AJ is that classic gay guy mix of ironic distance and earnest enthusiasm, and he's determined to make this the year he gets a boyfriend. Just like going to the Olympics, finding love is all about setting goals, pounding the pavement, wanting it the most. Through swiping, ghosting, and mismatched expectations, AJ's disappointment cracks his facade and reveals why he's so urgent, and hopeful. Single Sided is a hilarious, and at times heartfelt, show that explores the all too retable intersections of desire, technology, and healing.

Looking for a Stand-up Comedy Open Mic that’s a supportive room and always a good time? Look no further than the Ya'll Mic. Whether you’re a seasoned comic, an improvisor who’s always wanted to try standup, or you just decided that today’s the day for your first open mic (kudos) – The Ya'll Mic is a great venue to workshop your bits. The show is every Tuesday from 5:30pm – 7:30pm. Signup is online and the signup sheet is posted on Facebook & IG on Mondays. The list is emailed out a few hours before the show. Comics get 4 minutes of stage time (and a lifetime of memories.) While all are welcome, the room prioritizes BIPOC, LGBTQ+, and Femme comics. Come laugh with us!

Open Stage is an opportunity for anyone to get on stage and try out whatever they're currently working on - standup, sketch, songs - you name it. At Open Stage anything can happen and it usually does!

You've been summoned...to laugh. Jury Duty is a fully improvised courtroom comedy where the only thing on trial is sanity itself. Each night, the cast creates a brand new legal disaster based on audience suggestion, questionable logic, and total chaos. Watch as the foreperson loses their mind, evidence makes things worse, and deliberations go off the rails. No script, no rules, no justice. Just comedy The trial is fake, the laughs are real

Is there any greater joy than dancing your face off with your best friends? Absolutely not. Join Caroline, Tom, and Maryrose this summer to do exactly that. They’re back for their fourth sketch show at The Annoyance. Don’t miss it, come party with Cafe Lounge Underwater!

Missed Call is a premiere Chicago comedy group that writes and performs an entirely new sketch show every Friday.

Glow out with us at The ShowOut - an ensemble showcase of some of the Chicago comedy scene's best Black comedians! Featuring: Joseph Jenkins, Kiki Hughes, Lazarus Howell, Skylar Harts, Hezekiah Duncan and Maya Haughton

Kath Courtney and Rockie Wenrich are: Father Figures! Two dudes with the ability to fix your car, be fuckable, and die before you really get the chance to understand them. Special thanks, as always, to Chelsea Matkins. Made for fathers and DILF-enjoyers everywhere.

Kit culture, FIFA (corrupt?), gooooaaaaaaaaaaallllllllllls, and the MF WORLD CUP - this is the only Soccer show you'll need for the summer. This will be a soccer-centric variety show for the ages featuring sketch, improv, and a lot more lead by Ian Mullen supported by a team of soccer stars including Max Kantor, Annie Scott, and Mitch Winkler. And finally, a special Chicago soccer guest every week!

Every Wednesday, this group of Annoyance Program graduates performs The Insignificant Mile, a creative twist on a classic form in which players create a strip mall through audience suggestion. Each show features four unique locations, and a brand new cast of characters that exist in the world they created. With new guest openers every week, the Insignificant Mile is sure to leave a significant impact on audiences!

New forms. New Players. Big Laughs. Every week is a new and different show. So what you see, no one else will see.

Enjoy an evening of off-the-cuff improv with some of the best emerging talent in the Chicago area. Fire & Beer is a fully improvised comedy show that explores the dark sides of life, relationships and human beings. The show features the Annoyance House Ensemble who excel at both long- and short-form improv. You can expect lots of laughs during this unpredictable improv show.

Come join us as we explore different historic moments and blend together factual storytelling with creative and witty moments that were never documented. Each show will cover a different event that is researched and studied. We, then, take that information and improvise everything else that was lost to history.

It's a solo character showcase featuring the students of our latest class! Educating students on preparations for showcase performances, don't miss the next generation of character-based talent!

To What End? returns with three ALL NEW comedy variety hours at The Annoyance! Join us for a night of laughs, gags, & bits from some of Chicago’s finest comedians. New line-up every show!

