Your Chicago comedy calendar for December 28-January 3

The biggest lesson I learned about Chicago comedy in 2015: get on the Twitter Train (and try saying that fast when you’re explaining it to people). Main reason, you’ll catch a lot of pop-up quickly sold-out shows.

Aziz Ansari and Hannibal Buress each tweeted a series of spontaneous Chicago shows in 2015. This Christmas Eve, Amy Schumer and John Mulaney were surprise Santas when they used Twitter to announce a last-minute show at Constellation on Western Ave. Then they did it again the day after Christmas. Both shows sold out within minutes. Only way to catch them was to be in the right place (Twitter) at the right time.

Especially be on the look-out around holidays when Chicagoans come home (or visit Chicago relatives, ie. Amy Schumer whose brother lives here). The weeks immediately before tapings are another auspicious time because Chicagoans often come home to test their material. Follow your favorite comedians on Twitter, especially the ones with Windy City connections. You could be rewarded with an unexpected gift.

More recent finds: a Vocalo interview on the show Council of Feminist Thought with two of our star stand-ups, Natalie Jose and Kristen Toomey.

I also loved this interview with another Chicago all-star, Damon Williams. He is a national headliner, member of the Kings of Comedy tour and one of the funniest guest hosts on Windy City Live. This interview is one of the most honest I’ve ever heard. He talks about growing up in Chicago, early work in the drug trade and leaving it behind, fatherhood, Chicago comedy and working with game-changers like Bernie Mac and Chris Rock. Added cool fact: the radio host conducting the interview is his son.

This is another fabulous week in Chicago comedy. Visitors include John Oliver, Adam Ferrara and Jessimae Peluso. The fantastic Chicagoans returning home include Michael Palascak, Ron Funches and ‘Lil Rel’ Howery.

The out-of-this-world showcases continue. Check out the 42-star line-up at The Two Hour Comedy Hour on Saturday. Mike Cronin, co-producer of Monday’s Best Night Ever showcase kindly spoke with me here about putting together a showcase and what makes them so special and unique. (He’s also got some tips about surviving holiday parties. We’re not out of those woods yet.)

A relaxing way to fend off anticipatory stress, coast through your commute and ease into the New Year’s first work week: Chicago’s Comedy Scene Radio is back from break! From 7:30 a.m. – 9:00 a.m., meet up and laugh with hosts Tony Carr and Steve Touhy. They’ll come to you when you tune in online here or download the app!

UPDATE 12/29: This just in! Dobie Maxwell has arranged a special event with nationally acclaimed comedian Tom Dreesen at The Laugh Factory on Saturday, January 16 at 1:00 p.m. The seminar, “The Joy of Standup Comedy and How to Get There” is free, but reservations are required due to limited seating. The hour is “designed for those in the entertainment field as stand ups, writers, producers, actors, or anyone who just simply wants to enjoy their journey in life.” To reserve your spot, email Dobie at or call (312) 692-9915. Wow. Highly, highly recommend!

This is both my last post of 2015 and the first of 2016! Thank you to everyone who read “Comedians Defying Gravity” this year. As always, if you have a show to add, please email me at When something catches your eye here, check out that venue’s entire schedule. I’ve listed only a fraction of our city’s beautiful comedy universe.

Please confirm all details before heading out into this “wintry mix.” What a ridiculous euphemism. As if it’s a fucking snack mix! It’s an icy, treacherous pit of monochrome despair. But anyway … warm comedy makes great winter therapy. By the way, New Year’s Eve is so jam-packed, I’ve got a separate post for it here. But see below for the rest of the week which has just as much to celebrate.



“Sadsacks and Wisecracks” at High Hat Club, 1920 W. Irving Park Rd., 8:00 p.m. Weekly comedy showcase hosted by Natalie Jose. Natalie is a cast member of Chicago Underground Comedy, starred in the OWN network’s My Life is a Joke and was featured on Last Comic Standing this past summer. Tonight Natalie hosts Denise Ramsden, Kristen Lundberg, Langston Kerman, J. Michael Osborne and Kristen Studard. With music by Kate Adams.


