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shows at Annoyance ...

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Tuesday Musical Improv

Tuesday

5/12

8:00 PM

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

Jury Duty

Wednesday

5/13

9:30 PM

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

Odd Jobs

Thursday

5/14

8:00 PM

Day jobs are just for material, right? Odd Jobs uses these comedians’ offices, co-workers, and customers as inspiration for all new characters. Come see Odd Jobs for a variety of characters and funny stories from some of Annoyance’s best performers.

Anti-Virgin Club

Friday

5/15

9:30 PM

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.

God Lens Book Release Show & Party

Saturday

5/16

3:00 PM

What a Saturday! It’s a book release of Mick Napier’s Satirical book about Biblical Morality! AND a mysterious and spurious demonstration of Psychic abilities by the acclaimed Napier and Estlin! AND a real live Biblical morality play that is 6 minutes long! WITH A book signing AND light banter AND social interactions WITH cocktails! ALL on a quiet Saturday afternoon! We like to say, “Duh-duh be there!! See ya!

Phat Dragon

Saturday

5/16

8:00 PM

Phat Dragon is a uniquely hilarious longform improv group originally founded in a college dorm room. Roommates Ian Toppall, Ben Levy, Josh Hoover, and Hunter Gill, would pack as many as 50 audience members every Wednesday night into a space that fire code said could only fit 12. After outgrowing their apartment, they now do weekly shows all over the city of Chicago. Phat Dragon combines a unique blend of charm, energy, and hospitality to make an hour of comedy you'll never forget!

We Took Edibles an Hour Ago

Saturday

5/16

11:59 PM

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

Collective Rage: A Play in 5 Betties

Monday

5/18

7:00 PM

Meet five different women named Betty: one rich, one lonely, one charismatic, one lovelorn, and one who keeps working on her truck. Oh, and one has decided to stage a production of that play-within-a-play by… that old English guy, what's his name? Ah, forget it. In Jen Silverman’s unpredictable comedy Collective Rage: A Play in 5 Betties, five women collide at the intersection of rage, love, and the “thea-tah,” provoking each other to take a look in the mirror and face the person they didn’t know they could be.

Keepin' Tabs

Thursday

5/21

8:00 PM

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

Fire & Beer

Saturday

5/23

8:00 PM

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.

Paint & Pyro

Wednesday

5/27

7:30 PM

“Paint & Pyro” is a fast-paced, 60 minute stand-up comedy showdown where five comics each perform a tight individual 5–6 minute set while the remaining comics paint live onstage, racing the clock and each other. When the brushes stop, the audience votes the best finished portrait and chooses the worst one to be dramatically burned in the alley, blending comedy, chaos, and creative destruction into one unforgettable spectacle.

Baby Wine

Friday

5/29

9:30 PM

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

HELP ME!!!!

Wednesday

6/3

7:30 PM

THANK GOODNESS YOU’RE HERE! A DEAD MIME NEEDS HELP. In this interactive mime seance, the audience must help a family of ghosts complete their unfinished business. Play charades, solve puzzles and pierce the veil between life and death on a madcap quest for forbidden knowledge.

Blue Dress

Friday

6/5

7:30 PM

Blue Dress is a fast-paced queer meta-fantasy that unites Alice from Wonderland and Dorothy from Oz in a shared, unstable world where familiar rules no longer apply. As they search for a way home, the two encounter strange characters, shifting realities, and growing tensions that challenge how they see themselves and each other. What begins as an adventure becomes something deeper as both are forced to question the roles they’ve been assigned and whether they’re willing to break from them. Blending camp, comedy, and emotional honesty, Blue Dress explores identity, friendship, and the courage it takes to define your own story.

Fool’s Gold

Friday

6/12

9:30 PM

Fool’s Gold is a hybrid comedy show with the structure of a stand-up showcase. The first half features 3-5 minutes from the host, a 5 minute guest spot of a solo-sketch/character comedian (if one is available—if not, this time is given to the feature), a 10 minute feature act and then a 30 minute headliner. Immediately following the headliner is a 10-slot open-mic. Sign-ups follow the same format as Open Stage sign-ups (starting 15+ mins before curtains) except the list is posted on the host’s socials and displayed in-person outside of the room right after the host introduces the first booked performer. Each open-micer (stand-up, clown, character, etc.) can perform 3 minutes maximum: the only requirement is it must be a solo comedy act with no tech requirements. Open-micers will be played off at 3 minutes, their voice being drowned-out by music for toddlers.

JUICY

Wednesday

6/17

8:00 PM

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.

Jamie Kilstein Can't Tie Knots

Tuesday

5/12

9:00 PM

Jamie Kilstein is an actor, comedian, podcaster, jiu-jitsu black belt, and the creator of Blue Belts, his first scripted television project which was nominated for the Grand Jury Prize nominated for RIIFF. His feature script “Sad Like Us” was a finalist for the Sundance Labs in 2025. Known for his standup on Conan, Showtime, and the BBC, Jamie began his career performing in coffee houses before making his mark at major festivals worldwide. In his early career he was mentored by Robin Williams, who said of him, “Jamie is amazing- he has a spark that energizes my conscience.”

Open Mic Night at a Bowling Alley

Wednesday

5/13

9:30 PM

In an attempt to up their Wednesday night sales, Dayton, Ohio's 3rd most popular bowling alley has decided to run its first ever Open Mic Night. Overrun with sign ups, the owner of the venue decides to do the only logical thing: squeeze everyone in and give them all 2 minutes. Walt Braley and Andrew Shipman bring their rapid fire style of comedy to life in this character showcase featuring sketch, improv, special guests and costume changes...lots of costume changes.

