Chicago comedy spotlight for Labor Day weekend 2016

An illustrious list of visitors for Labor Day weekend: Paul Mooney, Paul Reiser, Jon Lovitz, Gad Elmaleh, Shang and Nick DiPaolo.

Add the folks coming in for the Funny or Die Oddball Comedy Festival: Jeff Ross, Iliza Shlesinger, Brian Regan, Tony Hinchcliffe, Tom Segura, Donnell Rawlings and returning Chicagoans Cameron Esposito, John Mulaney and Sebastian Maniscalco .

The Roastmaster General is hosting the Festival this year. Which audience members in their fool heads will volunteer to face him on stage this time? Jeff Ross is the Thor of take downs. He is the Superman of smack talk. The Iron Man of insults. The rest of the audience, safely ensconced below, will get to experience the Shazam of schadenfreude. Like he says in  his memoirs, I Only Roast the Ones I Love, it’s all good fun, born of love and affection. But mortals be warned. It’s going to be hella entertaining. Note I’m saying that from over here.

Ticket alert: Aparna Nancherla will be here on September 25, 26 and 27. Each show at a different venue. Visit her web site,,  for tickets and details. Her album, Just Putting It Out There, was released this summer. I recommend following her on Twitter if you don’t already: @aparnapkin. She’s like a very original and witty friend accomplishing the impossible by making life’s vicissitudes, all of it, consistently funny. She is also a writer whose credits include Totally Biased with W. Kamau Bell and Late Night with Seth Myers.

Chicago comedian (now in New York) in the news: Drew Michael’s new album, Funny to Death, will be released on Comedy Central Records this Friday, September 2. It was recorded in Chicago at “Comedians You Should Know.” Comedy Central describes the album as Drew’s unrelentingly honest take on “manifestos to marriage, depression to (not) drinking.”  His companion Comedy Central special (filmed in New Orleans) airs on September 2 at 11:30 p.m. CST.

Please confirm all details before heading out. I’d hate to steer you wrong, especially when it’s right into holiday weekend traffic.

This is just a fraction of comedy events that are taking place around Chicagoland. Check out venues’ full listings and for regular weekly shows, please click on “Comedy each day of the week” above. Thank you to the Chicago comedy community. Thank you to you for reading and helping me spread the word.

Happy Holiday weekend! Wishing you more laughs than labor!


Funny or Die Oddball Comedy Festival at Hollywood Casino Amphitheater, 19100 Ridgeland Ave, Tinley Park, 5:00 p.m. The traveling Lollapalooza of comedy. Chicago line-up is hosted by Jeff Ross. Featuring Cameron Esposito, Sebastian Maniscalco, Brian Regan, John Mulaney, Donnell Rawlings, Iliza Shlesinger, Tom Segura and Tony Hinchcliffe. If you’re looking for a great read, Jeff Ross’s I Only Roast the Ones I Love is one of the best comedy memoirs I’ve ever read.

The Chicagoans:


The Interview Show at The Hideout, 1354 W. Wabansia, 6:30 p.m. Mark Bazer’s guests tonight are humor writer and author Amy Krouse Rosenthal, chefs Erling Wu-Bower (Nico Osteria) and Cosmo Goss (Publican), sports reporter Julie DiCaro and musician Robbie Fulks.

Chicago Fringe Festival at various locations, 7:00 p.m. Performances at five different Jefferson Park locations (all within walking distance) through September 11. Follow link for complete schedule. Shows are from 7–11 pm on weekdays and from 1 pm–11 pm on weekends and Labor Day. Here is a list of the Festival’s comedy shows.

Jon Lovitz at The Improv, Woodfield Mall, Schaumburg, 8:00 p.m. Well, hellllo! Jon Lovitz got his comedy start with the Groundlings and went on to SNL where his forever memorable characters included Tommy Flanagan of Pathological Liars Anonymous, Hannukah Harry and Master Thespian.  His film work includes Big, A League of Their Own, The Wedding Singer, High School High, Small Time Crooks, and Rat Race. He will be at the Improv through Sunday. Follow link for all show times.