“Best Night Ever” at the GMan Tavern, 3740 N. Clark, 8:00 p.m. Free showcase produced by Mike Cronin, Sam McHale, Thomas Brady and Dave Losso. Tonight Dave Losso hosts Max Friedman, Cleveland Anderson, Shannon Noll, Josh Branham, Tommy McNamara, Langston Kerman, Sammy Arechar, Calvin Evans.

“The WRIPT/HERALDO” at iO, 1501 N. Kingsbury, 8:00 p.m. Team Heraldo performs long-form improv in Spanish for English speakers. Tonight WRIPT joins Heraldo.

“The Armando Diaz Experience” at iO, 1501 N. Kingsbury, 8:00 p.m. Chicago’s longest running improv show founded by Adam McKay (Anchorman, Talladega Nights), Dave Koechner (Anchorman, Thank You For Not Smoking, SNL) and the actual Armando Diaz (founder of the Magnet Theater in New York). This iconic Chicago comedy experience is a two-act long-form show where one person’s personal stories become fodder for the improv team.

House of Stuart presents “(Sub)Urban Fervor” at MCL Chicago, 3110 N. Sheffield, 8:00 p.m. Entertainment from the city and suburbs.

“Wild Out Mondays” at SLR Bar & Grill, 16409 S. Halsted, Harvey, 9:00 p.m. Improv, stand up and music hosted by Just Nesh. Tonight: offensive t-shirt party.

“The Mixer” at The Playground Theater, 3209 N. Halsted, 10:00 p.m.  “The Mixer is a show Monday nights where everyone who shows up gets to play! Each week starting at 10pm we have a workshop from some of the top performers and coaches in Chicago. At 10:30pm we break into teams and run a long form show. Hosted by Kevin Reader and Bryan Duff of Lumberjack Tsunami, The Mixer is for anyone interested in improv whether you’re brand new or old hat.”

The Second City’s “Holidazed and Confused” Revue at Second City, 1616 N. Wells. 11:00 p.m. Tonight’s earlier show is sold out.



“Comedy Cocktail” at House of Blues, 329 N. Dearborn, 7:00 p.m. No cover. Comedy showcase at House of Blues’ VIP lounge, The Foundation Room (4th floor). Presented by Tonight: Ricky Gonzalez, Abi Sanchez and Jonah Jurkens. To RSVP, call (312) 923-7050 or (312) 923-2035 after 6:00pm.

Ron Funches at Zanies, 1548 N. Wells, 7:30 p.m. and 9:30 p.m. Ron Funches is the popular star of NBC’s Undateable and a regular on Comedy Central’s Kroll Show.

“Michael Palascak” at Zanies, 5437 Park Place, Rosemont, 8:00 p.m. Michael Palascak has appeared on just about every late night show, including with Jay Leno and Dave Letterman and this past summer was a top finalist on Last Comic Standing.

Jessimae Peluso at Zanies, Pheasant Run Resort, 4051 East Main St., St. Charles, 8:00 p.m. Jessimae Peluso is the star of MTV’s Girl Code.

“Potential Boyfriends” at MCL Chicago, 3110 N. Sheffield, 8:00 p.m. “Potential Boyfriends is a long form improv group formed by a bunch of guys with little to no interest in committing to anything substantial anytime soon.” With Peter Corey, Pat Ivansek, Nick Johnson, and Joey Lesiak.

“The Laser Comedy Variety Show” at Stage 772, 1225 W. Belmont, 8:00 p.m. Fast moving laser art morphs into characters accompanied by music and voiceover. Created and performed by Chris Fair. Described as “high-tech Etch-A-Sketch.”

“The Moth StorySLAM Chicago:Joy” at Mayne Stage, 1330 W. Morse Ave., 8:30 p.m. Stories about joy in all its forms.

“Nervous Breakdown” at The Annoyance Theatre, 851 W. Belmont, 9:30 p.m. Stand-up meets improv. Stand-up comedians use audience suggestions to create material on the spot. Hosted by Tyson Karrasch and Nick Rouley

Chicago Underground Comedy Presents “Best of Guest Fest Part 2” at Beat Kitchen, 2100 W. Belmont, 9:30 p.m. Birth place of groundbreaking comedy. Original comedy home of Beth Stelling, Cameron Esposito, Dan Telfer, TJ Miller, Kumail Nanjiani and many more. Come see the current extraordinary cast and the always stellar line-up.

