Comedy Shows

Come to enjoy great comedy improv, sketch shows, plays and musicals. Age restriction is 14+ for our shows; please know our material is uncensored and may have content that’s more for mature audiences. If you’re not sure if something’s right for your party, just give us a call!

The Customer is Always Right? Holiday Edition

The Customer is Always Right? Holiday Edition is a hilarious improv show that let’s the audience take a peek into the service industry and all of the pain that comes with it. Watch as performers recant tales of horror from … Continue reading Comedy Shows

Shark Tank: The Musical
(a parody)

Ever watch the tv show Shark Tank and think “That show would make a great musical!”? Well, your friends at The Annoyance did. A great cast of Annoyance regulars play your favorite sharks Mark, Daymond, Kevin, Lori, Barbara and Robert along with all kinds … Continue reading Comedy Shows


SHEBEAST is the loudest, nastiest, sexiest group of he-women you’ve ever seen. They stomp through life making jokes and taking names. You a down right DIRTY DOG? Then this show is for you. The ladies get in your face, and … Continue reading Comedy Shows


From the  “Best Improv Troupe in Chicago: 2016” – Chicago Reader It starts with an audience suggestion then the players create a full length thriller in the style of Alfred Hitchcock. There could be murder, car chases, gun play, beautiful … Continue reading Comedy Shows

Baby Wine

Baby Wine is an all-gay improv supernova with universally relatable scene-work from a cast filled with unique points of view. Baby Wine can only be described as a fast-paced mix of complex relationships with manipulated gender roles and pop culture … Continue reading Comedy Shows


Come and watch Trash do some amazing improv!

The Holy Fuck Comedy Hour

See a collage of character studies, scenes, songs and maybe even some audience interaction, all written in a week by some of Chicago’s most accomplished comedians. The “Holy Fuck Comedy Hour” is a curated hour of eclectic, comedic material written … Continue reading Comedy Shows

The Annoyance Christmas Pageant (Evenings)

The Annoyance Theatre presents its annual Christmas Pageant, featuring a retelling of two classic holiday stories: A Charlie Brown Christmas and Rudolph the Red-Nosed Reindeer. The all-new cast gives these classic holiday television specials a hilarious spin, all the while … Continue reading Comedy Shows

Marry. Fuck. Kill.

What if life played like a game? Marry. Fuck. Kill. Everyone does at least one of these in their lives. At this show, we do all three. Improvised magic right before your eyes. Marry. Fuck. Kill. Life is crazy and … Continue reading Comedy Shows

Fire and Beer (Annoyance House Ensemble)

NO SHOWS 10/7 & 10/14! The Annoyance House Ensemble improvises based on an audience suggestion. Feeling hungry? Add Dinner at Drew’s! Add dinner on to your show ticket for $29. Head over to Drew’s on Halsted, just down Belmont, for … Continue reading Comedy Shows

Bite Size Broadway

PREVIEWS 11/4 AND 11/11 You’ve never heard of Andrew Lloyd Webber’s relative, Bobby Lloyd Webber, but after this hysterical performance at The Annoyance Theatre in Chicago you’ll definitely be a fan. Webber wrote ten musicals while doing hard time in … Continue reading Comedy Shows

A Lill Annoyance Stand-Up Show

NO SHOW 10/7 & 10/14! A 1 hr li’l Stand-Up Comedy Showcase hosted by Lill Allison at The Annoyance in the li’l theater!!! FOLLOWED BY…A LI’LL OPEN MIC: OPEN MIC WILL BE BOOKED BY LOTTERY DRAWING THIS WEEK – You … Continue reading Comedy Shows

Annoyance Open Mic

NO OPEN MIC 10/7 & 10/14! The Annoyance’s only Open Mic Night! Come and try your hand at some standup or solo performance or simply just come to watch! Hosted by Lilly Allison. OPEN MIC WILL BE BOOKED BY LOTTERY … Continue reading Comedy Shows

Burlesque is More: Naughty and Nice

The “Rumble Room” is ready to battle the winter chills. Join our hilarious and talented dancers as they heat things up this holiday season. This show features some of the richest characters a comedic strip club could have this time … Continue reading Comedy Shows


This classic Annoyance show returns for the first time to the new Annoyance with a twist. As the male and female performers improvise, some will disrobe down to their skivvies, and others may offer just a quick peak. As sexy … Continue reading Comedy Shows


James and Jon were living it up as cruise ship comedians, until their ship accidentally sailed through the Bermuda Triangle. They mysteriously blacked out, and when they came to, they had a book of sketches bound in human skin. Now … Continue reading Comedy Shows

Laughter Than a Speeding Bullet

Come join Velvet Stallion, Chicago’s most dangerous Improv Team, in a super heroic extravaganza! You’ll laugh, you’ll cry, you’ll die a little bit inside as you watch super heroism like you’ve never seen it before!

Matt Damon Improv

The cast of Matt Damon Improv is comprised of all women of color “slaying improv comedy,” sometimes featuring a special guest white male(Matt Damon) or female (Lena Dunham) improv comedy veteran who can only speak when repeating things that the … Continue reading Comedy Shows

Take It Back

Take It Back! is a variety show where we reclaim acts that have been historically typecast and present them in a new light, featuring a more diverse cast and a more modern context. Think Oklahoma! meets Hamilton, with a Cabaret … Continue reading Comedy Shows

Let’s Go Bobby!

