The critically acclaimed original musical returns one more time to the Annoyance Theater just in time for the holiday season. Come enjoy some of Chicago’s biggest up-and-coming comedic performers in this heartfelt parody inspired by all of your favorite orphan media, from classic stories like “Annie” and “Oliver”, to more recent tales like Harry Potter and Batman.

"Little Orphan Boy the Musical!" follows the uplifting tale of a Little English Lad who has lost his Mum yet again, this time in the city that never sleeps, New York, baby!

See why critics are calling it, “stupid done smart” (Chicago Reader), “laugh out loud funny” (Newcity Stage), and “on the cusp of becoming a huge hit” (Rikki Lee Travolta). You’ll find yourself singing these songs for weeks after joining a little British lad on his search to find his mum in NYC. PG-13 due to language, some material may be inappropriate for children under 13.

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

BABY WINE is one of Chicago's longest running LGBTQ+ comedy variety shows. Hosted by Baby Wine's core ensemble, each week a rotating lineup of queer performers open the show with a variety of acts ranging from standup to sketch to music to improv to drag. Baby Wine closes out the show with a no holds barred, long-form improv set. Come lol with us babe!

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.

The Teeny Tiny Character Show is just that: a petite little space for comedians to showcase their characters. Will and Rachel will guide some of Chicago’s best performers through a night of miniature monologues and itty-bitty improv. Join us for a small night of big laughs. Let’s get little!

Motorcycle Rocketship is more than just a hilarious sketch show with new material every week. It’s a journey through the zeitgeist of culture. It’s a psychedelic submarine swimming through an ocean of ideas. It’s a really big box with a smaller box inside of it, and inside of THAT box? Laughter. So strap in for the ride of your ride of your life, sweet chunklets, because this motorcycle is rocketshipping all the way to the bank.

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!

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.

In this world-premiere comedy from the comedic minds of Sage Huston and Riley Woollen, holiday cheer meets absolute chaos as three families are trapped in the Houston airport on Christmas Eve. Complete with an impressive ensemble of Chicago comedians, stakes reach Lord of the Flies-esque highs as loyalties are questioned, sanities challenged, and lives at stake. Can this Christmas be saved, or is it…terminal?

In “David & David”, audiences will be delighted (and a little confused) as they are welcomed into 123 Main Street, the brownstone apartment of the titular roommates David Byrne and David Lynch, played by David Lynch and David Byrne, reverse respectively. First performed at The Annoyance as a sold-out test show back in December of 2023, David & David is an exploration/parody/send-up of 80’s sitcoms that promises to make you (and the pre-recorded live studio audience) laugh, applaud, whistle, and cheer.

CW: Fake gun (and accompanying single gunshot sound effect), mentions of self-harm, and dramatized violence

This 45 minute, scripted sketch revue blends the creative brain juices of comedians Joe Cariola
and Gabby Seed. Watch Gabby uncover the grounded side of unhinged characters while Joe
explores what it really means to absolutely lose it. Character-forward, absurdist, and
big-hearted, “Double Trouble” is the perfect antidote after a long week of day-trading, farting
through cold calls, and trying not to sleep at work.
Created by Lexi Purvis (director, writer), Gabs Lopez (producer, writer), and Gabby Seed
(producer, writer).
Starring Joe Cariola and Gabby Seed.
Consulting director: Leila Gorstein.
Follow the show on IG @doubletroublechicago.

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/

The critically acclaimed original musical returns one more time to the Annoyance Theater just in time for the holiday season. Come enjoy some of Chicago’s biggest up-and-coming comedic performers in this heartfelt parody inspired by all of your favorite orphan media, from classic stories like “Annie” and “Oliver”, to more recent tales like Harry Potter and Batman.

"Little Orphan Boy the Musical!" follows the uplifting tale of a Little English Lad who has lost his Mum yet again, this time in the city that never sleeps, New York, baby!

See why critics are calling it, “stupid done smart” (Chicago Reader), “laugh out loud funny” (Newcity Stage), and “on the cusp of becoming a huge hit” (Rikki Lee Travolta). You’ll find yourself singing these songs for weeks after joining a little British lad on his search to find his mum in NYC. PG-13 due to language, some material may be inappropriate for children under 13.