“Lindsey’s Calling” at MCL, 3110 N. Sheffield, 10:00 p.m. “A group of three best friends who love to play hard and explore every given moment together. Extremely connected from the top, they ask you to come into their world. Laugh, Cry, Love. And let’s ride this thing until the wheels come off.” Featuring: Logan Hulick, Abby Vatterott, and Grant Micheal Johnson. (I’m not sure what this means, but it makes me want to find out.)

104th Mainstage Revue: “Fool Me Twice, Déjà Vu” at The Second City, 1616 N. Wells, 11:00 p.m. Directed by Jeff-award winning Director Ryan Bernier. Shows throughout the week. Tonight’s early show is sold out. Check out this great review by the Chicago Tribune’s Chris Jones. He calls this show “exceptionally funny.”



John Oliver at The Chicago Theater, 175 N. State, 7:00 p.m. and 10:00 p.m. The former Daily Show star and current host of HBO’s Last Week Tonight with John Oliver is here tonight and New Year’s Eve. In 2015 alone, John Oliver won Emmy, Peabody and Writers Guild Awards and also received the GLAAD Media Award for Outstanding Talk Show.

“The Riff” at Brisku’s Bistro and Bar, 4100 N. Kedzie, 7:30 p.m. “This is not your ordinary mic! You pull from a box to reveal a name/phrase/topic to do your 4 minute set.”

Michael Palascak at Zanies, 1548 N. Wells, 7:30 p.m. 

Jessimae Peluso at Zanies, 5437 Park Place, Rosemont, 7:30 and 9:30 p.m.  Jessimae Peluso is the star of MTV’s Girl Code.

Ron Funches at Zanies, Pheasant Run Resort, 4051 East Main St., St. Charles, 8:00 p.m.  Ron Funches is the star of NBC’s Undateable and a regular on Comedy Central’s Kroll Show. According to Wikipedia, he holds the record for most wins as a panelist on Comedy Central’s @midnight.


“Improvised Twilight Zone” at The Annoyance Theatre, 851 W. Belmont, 8:00 p.m. “All new, stylized moral parables every show.”

“Drunk Science” with Sean Flannery at The Comedy Bar, 500 M. LaSalle, 8:00 p.m. Sean Flannery’s drinks and high jinx stories are legendary. At “Drunk Science” you’ll find out what’s going on in the mind – literally – when that stuff is happening. The science of comedy combined with the comedy of science by a master comedian and storyteller.

“Soul Brother, Where Art Thou” at Second City, 1608 N. Wells, 8:00 and 11:00 p.m. This e.t.c. revue has show times throughout the week. Check web site for more.

“Supply and Demand” at The Laugh Factory, 3175 N. Broadway, 8:00 p.m. “We will mix the super famous with the next big thing for 90 minutes of crushingly funny comedy. You never know who is going to stop by and blow the doors off – expect the unexpected. And save some coin by buying your tickets early – as we sell out, the price goes up. Because this show is all about supply and demand.” Featuring Jeff Arcuri, Caitlin Checkeroski, Marty DeRosa, Calvin Evans and more TBA.

“Catholic Guilt Presents: Is That My Pew?” and “Top of the Sixth” at iO, 1501 N. Kingsbury, 8:30 p.m. Double feature. “Catholic Guilt” is Elizabeth Andrews and Mary Quinn answering life’s hardest questions: “ … will you and your lover remember how you met? Can a song change the sexuality of a room of people? Can one overcome the guilt placed on them from a strict Catholic upbringing to write a sketch show dealing with very uncatholic concepts? You’ll have to see the show to get the answers.”

“Top of the Sixth” is a one-act play about how a Cleveland Indians announcer reacts when a family crisis breaks out in the middle of a ball game.

“Comedians You Should Know” at Timothy O’Toole’s, 622 N. Fairbanks Ct., 9:00 p.m. Six you should know.