Fun in Moderation is a New York City–based sketch comedy team featuring Kendall Bowden, Austin Elias-de Jesus, Syd King, and Nick Ryan. With backgrounds in UCB, stand-up, and character performance, their work focuses on character-first, game-driven sketches. The group has performed at NY Comedy Festival, SF Sketchfest, Caveat NYC, Asylum NYC, Austin Sketchfest, Philly Sketchfest, and was recently featured in The New Yorker (a surprise to them, too). Past openers include: Adam Conover, Vannessa Jackson, Dan Toomey, Moss Perricone, Maddie Wiener, and many more!

Sharp. Polished. Unmissable. Gold Standard Comedy lives up to its name with a lineup of some of the finest comedians at Windy City Comedy Fest 2026. Every performer is a proven crowd favorite—delivering stand-up that’s clever, confident, and consistently funny. This late-night showcase brings together top-tier talent for a smooth, high-quality comedy experience that highlights the best of the fest.

See how short form improv works and even try it out yourself! This short form jam is open to Annoyance students and other improv performers. Join us!

The Annoyance's very own musical ensembles. Every Tuesday at 8pm, two groups improvise brand new musicals based on audience suggestions. Featuring Musical Director Lisa McQueen and starring the Annoyance Musical Ensembles. Follow us on instagram: @tuesdaymusicalimprov

Welcome to JUICY, Chicago’s premier gossip-based comedy show. Each month, a cast of HOT improvisers spill their own real stories, anonymous audience confessions, and perform fast, filthy improv. Known for a cast with undeniable onstage chemistry, this show is the ultimate Wednesday night out! What happens at JUICY stays at JUICY… but you’ll be dying to tell everyone you were there.

The world is crazy, but thankfully so are we! Join KEEPIN' TABS NEWS, a monthly news parody and political satire sketch show, as we break down today's headlines and resist the urge to break down, emotionally. Join us at the Annoyance Theatre on 1/22, 2/19, and 3/19 for your monthly dose of hard-hitting journalism mixed with side-splitting humor. There's too much happening in the world for you to keep track of it all, that's why we're here for you, keepin' an eye on the powers that be, keepin' you laughing through the turmoil, and KEEPIN' TABS! Featuring: Andie Nash, Ashley Bland, Baylor Barnes, Courtney Zelzany, Drake St. Pierre, Jessica Kung, John Doan, Mary Fiala, Mike Mazzella, Salman Lee, Sophia Fattore, Tiffany Chappell, and Xzavier Dean. Directed by: Johanna Medrano

Come see Billionaire Billy Bangles and his crew of well-meaning stargazers attempt wild schemes to bring profitability to their piece of junk space cruiser. Sketch comedy, digital shorts, song and dance — free space cruise included.

WOAH! NEW EVERY MONTH. A raucous. raunchy, sometimes juvenile but always funny sketch show that will make your daddy give your mommy a pearl necklace... to clutch. Get tickets now, they're selling faster than a Stewie doll at Spencer's. DM: @Antivirginclub proof you bought tickets and we will draw you boobs.

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 in a week with no rehearsals. Featuring a powerful collective representing a wide cross-section of the Chicago comedy community, the material varies every week.

Al's a new gay in Chicago looking for love in the big city when he bumps into the most beautiful man he's ever seen on the streets of Northalsted one night. Desperate to make his acquaintance, Al follows him into the legendary bathhouse Steamworks. As he makes his way through the maze of jacuzzis, slings, gloryholes, and fuck benches, Al makes a wild group of friends who help him discover what love might really mean when everyone's covered in cum.

They take edibles. Then they improvise. There's a 'too-high' button, for when it gets too crazy.

In an attempt to save the rec center from being torn down by an evil corporation backed by private equity, a beloved group of characters do what any 80s trope does best: put on the best variety show they possibly can. Showcasing Chicago's best comedic talent across all forms of sketch, improv, stand up, and music.

