in tribute to Sinbad the Sailor. Early in his career, he beat Dennis Miller on Star Search, but ultimately lost to John Kassir (Tales from the Crypt).



20×2 at Schubas, 3159 N. Southport, 7:00 p.m. Twenty creative people get two minutes to answer one question. Tonight’s question: where do we start? Comic and serious.

Jonah Ray at @North Bar, 1637 W. North Ave., 8:00 p.m. and 10:00 p.m. Jonah Ray’s “Festival of Me” is tonight and Saturday night. Jonah Ray co-hosted The Meltdown with Kumail Nanjiani, The Nerdist Podcast with Chris Hardwick, and Mystery Science Theater 3000. His podcast is Jonah Raydio.

8:00 p.m. Stand-up show

10:00 p.m. Live movie riffing



Kathleen Madigan at the North Shore Center for Performing Arts, 9501 Skokie Blvd., Skokie, 8:00 p.m. Kathleen Madigan is an internationally touring headliner. Lewis Black said she is “the funniest comic in America, bar none.”


Jonah Ray at @North Bar, 1637 W. North Ave., 8:00 p.m. and 10:00 p.m. The last night of Jonah Ray’s “Festival of Me.”

8:00 p.m. Stand-up show

10:00 p.m. Jonah Raydio live recording

Faded at The Revival, 1160 E 55th St., 9:30 p .m. Comedy showcase by T. Murph (Kevin Hart’s The Next Level, Epix’ Get Shorty, Key & Peele).



Everyone’s A Lawyer at Laugh Factory, 3175 N. Broadway, 7:00 p.m. Comedians turn lawyer for an evening. Laugh AND pick up useful arguing skills. Given the times, those skills will probably come in handy immediately. Created and hosted by comedian and lawyer Paul Farahvar.

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