Press Start: An Improvised Musical is a hilarious, high-energy full improvised musical inspired by the games you know and love. Each show, our cast creates a brand-new adventure on the spot using audience suggestions, complete with original songs, unforgettable characters, epic quests, and plenty of unexpected twists. From fantasy kingdoms and cozy villages to space battles and chaotic multiplayer mayhem, no two shows are ever the same. Whether you're a hardcore gamer or just love comedy and live theater, Press Start is a one-of-a-kind experience that turns the magic of games into a fully improvised musical adventure. Grab your party and get ready to press start.

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

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!

Mentalism meets improv comedy in the entirely unique form created by Annoyance founder Mick Napier. There is truly nothing else like it.

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

Sam Nelson and Blake Carlson are drifters. Vagabonds, even. The high of live performance potent enough for them to ride on, gig to gig. Now they're in stuck in the great city of Chicago, and if we all just laugh loud enough and smile wide enough, they'll be able to make it home safe and sound. All the way from Richmond, Virginia, Blake and Sam have lugged a rollie backpack full of their favorite jokes to share with the Annoyance Theater. Enlisting the improv stylings of Hail Marys and hosted by David Factor, this show promises to not only tickle but also delight.

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!

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

Circuit Comedy Club presents Tales From The Windy City. An hour-long comedy show featuring local Chicagoans telling their truest tales to inspire our cast to create a hilarious series of improvised scenes. Closing out the night, jump onstage and jam out with the cast! FREE for students

After suffering a lung collapse in April, comedian Luke Herman revels in what’s left of his life with amazing and unholy guests. This variety show features improv from Hail Marys Comedy (with guests Ally Montgomery and Melina Arevalo) and standup from Luke Herman, Isabella Sinisterra, Hannah Beck, and Sam Rocha.

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.

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

Deep in the heart of a volcano, Crash Test Labs is hard at work creating the funniest sketch ever. Join Gus, David, Jonah, and their robot sidekick for an hour of outrageous laughs and non-stop fun. Featuring original songs, characters, and the best alternative stand-up comics in Chicago.

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!

Hundreds of miles offshore, a luxury cruise liner cuts through the Atlantic at double speed. At the helm? A megalomaniac captain in love with his own reflection & exploiting his beleaguered crew past their breaking point. As rebellion brews below, things are also heating up above deck! Love blossoms among thrill-seeking women, a heavy metal band grapples with their past & present, and a council of walruses issues a prophecy for destruction. Rudder Bullshit is a new play from the masterminds that brought you Docked and Loaded. Featuring original rock ballads that are guaranteed to make you put your lighters up! Hop aboard and strap in for what critics are calling "an edge in your seat adventure"! It's some Rudder Bullshit!

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.

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.

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.

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!

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’re (un)invited! Uninvited is a fully improvised event-based disaster in three acts. The audience supplies the suggestion of why we’re gathered, and then we show you what wackiness and whimsy unfolded before, after, and then during the event. Join us for a one-hour chaotic descent into why we got ourselves Uninvited.

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.

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 Miss Annoyance Pageant celebrates women from all walks of life. Our pageant is founded on the commitment to uphold standards of fairness and integrity. Communities thrive once an appearance-based ranking system is introduced. The Annoyance Theatre needs to crown the most beautiful, most intelligent, and most gorgeous girl. This beauty pageant is recognized by the United States National Pageantry Association as “a sham” with a “net-negative effect on society” that “poses certain national security concerns.” If you value beauty, knowledge, and subjective judgement- you will find it here at the 2026 Miss Annoyance Pageant.

Katie Rae Horn and Laura Dellis are recent winners of the Chicago Reader’s Best Comedian (Non-Standup). Together, they are putting together a variety show showcasing their award winning comedy and special guests.

Screw the algorithm! Sketched Out is a digital sketch comedy showcase rebelling against short attention spans. Too weird for your average feed, this is the gold that never makes it past the social media gatekeepers. Join us for a night filled with digital sketches on the BIG screen and meet some of Chicago’s boldest sketch artists, from up-and-coming voices to seasoned comedy pros. Have a sketch you want to submit? Check out @SketchedOut_Digital for submissions

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.

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

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.

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.

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

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

Blending smart ensemble improv with the energy of late-night television, this one-of-a-kind show plays out like a live talk show episode. Improvised scenes introduce unforgettable characters, then those characters take a seat on the interview couch, where a genuinely curious host explores the relationships, motivations, and absurd truths that make them tick, revealing even more than the scenes themselves.

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.

Famous, Eventually follows a young Southern woman who declares that she will do anything to become a star, anything. She makes a deadly bargain with a visiting entity for the life she believes she deserves. The show is loosely autobiographical, but it pushes Anna’s real pursuit of a creative life into a heightened, cartoonishly absurd, and much darker world. How much of yourself are you willing to sacrifice to become someone?

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.

July 2nd, 1937. Many believe that Amelia Earhart met a watery demise, when in reality…she time travelled to the year 2026, landing at the Annoyance Theatre! But what’s worse than almost drowning in the Pacific Ocean? Drowning in OBSCURITY! Find out if Amelia Earhart manages to land the ultimate comeback in this campy 75-minute two-act dramedy.

What if the heroes never saved the day? What if one town WAS swallowed up by a hellmouth, or infiltrated by alien imposters? Cryptic is a fully-improvised documentary in the style of true crime stories, exploring the aftermath of a small-town mystery and how it brings a community together. Complete with interviews, theories, accusations, and revelations, you'll be shocked by what we uncover. If you love true crime and tall tales, you'll love Cryptic!