Tuesday Musical Improv

Dec 9, 2025 - Dec 30, 2025

The Annoyance’s very own musical ensembles. They sing funny songs. Off the top of their heads. Every Tuesday at 8.

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Improvised Christmas Carol

Dec 10, 2025 - Dec 21, 2025

Usually, at this time of year, Ebenezer Scrooge learns the true meaning of Christmas. Funnily enough, trios of Christmas ghosts regularly haunt all kinds of grumpy people – and you get to watch it happen live! Back by popular demand, each 45-minute show of An Improvised Christmas Carol drags a new curmudgeon – who hates something the audience loves – through a hilarious journey of self-reflection. You’ll laugh, you’ll gasp, you’ll sing along! This holiday season, pull up your easy chair, grab a mug of hot cocoa, and don’t miss the cozy, fully improvised, made-for-television-but-appearing-on-stage special that is An Improvised Christmas Carol!

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Cafe Lounge Underwater

Dec 11, 2025 - Dec 18, 2025

Start your weekends early with Cafe Lounge Underwater, Thursdays at The Annoyance!


Cafe Lounge Underwater is a sketch show that feels like a great house party. There’s dancing, music, drinks, and of course, laughs. Join Caroline Burke, Tom Phelan, and Maryrose Sheridan as they perform sketches from their monthly show run!


After two sold-out runs at Chicago’s Annoyance Theatre and features in the Chicago Sketchfest and Miami Improv Festival, Cafe Lounge Underwater brings a brand new show that will have you asking, “when can we all hang out next?”

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Gifted Children: Winter Break

Dec 11, 2025 - Dec 18, 2025

Gifted Children Winter Break is a three person holiday sketch show from AJ Hernandez-Sortore, Alex Limarzi, and Miranda Bianchi. The Gifted Children will take you on a winter wonderland journey through Santa’s Workshop, Whoville and of course, a really big hill. This show will have 100s of festive lines, and presents for all!

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Fishbowl by Sight Unseen

Dec 11, 2025 - Dec 18, 2025

Fishbowl hosted by Sight Unseen is 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. The night closes with a set from Sight Unseen – an Annoyance house team that prides itself on being equal parts heartwarming and offensive.

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Blue Velvet Lounge

Dec 12, 2025 - Dec 19, 2025

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.

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A Very Steamworks Christmas

Dec 12, 2025 - Dec 20, 2025

Oh, we’re keeping the yuletides GAY! Join us for a queer take on the classic A Christmas Carol as some of your favorite characters from the hit summer show “Steamworks the Musical” navigate the past, present, and future while trying to save the building from being destroyed by an evil Grinch! 


Written by Connor James Hirsch, Noah Lanos, Nathan Wetter, and Ryan Brown , “A Very Steamworks Christmas” is coming back for its second year after a sold-out run in 2024. 

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Missed Call

Dec 12, 2025 - Dec 19, 2025

Brand new sketch comedy every week from one of Chicago’s premiere sketch teams.

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Hitch*Cocktails

Dec 12, 2025 - Dec 26, 2025

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock.

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Baby Wine

Dec 12, 2025 - Jan 30, 2026

A lgbtqia+ themed variety show featuring some of Chicago’s strongest and most diversely hilarious voices!

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Holy Fuck Comedy Hour

Dec 12, 2025 - Dec 19, 2025

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.

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Oy! : A Holiday Show for Everyone

Dec 13, 2025 - Dec 27, 2025

What even is Hanukkah? And how the hell do you spell it?? “OY!” is back with sketches, songs, and improv from an all-Jewish cast exploring the customs and cultures that bring Jews together all over the world, while also celebrating Jewish joy and traditions. So get off your tuchus and come celebrate the holidays with us!

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Trigger Happy: Annoyance's Signature Improv Show

Dec 13, 2025 - Dec 27, 2025

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

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Fire & Beer

Dec 13, 2025 - Jan 3, 2026

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.

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Best of Annoyance Sketch

Dec 13, 2025 - Dec 27, 2025

An hour long comedy show featuring some of Annoyance Theatre’s best and funniest.

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We Took Edibles an Hour Ago

Dec 13, 2025 - Dec 20, 2025

A bunch of grown-ass adults get high and play make believe.

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