Paul Reiser at City Winery, 1200 W. Randolph, 7:30 p.m. and 10:00 p.m. The star of Mad About You and My Two Dads has also appeared on Curb Your Enthusiasm and in the films Diner, Beverly Hills Cop I and II, Aliens, The Marrying Man and Bye Bye Love. He is the bestselling author of  Couplehood, Babyhood and Familyhood. He recently released How to Get to Carnegie Hall. He is also currently starring in Steven Soderbergh’s Red Oaks, the hit series on Amazon, in which by the way, Chicago’s (now L.A.’s) Beth Stelling guest stars.


EbonyEssenceJet: The So What? Issue at The Revival, 1160 E. 55th St., 8:00 p.m. EbonyEssenceJet is the all-female sketch and comedy revue featuring Ashley Bland, Briane Goodrum, Kimberly Banks and Salesha Mason.

The Lincoln Lodge presents CJ Sullivan at Subterranean, 2011 W. North Ave., 8:00 p.m. The Lincoln Lodge returns with its 17th season! The Lincoln Lodge helped to launch comedians like Cameron Esposito, Hannibal Buress and TJ Miller. Dedicated to making comedy available to everyone. You decide what to pay. Headliner: CJ Sullivan as he gets ready to record his album and depart for L.A.

Drink Date Laugh at The Laugh Factory, 3175 N. Broadway, 8:00 p.m. Hosted by Paul Farahvar. “We are bad at dating and so can you!” Comedians share their most embarrassing, hellish and funniest relationship stories. Audience members will have a chance to do the same and to win prizes. Featuring Andrew Sitter, Ross Kelly, Marty DeRosa and more TBA.

Word Play at The Revival, 1160 E. 55th St., 8:00 p.m. Hip hop, spoken word and stand-up curated by Dave Jeff and hosted by comedian, radio personality and Windy City Live guest host, Leon Rogers.

The Great Show with Danny Catlow at The Annoyance Theatre, 951 W. Belmont, 8:30 p.m. Guests range from real-life Chicagoans to made-up characters. A new topic each week through September 30. Tonight: Dark Arts.

Friday Night Fudge at iO, 1501 N. Kingsbury, 8:30 p.m. Friday Night Fudge has moved to iO and this is its first night in its new home. Fudge is Damian Anaya, Tim Lyons, Vince Portacci, and Dan White. The evening is half-music, half-comedy. Rotating iO house teams present The Harold. No two shows the same.

Shang at Zanies, 1548 N. Wells, 8:30 and 10:30 p.m. Shang will be at Zanies downtown through Sunday. Follow link for all show times. Shang’s stage and television appearances are worldwide, including shows in Ireland, England, Japan and the Netherlands and in the U.S. on NCISZack and CodyPolitically Incorrect and The Jamie Foxx Show. His album Shangry is one of XM radio’s most popular. Check out his site for his thoughts on this year’s political insanity.

I Hate Everyone But Us at Flat Iron Comedy, 1579 N. Milwaukee, 9:00 p.m. A work by some of Second City’s best: Julia DiFerdinando, Shantira Jackson and Rachael Mason. Suggested donation: $10. Pay what you can.

The Time is Now at Under the Gun Theater, 956 W. Newport, 9:00 p.m. Through September 30. A comedy revue asking what would happen if we really carpe’d the diem.

Funked Up Friday at The Laugh Factory, 3175 N. Broadway, 10:00 p.m. Finish the week and start the weekend with this party hosted by AJ Lubecker. (Interview here.) Featuring Marty DeRosa, Chris Bader, Martin Morrow, Kristen Lundberg.

The Holy Fuck Comedy Comedy Hour at The Annoyance Theatre, 951 W. Belmont, 11:59 p.m. This is an opportunity to see a free show at The Annoyance with some of the theater’s top performers. New material written every week. The word the Annoyance uses is “eclectic.” Or did they say electric? Betcha it’s both.



Chicago Fringe Festival at various locations, 1:00 p.m. Performances at five different Jefferson Park locations (all within walking distance) through September 11. Follow link for complete schedule. Shows are from 7–11 pm on weekdays and from 1 pm–11 pm on weekends and Labor Day. Festival comedy shows here.