“Stupid F@#%ing Nerd: An Ode to Losers” at iO, 1501 N. Kingsbury, 10:30 p.m. A sketch show by the group Secrets & Pies dedicated to the bullied and the underdogs.

[LAST PERFORMANCE] “Corey Does Too! Have Friends” at The Second City, 1616 N. Wells, 10:30 p.m. “An improvised show by Corey Caldwell and whoever else decides to show up.” Ticket alert!  Last week’s show sold out!




New Year’s Eve Comedy Events are listed here!



Tickets on sale for “Wait … Wait! Don’t Tell Me” at, 10:00 a.m. Click here on New Year’s Day at 10:00 a.m. to snap up these hard-to-get-tickets.  This morning’s ticket sale is for the Feb. 11 Chicago taping.

“100 Proof’s Sixth Annual New Year’s Hangover Marathon” at ComedySportz Theater, 929 W. Belmont, 6:00 p.m. Four hours with twenty Chicago comedians of extreme talent. Also, one of Chad Briggs’ last Chicago appearances before he leaves us for L.A. Go see him! He’s excellent! Note: Chad will also be at the Lincoln Lodge showcase later tonight.

“Defiant Thomas Brothers” at Second City, 1616 N. Wells, 7:30 p.m.  Due to cheering crowds and rave reviews, DTB now have an open run at Second City. This sketch duo has original, comedic spins where others fear to tread and always with a stratospheric level of creativity and no fear.  In 2005, they had an 80-week run in Chicago and went on to take HBO’s Aspen Comedy Arts Festival by storm, returning home with the “best sketch group” award. What happened after that? No one knows. I just know that DTB were already a legend when they reunited this past September. It’s a Chicago comedy must-see.

This classic bit from DTB made them an international sensation when they performed it at The Edinburgh Festival Fringe in 2006. I think I’ve seen this clip one hundred times and it’s still not enough.

The Defiant Thomas Brothers kindly spoke with me here.

Adam Ferrera at The Improv, 5 Woodfield Rd., Woodfield Mall Store K120B, Schaumburg, 7:30 p.m.   Adam Ferrara has co-starred in the television shows Rescue Me and Nurse Jackie and with Kevin James in the movie Paul Blart: Mall Cop, among many other credits. He also has several Comedy Central specials and has performed for President Obama. NOTE: you can get tickets for dinner and the show or just for the show.

“Christmas Bingo: It’s a Ho Ho Holy Night” at Royal George Theater, 1641 N. Halsted, 8:00 p.m. The latest comedy from playwright Vicki Quade (Late Night Catechism). A night of interactive Bingo, trivia and religious wackiness in the best possible sense. Catholicism not required.  Open run. Fridays and Saturdays.

“Lincoln Lodge Showcase” at Subterranean, 2011 W. North Ave., 8:00 p.m. “The show’s mission is to showcase Chicago’s finest up-and-coming and touring comedians and past performers include Amy Schumer, Hannibal Burress, Fred Armisen, T.J. Miller, Marc Maron, Janeane Garofalo, Natasha Leggero and Kristen Schaal.” Tonight: Chad Briggs, Marty DeRosa, Ali Clayton.


“Drink, Date Laugh!” at The Laugh Factory, 3175 N. Broadway, 8:00 p.m. Comedians and audience members tell their funniest and most messed up relationship stories. Hosted by Paul Farahvar with Kristen Toomey, Andrew Sitter, Ali Clayton, Abi Sanchez, Marty DeRosa and more TBA.

“The Fancy Beer Comedy Hour” at Pint Chicago, 1547 N. Milwaukee Ave. 8:00 p.m. With David Drake, LiZ ZiNER, Geoffrey Thomas Asmus and Jason Melton. Hosted by Rudy Schultz. Free showcase. Donations suggested.

“Aphasia” at Second City, 1616 N. Wells, 9:00 p.m. “Remembering the things you forgot.”

“Funked Up Friday!” at The Laugh Factory, 3175 N. Broadway, 10:00 p.m.  Standard tonight is “as unpredictable and funky as possible.” Hosted by AJ Lubecker with Danny Kallas, Taneshia Rice and more TBA.