Let’s Go Bobby, is the story of a 12 year old boy, played by Jenelle Cheyne, who is trying desperately to fulfill his life-long dream of being on the school wrestling team. With the help of his family, friends, coaches, … Continue reading Comedy Shows

Student Jam

A night for Annoyance students to JAM!

Anarchy (an improvised rock opera) Presents: BURN IT DOWN

Anarchy is a completely sung, completely improvised rock opera featuring some of Chicago’s finest musical improvisers. With roots in modern musicals like Tommy by The Who, Green Day’s American Idiot, Rent, and Spring Awakening Anarchy stages an hour long show … Continue reading Comedy Shows

Sacrilege: A Nativity Story

Everyone knows the story of the birth of Jesus Christ, but haven’t we left out one very important point of view? Sacrilege follows Mary as she journeys to Bethlehem during her three day pregnancy, accompanied by her atheist fiancé and … Continue reading Comedy Shows

Chuckle F*ckers

Improv, sketch, music, stand-up, and everything in between. Come be entertained by Annoyance groups that perform new, original and experimental material! New acts every four weeks.

Super Human

These Humans are SUPER FUNNY! Come watch this group of seasoned pros take the stage for a night of extreme comedy.

Huggable Riot Variety Show

Huggable Riot slays Sketch Comedy! Come and watch as they perform a hilarious variety show with music, improv, sketch and a possible sneak peak from their upcoming revue “A Miracle on 45’s Tweet.”

Character Assassination

Character Assassination is a group of highly trained laugh-sassins, who always get the job done with very little mess. Come see an hour’s worth of big, memorable characters. Witness a sketch comedy that’s guaranteed to kill, or your money back

Messing with a Friend

Messing With a Friend features Susan Messing, and other invited talented and funny improvisors from around Chicago, from iO to Second City to The Annoyance. A collection of self-edited improvised scenes based on a single suggestion. A joyful, uncensored, and … Continue reading Comedy Shows

It’s Christmas, Goddamnit!

This year’s annual Christmas celebration at the James’ home has a macabre twist. Along with the traditional passive-aggressive silences and sniping, Dad has surprising news: he’s been dilly-dallying with the next door neighbor. Now, throw in the accidental murder of … Continue reading Comedy Shows

Shade Uncut Presents: Ant Farm

From a suggestion of a single location, the cast manifests a complex web of characters and relationships in real time. With sudden bursts of energy, these characters are examined and cross-examined to explore their most intimate thoughts and moments across … Continue reading Comedy Shows

Huggable Riot Presents: Miracle on 45th’s Tweet

Miracle on 45th’s Tweet is a sentimental, comedic reminder of when Christmas was a time of music, gifts, and free from worry. Whether through a sibling revealing our favorite winter sport to be problematic, an elf’s inability to break her … Continue reading Comedy Shows

Nuggets (Short Form Improv)

NOW EXTENDED ON THE MAINSTAGE!! NO SHOW 11/22 Nuggets is a short form improv show – think Whose Line is it Anyway but updated with a young, diverse cast! Each show features a six-piece of our performers navigating games, songs, … Continue reading Comedy Shows

Annoyance Presents Improv: Trigger Happy

The show consists of a series of unrelated scenes that are inspired by a single suggestion from the audience. During the show the cast share an invisible language that will trigger certain events, as if by magic. Feeling hungry? Add … Continue reading Comedy Shows

Matt Damon Improv Presents: We Out Here (the sequel)

Matt Damon Improv invites you to “We Out Here” (the sequel) – a special Friendsgiving showcase featuring some of Chicago’s hottest POC talent.  Improvisers are also invited to “Bring Your Own Team” and a canned good/non-perishable food donation for a … Continue reading Comedy Shows


Fishbowl hosted by Sight Unseen features a rotating selection of independent groups to open the show. Then, Annoyance Students will get a chance to enter their ID’s into a fishbowl. 5 students selected will perform in an improv jam with … Continue reading Comedy Shows

The Annoyance Christmas Pageant (Matinee)

The Annoyance Theatre presents its annual Christmas Pageant, featuring a retelling of two classic holiday stories: A Charlie Brown Christmas and Rudolph the Red-Nosed Reindeer. The all-new cast gives these classic holiday television specials a hilarious spin, all the while … Continue reading Comedy Shows

Nameless Numberhead

“NAMELESS NUMBERHEAD” is a sketch comedy duo with Chicago backgrounds but is based out of Charleston, SC (you know, that natural progression of Chicago to South Carolina). Their show is a post-apocalyptic vaudeville fever dream where the performers run all … Continue reading Comedy Shows

Steamworks: The Musical – NYE Show

STEAMWORKS: THE MUSICAL IS BACK FOR ONE NIGHT ONLY! The popular Annoyance Theatre comedy Steamworks: The Musical is coming back to finish off 2017! This singing and dancing extravaganza tells the hilarious story of a wide-eyed young man who moves … Continue reading Comedy Shows