Revolving Door

Thursday

5/14

9:30 PM

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

Hitch*Cocktails

Friday

5/15

9:30 PM

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.

Trigger Happy: Annoyance's Signature Improv Show

Saturday

5/16

7:00 PM

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/

Best of Annoyance Sketch

Saturday

5/16

9:30 PM

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

Cheesie's: A Sitcom Pilot Staged Reading

Sunday

5/17

3:00 PM

The late night staff at a local grilled cheese restaurant in Chicago allow their personal lives to run amuck in the workplace. A workplace sitcom pilot written by Chris Jowett. This one-night only reading is to present this pilot script to gauge the strength of the script and raise money to finance the making of the pilot.

Short Form Improv Jam (Student Show)

Monday

5/18

8:00 PM

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!

Motorcycle Rocketship

Thursday

5/21

9:30 PM

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.

Spitball

Sunday

5/24

6:30 PM

Spitball is a new monthly sketch show presented by The Annoyance Sketch team, Shake the Baby. Every month the cast will produce a mix of digital and live sketches and showcase up and coming comedians and filmmakers. VIDEO SUBMISSION FORM: https://forms.gle/WsgMW8xZk5jzrkym7

Insignificant Mile

Wednesday

5/27

9:30 PM

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!

Halfway to Fifty...5

Saturday

5/30

7:30 PM

Laura is back and older than ever. Join her as she looks back on her 29 years of life through stand-up comedy, music of all genres and self- deprecation. After performing iterations of this show for the past four years, Laura is thrilled to be bringing her life back to the stage. Laura is a recent winner of Best Comedian (Non-Standup) from the Chicago Reader. She has been at The Annoyance, iO, The Second City, Zanies, The Laugh Factory and Lincoln Lodge. Steve Cochran also deemed her a "Comedian To Watch." Come see stand up comedy and live music weaved together in a way that will make you wonder, "Was that really necessary?" The show will also feature the blessing of world famous music director, Micky York. The sassiest stand-up in Chicago, Joe Nicastro, will open. What more could you ask for? Probably a lot- but that doesn't matter. Just come!

Mud City Improv Festival @ The Annoyance

Thursday

6/4

9:00 PM

Mud City Improv Festival is an annual Chicago-based improv festival that connects college improv teams to the Chicago improv community. This year’s festival will take place June 4th-6th at various venues in Chicago, with three nights of performances, workshops with veteran improvisors, and the opportunity to meet other college improvisors from across the country.

Escapades!

Friday

6/5

9:30 PM

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!

The Soccer Show

Saturday

6/13

10:30 PM

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!

All Four Seasons: Pride Night

Wednesday

6/17

9:30 PM

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.

Music Flows Through Us Like a River

Wednesday

5/13

8:00 PM

Comedians and chosen ones: Abby Rankin and Max Balderston, enlighten audiences through a series of comedic sketches, music, and heartfelt truths about the universe. In the end, Abby, Max, and director Aidan Tappert, hope you walk away from this experience one hour older and wiser.

Cryptic

Thursday

5/14

8:00 PM

When you see Cryptic, you get the full scoop behind a mysterious paranormal event. Our cast creates a fully improvised documentary, complete with interviews, theories, accusations, and revelations to show you the relationships and intrigue behind this definitely real mystery. From urban legends to cryptid sightings, from abductions to encounters - if you love true crime and tall tales, you'll love Cryptic (a Time Onion production).

Missed Call

Friday

5/15

8:00 PM

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

Holy Fuck Comedy Hour

Friday

5/15

11:59 PM

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.

Father Figures

Saturday

5/16

8:00 PM

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.

To What End? Comedy Variety Hour

Saturday

5/16

10:30 PM

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!

Semicolon Parenthesis

Sunday

5/17

8:00 PM

Semicolon Parenthesis is a sketch show with comedians Evelyn Mae and Connor Snow, two former Southerners from Kentucky & Texas respectively. Consisting of optimistically absurd relationship sketches, solo character monologues, offbeat improv shells, and the occasional song, this sketch show is less sketchy and more like a journey with good pals filled with whimsy and most importantly love.

Improv - Student Jam (Student Show)

Monday

5/18

9:30 PM

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.

Voila! The Improvised Musical

Friday

5/22

8:00 PM

Voila! The Improvised Musical unleashes a unique style of musical improvisation born in the heart of the Chicago comedy scene. This fearless cast spins sharp-witted scenework into showstopping numbers, keeping the melodic madness in perfect tempo. This show samples styles from your favorite musicals, neat and with a twist on the Great American Songbook. Catch Voila! The Improvised Musical on the Annoyance Theatre Mainstage, Fridays May 1, 22, and 29th at 8pm!

Hail Marys

Sunday

5/24

8:00 PM

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!

Blue Velvet Lounge

Friday

5/29

6:00 PM

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.

Better

Sunday

5/31

8:00 PM

Raised religious, wired anxious, diagnosed obsessive, trained in pointe work with a heaping sprinkle of golden age musical theatre, and working a STEM day job, Thea L. Anderson is a consummate devotee to getting Better: a dedicated pursuit of the list of tasks that, when completed with diligence and focus, get you where you want to go - whether that means hot, holy, talented, safe, loved or successful. This show is a solo musical about what happens when trying to become better fails - or when it succeeds in ways you couldn’t predict and aren’t prepared to handle.

Historically Inaccurate

Thursday

6/4

9:30 PM

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.

Cafe Lounge Underwater

Thursday

6/11

8:00 PM

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!

Single Sided

Monday

6/15

7:30 PM

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.

Party 4 U (For Me)

Friday

7/10

8:00 PM

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

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