“Butthead’s Mahaliday Bash” at iO, 1501 N. Kingsbury, 10:30 p.m. A holiday extravaganza of sketch, improv and music.

“The Best of the Best of the Best of the Best” at iO, 1501 N. Kingsbury, 10:30 p.m. Thirty-six performers compete at various improv forms.

“Pimprov” at CIC Theater, 1422 W. Irving Park Rd., 10:30 p.m. This famous night of comedy features pimps improvising. Back at CIC for a limited run.

“BEEF” at The Laugh Factory, 3175 N. Broadway, 11:59 p.m. Chicago’s monthly insult show. Audience members can volunteer to be roasted or volunteer to sit as far away from the stage as possible. Hosted by Sean White and featuring more TBA. (Promo below mentions a different venue, but that’s because it’s from earlier this year before BEEF moved to The Laugh Factory.)



“Late Late Breakfast” at The Hideout, 1354 W. Wabansia, 2:00 p.m. Free pancakes at 2 p.m., show at 3 p.m. “Late Late Breakfast is the perfect comedy show for a drunken, weird Saturday afternoon. This Chicago-based show is a fast-paced, mixed-format open-mic created by comedians Tyler Jackson and Danny Maupin.”

“Paper Machete” at Green Mill Jazz Club, 4802 N. Broadway, 3:00 p.m. This fabulous weekly spoken-word showcase features comedians, actors and writers. Lots of famous names, but you don’t have to be famous to participate. If you would like to audition, be on the look-out for your opportunity at The Mash. Check site for line-up announced in the days before the show.

“Comedy Sportz” at Comedy Sportz Theatre, 929 W. Belmont, 6:00 p.m., 8:00 p.m., 10:00 p.m. Classic Chicago improv show. Two teams compete based on audience suggestions to create the best comedy scenes, songs and games. For all ages. Check schedule for many shows throughout the week.

Adam Ferrera at The Improv, 5 Woodfield Rd., Woodfield Mall Store K120B, Schaumburg, 7:00, 9:15 p.m. 

Michael Palascak at Zanies, 1548 N. Wells, 7:00 p.m., 9:00 p.m., 11:15 p.m. 


“The Two-Hour Comedy Hour” at Gallery Cabaret, 2020 N. Oakley, 7:00 p.m. “The Two-Hour Comedy Hour is kickin’ 2016 off with a bang with our extra special 42×42 show. This is the show where Two-Hour celebrates its weekly Tight 42 Seconds feature by booking 42 of Chicago’s best comedians to do 42-second sets, featuring full-length sets from four headliners. This time around, one of those headliners will be OUR NEW THIRD PRODUCER. Who will it be?? ONLY ONE WAY TO FIND OUT. Hosted by ANDY FLEMING & J. MICHAEL OSBORNE. Featuring showcase sets from: -NATALIE JOSE, JEFF ARCURI, CAMERON GILETTE and ???.”  Click here to see the all-star 42-comedian line up!

“Under the Gun Third Annual Improv Classic” at Under the Gun Theater, 956 W. Newport, 7:30 p.m. The five-week improv tournament kicks off.

Damon Williams at Riddles Comedy Club, 5055 W. 111th St., Alsip, 8:00 p.m. and 10:00 p.m. Damon Williams’ birthday show!

“Blackout Diaries” at High Hat Club, 1920 W. Irving Park Rd., 8:00 p.m. Hosted by Sean Flannery, this evening features comedians and regular folk telling their own legendary drinking stories. The audience will have a chance to ask questions. Featured on NPR, Comedy Central and in all the major Chicago papers as one of the city’s most recommended events. Saturdays. Get tickets soon – sells out fast!

Drew Frees at The Comedy Bar, 500 N. LaSalle, 7:30 p.m., 9:30 p.m. Drew Frees is a nationally touring comedian who got his start in Chicago.

‘Lil Rel’ Howery at Jokes and Notes, 4641 S. King Dr., 8:30 p.m., 10:30 p.m. This star of NBC’s The Carmichael Show grew up in Chicago. Hosted by M. Dubs and featuring Dave Helem.

“The Yeah Buddy Awesome Time Comedy Show” at Brainstorm Comics, 1579 N. Milwaukee, 8:30 p.m.  Free comedy showcase (donations accepted).