CHIP Chats is a PowerPoint comedy show loosely based on TED Talks- but where TED stands for Technology, Entertainment, and Design, CHIP stands for Comedy, Hilarity, Insanity, and Pointlessness- and we deliver on those promises. We here at CHIP Chats can guarantee that by the end of every show you will either learn something or not! Like TED Talks, but much Worse.

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.

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

A night of Roman fuckery. Watch philosophers roast each other, improv gladiators battle, and kneel to Cesar in this truly unruly night of alt-comedy.

In the world of improv comedy, anything can happen. But what happens when all the decent folk have left and a cast of delirious performers take over? After Hours Improv is The Annoyance's late night non-so-secret show where only the dumbest and most daring bits can truly be given the space they deserve...After Hours

Max and Annie invite you into their shared unconcious! Each performance showcases a premiere improv opener from the Chicago area, followed by sketches featuring absurd and wild characters performed by Max and Annie, and capping off the night is some high-octane improv with Max and Annie and a special guest. You will walk away with two thoughts: 1. Wtf did I just watch? And 2. Why did I freaking love it so much?
***Max and Annie are not affiliated with any political organization***

Treat yourself to Chicago’s most intellectual comedy show. Comedians of all kinds going on about books while sipping very high end beverages. Bring your date to impress them, or come alone to feel self important.

It's Christmas at Steamworks, and all through the baths, all the gays are celebrating, and there are ghosts?! Join us for a queer take on the classic A Christmas Carol as your favorite characters from Steamworks the Musical navigate Steamworks' past, present, and future while trying to save the building from being destroyed by an evil Grinch! We promise you lots of raunchy reimaged Christmas carols, all while keeping the yuletide gay!

What even is Hanukkah? And how the hell do you spell it?? Enjoy scenes, songs and improv from our all-Jewish cast as they explore the customs and cultures that bring Jews together all over the world. Join us for this delightful holiday party that remembers the holidays are for everyone, and celebrates Jewish joy and traditions.

Join Ryan & Allie for their 4th Annual Christmas Extravaganza! For One Night Only, join the Live Studio Audience for this sensational, breathtaking, wondrous, thrilling, splendid, remarkable, striking, astounding, fantastic, magnificent, dazzling, amazing, astonishing, marvelous, stunning, dramatic, miraculous, fabulous, grand, eye-catching multimedia theatrical experience! This is a show that you won't want to miss!

The critically acclaimed original musical returns one more time to the Annoyance Theater just in time for the holiday season. Come enjoy some of Chicago’s biggest up-and-coming comedic performers in this heartfelt parody inspired by all of your favorite orphan media, from classic stories like “Annie” and “Oliver”, to more recent tales like Harry Potter and Batman.

"Little Orphan Boy the Musical!" follows the uplifting tale of a Little English Lad who has lost his Mum yet again, this time in the city that never sleeps, New York, baby!

See why critics are calling it, “stupid done smart” (Chicago Reader), “laugh out loud funny” (Newcity Stage), and “on the cusp of becoming a huge hit” (Rikki Lee Travolta). You’ll find yourself singing these songs for weeks after joining a little British lad on his search to find his mum in NYC. PG-13 due to language, some material may be inappropriate for children under 13.

See Chicago's longest-running improv team bring their unique blend of big characters and absurd situations to the stage with infectious energy. Formed in 1996, Deep Schwa has performed over a thousand shows in theaters all over Chicago and beyond. Made up of an evolving cast of ten of the city's best veteran players. Each show singular, each show electric.

Using the vehicles or Stand up Comedy, Sketch Comedy and Music The LateNight-Ish Experience will display brilliance, creativity, and community through live performances. Coupled with the preparation of comedians, singers, instrumentalists and entertainers for T.V and other live performances. This show is to showcase young professionals and dispel the common misconceptions about live performances being a thing of the past.

One Star is a Chicago-based comedy troupe that enjoys schadenfreude. We take inspiration from other people's bad (or good!) experiences. With your suggested business or location as our guide, we'll look up a real review on the fly and improvise an entire piece, hoping to transform their bad (or good!) experience into a great one for you. With two opening acts of improv, stand-up, sketch, and more, come join in the fun Mondays at 8pm!