Step into the one glamorous but now lovingly frayed Blue Velvet Lounge, where the only thing not improvised are the jazz standards crooned by lounge singer Seth Lowery. As Seth’s velvet voice fades, the ensemble sweeps in, spinning spontaneous scenes inspired directly by the songs just performed. One moment, you’re eavesdropping on the eccentric regulars tucked into the lounge’s candlelit corners; the next, you’re whisked far beyond the club to follow the unexpected lives of the characters you just met—bartenders with secret ambitions, mysterious strangers with tangled pasts, and dreamers who stepped into the Blue Velvet for reasons they can’t quite explain. Playful, surprising, and steeped in a retro-cool vibe, this show blends live music and improvised storytelling into a one-of-a-kind night where every note inspires a new twist—and every visit to the Blue Velvet reveals something you’ve never seen before.

BIKINI BTTM?? well honey where are the tops? The 5th Annual 18+ Annoyance Pride party is back on 6/28 with drag programming all day including headlinders Jasmine Masters and Hoso Terra Toma! Your ticket gets your into every show all day including: Strapped hosted by Irregular Girl and Siichele with performances by True Romance and Alonza Sol Sade and headliner Hoso Terra Toma (2x Dragula Finalist) The 5th Annual 21& Under Pageant-- our yearly competition for 18-21 year old drag performers to compete for the title! Hosted by Squeaky and Starr Banks with special guest judges Chicago drag icon Stephanie, internet celeb Tannertan36 and last years winner Grace Van Duran. Gag! featuring headliner Jasmine Masters from Rupauls Drag Race! Hosted by Neutral Gena, Ari Gato, Rachel Slurrz, and Derry Queen with performances from Pagina and Armani Von Paris. The 2nd Annual Lip Sync Assassin Tournament... Chicago's best performers compete for the title and cash prize where the judges and audience vote for their favorite! Competitors this year includes Kara Mel D'Ville, Kenya J Sanchez, Smokey Karamikeal, Masha Potato, Lezbian Minnelli, Seana, Yuiza Beach and Ash Wednesday! Special guest judges The Front Row Divas, Kitty Banks, and Laila McQueen from Rupauls Drag Race!

In this show you will hear testimony from a parade of character-witnesses on the stand, argue over audience submitted petty-offenses like: that one friend who sends to many partiful reminders, or sneaky links who sneak IG pics while your sleeping, or rude people who chat on speaker riding the CTA. Our jury (aka you) hold the power to decide what constitutes a violation of unwritten but entirely serious social law & order! Fake lawyers and real comedians litigate to the death in the trial of the century & try not to get Overruled!

I'm about to party on you... Party 4 U (For Me) is a solo show/party/extravaganza to celebrate ourselves amidst this year of 2026 which many are saying is chalk-full of all-consuming global and personal chaos. We're talking music, we're talking characters, we're talking improv, we're talking stories and? We're talking more than that. So? Raise your glass if you are wrong in all the right ways. "Watch me watch me watch me party on you (yeah) Party on you, party on you, party on (x12)" - Charli XCX

Magician Jay Collen performs selected tricks covering a century of close-up magic created by Chicago magicians. Audiences are limited to 30 per performance so that everyone can experience the magic up close. Audience members are encouraged to participate in discussion about the each trick and its Chicago history. Jay performs performs extensively, is the Senior Magic Teacher at Magic, Incorporated, has written acclaimed books on magic, and is a magician member of the famous Magic Castle in Hollywood.

Actress and comedian Gavin Connell takes you through her coming of age, reflecting on her trans-ness through every embarrassing story. From school crushes to college secrets to theatrical misadventures, take a walk down memory lane with this fresh, shocking, interactive, at-times musical standup show!

Annoyance students let loose in this student improv jam - all Annoyance students are welcome! A great opportunity to meet other members of our improv community.

Are you and your improv team looking for another place to get on stage? We've got a warm and supportive room ready to give you laughs and claps! Bring your own team to Annoyance on Tuesday nights to get a rep in and giggle. If you don't have a team to bring, no worries! There's a mashup team and we're happy to throw you on it! Signups are at 8:30PM and we'll hit the stage at 9:00PM. See you every Tuesday!