Late Late Breakfast’s 3.5 Year Punniversary at The Hideout, 1354 W. Wabansia, 3:00 p.m. Free performance, puns, party and pancakes.

Paul Mooney LIVE in Chicago at the Harold Washington Cultural Center, 4701 S. Martin Luther King Dr., 7:00 p.m. A live taping and historic opportunity to see one of the country’s most influential comedians.

Paul Mooney’s early gigs included writing for Richard Pryor (they became best friends), for Redd Foxx on Sanford and Son and for Good Times. He also wrote for In Living Color and was head writer of The Dave Chappelle Show. Movies he appeared in include Which Way is Up?, Bustin’ Loose, The Buddy Holly Story where he played Sam Cooke and too many more to list.

He is an uncompromising truth-teller on social issues and racism and has had many TV appearances heavily edited because he has some strong stuff to tell, but his comedy is always the way he sees it and never less.

Paul Mooney has influenced countless straight-shooting comedians from Richard Pryor to Sandra Bernhard to Robin Williams to George Lopez to Hari Kondabolu. Just an extremely long list.

He published his memoirs, Black is the New White in 2009. He turned 75 in August. One writer recently raised questions about his health and ability to tour. You can read a reprint of that article here. But that article was controversial in itself. Rebuttals here and here.

In any case, if you can get tickets, the evening promises to be an unforgettable experience with a comedy legend who has a lot more to say.


Playground Drag Race at The Playground Theater, 3209 N. Halsted, 7:30 p.m. Hosted by celebrity drag queen Pam Who?, this comedy lip-synching event benefits LGBTQ organization, The Center on Halsted. Contestants: Alessandra Drapos, Diego Sanchez, Eric Simon, Jamie Meun, Jessi Realzola, Maureen Monahan, Michelle Mestas, Tiff Svitko, Tony Orlando, and Yazmin Ramos.

No Guts, No Story at Second City, 1616 N. Wells, 7:30 p.m. Last night! Sketch comedy written by and based on the experiences of  the all-veterans cast of “Stars and Gripes”: Crystal Clark (Army), Tyler Decker (Army), Cam Dupre (Marine Corps), Landis Frederick (Navy), Melissa Patterson (Air Force), and Jonah Saesan (Marine Corps).

Cupid Has a Heart On at Stage 773, 1225 W. Belmont, 8:00 p.m. Chicago’s longest running musical comedy is a sketch show about body image, love, relationships and the way they haunt us. Created by Chicago comedy guru Brian Posen who is also Stage 773’s creative director. He directs the play and provides the musical accompaniment. This production has toured nationwide and its music has been featured on NBC, ABC, WGN, WTTW, WCKG and WBEZ. Every Saturday.

Shark Showcase at Café Latino, 1454 W 18th St, 8:00 p.m. Tonight: Antonio Aguilar, Kristin Ryan, Blake Burkhart, Laura Hugg and hosted by Noah Gutierrez. This showcase is produced by Noah Gutierrez, Ben Flores, Kristin Fenchak and Carly Kane.

Nick DiPaolo at Thalia Hall, 1807 S. Allport, 8:30 p.m. Among his many credits, Nick DiPaolo is an Emmy-nominated writer for his work on HBO’s Chris Rock Show and also was one of the stars of the Inside Amy Schumer sketch, “Twelve Angry Men” where a jury debated whether Amy Schumer is “hot enough to appear on TV.” UPDATE: Show cancelled. 



Chicago Fringe Festival at various locations, 1:00 p.m. Performances at five different Jefferson Park locations (all within walking distance) through September 11. Follow link for complete schedule. Shows are from 7–11 pm on weekdays and from 1 pm–11 pm on weekends and Labor Day. A list of the Festival’s comedy shows here.