A night for Annoyance students to JAM!

Hosted by members of Tuesday Musical Improv, this free weekly jam allows anyone to try out musical improv on the Annoyance Mainstage. Sign-ups begin at 6:45--no experience necessary!

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

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!

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!

T'was the night before Christmas, and all through the house.. Our heroine Mallory was running around and about.. After finding out her nudes were leaked online, she couldn't help but feel like this was the end of time.. It's up to three ghosts with all-seeing eyes, to help her avoid total social demise.. Will they discover the culprit behind her pain, or will Mallory spend Christmas sulking in shame?

The small rural town of Dove Cliff is at risk of being overtaken by a major tech megacorp, led by a former Dove Cliff resident with a devastating secret. The whole town comes together, led by Delilah Pearl, the artistic director of the town’s Pearl Dance Studio, to put on a Winter Extravaganza show to raise enough money to keep the takeover from happening. Supported by the town's residents and its local cryptid, Larri (with an I), they battle against the power-hungry Mayor Sharon Walker-Easton and the Dove Cliff prodigal son David Marsh McGrath, taking pledges over the phone and fielding commentary from the town residents. Will Dove Cliff be gone forever when they fail, or can Delilah and the rest of Dove Cliff actually pull this off?

In the bleak autumnal chill between Spooky Season and Happy Holidays, lies a (literal) cornucopia of chaos that some people call Thanksgiving, other people call Native American Heritage Day, and we all call “that time our parents ask us when we’re finally getting a real job and giving them grandkids!” From family feuds to fantasy football, from hometown hangouts to historical hiccups, and everything else that gets lost in the (cranberry) sauce, Andrew Baldwin and Daryn Robinson perform original comedic songs that finally answer the question, “Why are there no good Thanksgiving bops?”

Miracle at Century High School is an original Christmas musical making its world premiere at The Annoyance Theatre. When the principal of a scandal-plagued high school tasks drama teacher Jacob Lunsford with creating an original Christmas musical in order to save the school's reputation--and his job--Jacob must overcome self-doubt, chaotic students, an impossible-to-please principal, and regular visits from the ghost of Charles Dickens. Can he pull it off? Find out in this hilarious show that Saturday Night Live writer T. Sean Shannon calls "a very funny and clever new Christmas play that will jingle your bells."

Super Human is an improv team that tore into Chicago’s comedy scene in 2012 at The Upstairs Gallery (RIP). Since then, Super Human has become synonymous with bold, hilarious, fearless and fun comedy. Described as a “splash zone of women,” Super Human prides itself on the team’s diverse personalities and playing styles, with an unmistakable focus on creating inclusive learning and performance spaces. They are Super Human and SO ARE YOU!

Christmas Karen 3 is a new original multi-media play written by Elizabeth Fulton and is the trilogy no one asked for but everyone needed. Picking up one year later, Ebenezer Scrooge is stuck unable to move on after being one-upped by his own Christmas Carol storyline and no-last-name Karen grapples with the “what’s next” after she directed a hit holiday sketch extravaganza.

You’ll see some reimagined holiday characters you know and love during this feel-good play - and some not-so-holiday characters you wouldn’t necessarily expect (you’re welcome). If you didn’t see the first or second Christmas Karen, we start the play with a recap to get the whole audience up to speed. Buckle up, and help us decide if Die Hard is a Christmas movie.

Follow us on Instagram @christmas_k_3 to learn more!

A two act improv show. First, Annoyance students get a chance to enter their IDs into a fishbowl to be randomly selected to perform in an improv jam with veteran Annoyance teachers and performers. Then, the night closes with a set from Sight Unseen, an Annoyance house team who, for almost the past decade, has been known for its loose narrative form and vibrant (sometimes vicious) characters.

It's been a hell of a month! Come laugh it off with some of the best improv you'll ever see: veteran improviser Susan Messing improvises in her world renowned show Messing with a Friend with improviser Ryan Nolan. Don't miss this special event!

A tight-knit group of friends lean on each other through every 90’s New Year’s Eve – but a secret midnight kiss puts their friendships to the test.