We're a group of not-so-young women comedians who aren't afraid to show tits but ARE afraid to show ass. We make shit chaotic and smart, and that could never be written by a man.

Hey all you sexy summer somebodies! DNA is back with the hottest show of the year (we've asked the theater to set the thermostat to 105 degrees). Enjoy an hour of non-stop sketches, zingers, and even some audience participation? My Wet Hot DNA Summer Graces the Annoyance's main stage June 18th and 24th at 8pm!

Blue Dress is a gay mashup play that reimagines Alice from Wonderland and Dorothy from Oz as lesbians. After stumbling through a looking glass, the two team up to find their way home. But as they encounter familiar characters and shifting realities, they discover that belonging means knowing who they are and dismantling the roles they've been assigned. Blending camp, comedy, and emotional honesty, Blue Dress explores identity, queer friendship, and the courage it takes to tell your own story.

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together an intricate Hitchcock-like drama, while holding true to the amount of drinking shown in his movies. You'll barely be able to stand the suspense, and the cast will barely be able to stand.

Annoyance founder Mick Napier created the Trigger Happy form out of a desire to make improv look as slick and beautifully put together as a scripted show. Through a language invisible to the audience, the fully improvised show magically comes to life. There is truly nothing else like it. An Annoyance Signature Improv show. Review: https://www.newcitystage.com/2015/01/31/review-trigger-happythe-annoyance-theatre/

An hour long comedy show featuring some of Annoyance Theatre’s best and funniest. Show Runner: Hails Reeves

The Hail Marys are back and they are bringing Church to The Annoyance. Join Ellie, Mary, Declan, Isabella, and Maryrose for an 8 o'clock mass like you've never seen before. There will be openers, featured saints, and of course improv. Come and repent sinners!

Inspired by the classic movie and hit FX show "Fargo", Duluth takes audiences into the world of true crime in the Midwest. The cast will improvise a story of murder, malfeasance, and general mayhem, all set against the backdrop of an audience member's hometown. Complete with cops, criminals, and the everyday townsfolk who get caught in between, this show contrasts horrible crime with "Minnesota nice".

An LGBTQIA+ themed variety show featuring some of Chicago's strongest and most diversely hilarious voices!

Throw out your boredom and come see Stardom Awaits! Our cast of contestants compete to be the Biggest Star of them all! Each round of short form games is an opportunity for them to Win! Stardom Awaits is sure to be the highlight of your week. Brimming with enthusiasm and entertainment!

Hail and well met, traveler! Grab a drink, put up your cloak, and I’ll tell you a tale. Escapades is a completely improvised choose-your-own adventure. Sprinkled throughout each story are opportunities for the audience to vote on what happens next. Whether we’re riding jetpacks on Mars or a unicorn through a gumdrop forest, you’re guaranteed a night of gasps, laughs, twists, turns, and daring rescues. Excelsior!

Andrew Sulfsted and Wyatt Menci felt the higher calling to be an Alderboy, a position in local politics that resides at the very bottom of influence. In order to build their way to the top, the two recruit talent from their ward to boost political sway and community swagger. Can the Alderboys save Lakeview East? Only if their constituents have the gumption they require. Or it may just save itself. Either way, the Alderboys are here to stay.

Tiny Idea Live! is a sketch comedy show by Ann Nelson, Eva Nemiroff, and Hrannar Björnsson, featuring all-new live sketches and never-before-seen videos! Tiny Idea’s videos have gotten more than 100 million views and have been featured in Vulture. They currently write for Dropout’s Game Changer and Make Some Noise. The trio has a combined age of 80 and has been described by a TikTok comment as “three of the most average-looking people I’ve ever seen.”

This is one of four official Industry Showcases at Windy City Comedy Fest 2026—where selected performers take the stage in front of bookers and industry professionals from across the Midwest. Designed to spotlight top talent from the festival, this showcase brings together comedians ready to be seen, booked, and remembered. By bringing industry to Chicago, Windy City Comedy Fest is helping shape the future of the Midwest comedy scene—connecting performers with real opportunities on a regional stage. Hosted at the Annoyance, this is a high-stakes, high-quality show.