Improv Nerd at Second City, 1616 N. Wells, 5:30 p.m. A behind-the-scenes in-depth look at what improvisers are really thinking. A wealth of insight and honesty and I don’t just mean the happy stuff. Expect true discussions you won’t hear anywhere else about anger, shame and insecurity and how they fit into life and comedy, all the ups and all the downs. Then you get to watch a scene with award-winning improv pro Jimmy Carrane and his guest. This week it’s Micah Philbrook of the tim&micah project who is also a Second City faculty member and a founder of pH Productions. Catch up on past Improv Nerd shows here and I also recommend Jimmy’s blog.

The tim&micah project:


Comedy Cruise at Navy Pier, 7:00 p.m. Sail into fall! Headliner: Brandi Denise. Featuring Em Brown and Paul Farahvar. Hosted by Darren Georgia. Includes buffet.

Jew-si-can: Diviersity Uncorked at Second City, 1616 N. Wells, 8:00 p.m. “A sketch show about the life adventures of a Jewish guy and a Mexican lady. Jew-Si-Can celebrates cultural differences and finds the similarities that came to bond an unorthodox friendship between a Jewish senior citizen and a Mexican young woman.”

Arguments and Grievances at @North, 1637 W. North, 8:00 p.m. The debates everyone would rather watch. Named a “Best of Chicago Variety Show” by Chicago magazine. Tonight: Stephanie Hasz vs Nicholas Rouley (You’re Crazy vs No You’re Crazy), Tim McLaughlin vs Geoffrey Asmus (Alpha vs Beta), Dan Sheehan vs Stephanie Weber (Utopia vs Zootopia), Nicky Martin vs Tyler Jackson (Stay at home Dad vs Working Dad).

Gad Elmaleh at Thalia Hall, 1807 S. Allport, 8:30 p.m. One of France’s biggest comedy stars. Gad Elmaleh is a French Jewish comedian who grew up in Morocco. He speaks French, Hebrew, Arabic and English. He is also a stage and movie actor. He has appeared in numerous French movies (waayyyy too many to list) and also in Woody Allen’s Midnight in Paris and Steven Spielberg’s The Adventures of Tintin. He has been called “the French Jerry Seinfeld,” and actually played Jerry Seinfeld’s role in the French version of Bee Movie. France’s Ministry of Culture awarded him the “Chevalier des Arts et des Lettres” in 2006 and he was also voted “The Funniest Person in France.”



Chicago Fringe Festival at various locations, 1:00 p.m. Performances at five different Jefferson Park locations (all within walking distance) through September 11. Follow link for complete schedule. Shows are from 7–11 pm on weekdays and from 1 pm–11 pm on weekends and Labor Day. A list of the Festival’s comedy shows here.

The Riff at Gallery Cabaret, 2020 N. Oakley, 7:00 p.m. So many great things about this open mic. It’s hosted by the kates! Tonight it’s kates cast members Soli Santos and Amy Sumpter with a special appearance by Elizabeth Gomez. Also: comedians draw a topic on the spot and have four minutes to work it out. Some comedy magic happening for sure.

Back2School at iO, 1501 N. Kingsbury, 8:00 p.m. Prepare for the upcoming school year. Improv teams figure out what to with mystery supplies in a back-to-school backpack. With BOMBSHELL, FAKE and Lady Crush.

Improv All-Stars at Second City, 1616 N. Wells, 8:00 p.m. All-star cast and director. Cast: Ryan Archibald, Brooke Breit, Brendan Dowling, Peter Kim, Kelsey Kinney, Julie Marchiano, Rachael Mason, Abby McEnany,Rachel Miller, Scott Morehead, Adam Peacock, Dana Quercioli, John Sabine, Adam Schreck, Kevin Sciretta and Jamison Webb. Directed by Mick Napier.

Best of the Second City at Second City, 1616 N. Wells, 8:00 p.m. Second City’s greatest hits over its 52-year history.

CAMP: A Play-bor Day Comedy Show at Field Trip, 8:00 p.m. Message for special backyard location. Free show. Donations appreciated. Hosted by Tessa Orzech and Samantha Berkman. Featuring Zach Frey, Lydia House, Josh Ejnes, Ben Banach, Samantha Berkman, Carly Ballerini, Cameron Gillette, Brandon Kieffer, Jeff Arcuri and Jeff Scheen.

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