“Titus Gunn Comedy Show” at Underground Wonder Bar, 710 N. Clark, 9:00 p.m. A night of comedy hosted by Titus Gunn and featuring Sonia D., Mona Aburmishan, Bryan Christopher, I.K., Shawn Morgan and with music by Robert Allen and Joe Rodriguez.

“Dear James Franco” at Under the Gun Theater, 956 W. Newport, 9:00 p.m. Comedy springs from letters written to celebrities. Back by popular demand after a successful run last fall.



“Sunday Morning Stories” at Second City, 1608 N. Wells, 10:00 a.m.  For new and seasoned storytellers with opportunities for storytellers-to-be.  Click here to sign up. Hosts: Kevin D’Ambrosio, Justin Flowers, Lauren Huffman, David Slattery, Billy Sullivan and Ranjit Souri who is the creator and executive producer of the show. Technical Director: Zach Stinnett

“Sunday Morning Stories” is followed by …

“The Sunday Morning Open Mic” at  Second City, 1608 N. Wells, 11:00 a.m. Click here to sign up. Hosts: Adam Bowman, Kevin D’Ambrosio, Justin Flowers, James Knowles, Val Jencks and creator and executive producer, Sanjit Souri. Technical Director: Zach Stinnet.

“Bust-A-Gut Sundays” at Flavor Brunch, 17575 S. Kedzie, Hazelcrest, 7:00 p.m. Tony Sco, of 106.3 and Windy City Live, just announced that he’ll be hosting this comedy showcase every Sunday. One of  my favorite things is when Windy City Live starts and I see Tony Sco co-hosting.

“The Annoyance Film Night” at The Annoyance Theatre, 851 W. Belmont, 7:00 p.m. Monthly screenings of different indie films.

“Blipsters on Broadway” at The Laugh Factory, 3175 N. Broadway, 7:00 p.m. An alternative comedy show hosted by Dave Helem and The Nightly Show’s Felonious Munk.  Expect anything: music, commentary, comedians touring through who drop in to test stuff out. All possible. The show’s mantra is “If you think you’ve seen this, you haven’t.”


Adam Ferrara at The Improv, 5 Woodfield Rd., Woodfield Mall Store K120B, Schaumburg, 7:00 p.m. 

104th Mainstage Revue: “Fool Me Twice, Déjà Vu” at The Second City, 1616 N. Wells, 7:00 p.m. Directed by Jeff-award winning Director Ryan Bernier. Shows throughout the week.

“Arguments and Grievances” at Schubas, 3159 N. Southport, 8:00 p.m. Hosted by Kevin Brody. Featuring Kristen Toomey vs Derek Smith (Size of the boat vs Motion of the ocean), Tim McLaughlin vs Bobby Condon (Van Morrison vs Van Helsing), Lisa Peters vs Caitlin Chekeraski (Cats vs Dogs) and Reena Calm vs Joe Fernandez.

Comedy of Chicago Showcase at Henry’s, 18 W. Hubbard, 8:00 p.m. A showcase curated by UPDATE 12/30: show is canceled.

“Generals” at The Annoyance Theatre, 851 W. Belmont, 8:00 p.m. “Each week Antoine McKay (Empire) and Christy Bonstell will host a different top stage actor from theaters like the Steppenwolf and The Goodman, who will perform three of their favorite monologues. McKay and Bonstell will use this information to inspire a series of scenes, hopefully encouraging the actor to play along as well.”

Michael Palascak at Zanies, 1548 N. Wells, 8:30 p.m. 

“Pour Humor: Service Industry Night” at The Laugh Factory, 3175 N. Broadway, 9:00 p.m.  Featuring Alex Orozco and Kris Flanagan. “Back by popular demand, our “Service Industry Night” welcomes bartenders, servers, and bar and restaurant workers — along with their family, friends, and everyone else! Bring in your restaurant check-stub or event invitation for exclusive $10 tickets!”

Sup! with Polar Pig” at iO, 1501 N. Kingsbury, 10:30 p.m. Open mic jam plus a variety show plus improv. “SUP” stands for “Show Up and Play.”


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