Summer Intensive Student's Guide To Navigating the Scene

By Dillon Cassidy


Here are a few recommendations of shows to see if you’re trying to get a full taste of what the Chicago scene has to offer. This is a short list of shows compiled by me, a person that has been in the scene for five or so years now, that I truly enjoy and would recommend to anyone to see, but especially someone with an interest in improvisation.

The Shithole - Sundays at 8PM - Location TBD

Never have I felt more like I am at the set of a movie, than when I am at the Shithole. This show embodies what I think is great about the scene in Chicago. It’s an incredibly infectious and supportive vibe, filled with present people who just want to make art. It’s also kinda of a secret, so you’ll have to do some digging online to find this show.

Matt Damon Improv - Sundays at 9:30 - The Annoyance

I’ve seen this folks absolutely slay a number of times all over the city. This group of women of color sometimes invites a white man (Matt Damon), or woman (Lena Dunham) to come play with them. Either way, they always deliver.

Dynasty - Mondays at 8PM - iO Chicago

This is a show that iO champions, and rightly so. It’s great. The cast is great. The feelings are GOOD. It’s a show that matters. Basically every Monday I’m not doing something else, I find myself saying to myself ‘I should go see Dynasty,’ and you should too. =)

The Show - Mondays at 8PM - The Crowd

Okay, so full disclosure, this is a show I produce, so I am shamelessly plugging it. But I do think it’s interesting. This show is done live and broadcast to our twitch channel (so if you like it, you can still see it after you go home). It’s a rotating cast of Chicago teams, closed out by the cast of the The Show.

Super Human - Tuesdays at 9:30PM - The Annoyance

I admire this cast so gosh darn much. Everyone in this show is someone that I came up watching, and they are all immensely talented. You are wasting your time in Chicago if you don’t see this team at least once.

Fudge - Tuesdays at 8PM - iO Chicago

A lot of people are tired of seeing teams comprised entirely of men, but these guys are really doing something special. Fudge is a team I really really love watching right now, and I’m looking forward to seeing what they grow into during their tenure in Chicago.

Preach - Friday at 8PM - iO Chicago

Improv is a naturally volatile form of performance, which means people experiment with it. Sometimes it works, sometimes it doesn’t. Preach is an example of it working incredibly well. This is truly the most fresh improvised work I have seen in the five years I’ve been consuming comedy in Chicago.

The Holy Fuck Comedy Hour - Fridays 11:59PM - The Annoyance

This is the only show on the list I haven’t actually seen, and to be honest it’s a huge pitfall of mine. BUT, I don’t think any list of Chicago comedy shows would be complete without what is widely considered to be a staple of the scene, and a show that sits of the forefront of folks minds when they think about the Annoyance.

House Team Night - Fridays at 10:00PM - The Crowd

Definitely putting the horse before the wagon here, but we’re really excited about this show. It’s something new. Each team has a different vision, varying from new media to movement to sketch. It’s the Crowd’s take on what a House Team Program could look like.

The Showcase -  Saturdays at 10:30PM - CIC Theater

I’ve said this before, and I’ll say it again. I believe CIC has the highest quality house teams out of all the theaters in Chicago. This is a showcase of those teams, it’s a must see. Personally, big fans of Little Gary, Majority Rules, and Cashel (also see my team Great Lakes Activity Center).

Infinite Wrench - Fridays, Saturdays, Sundays - The Neo-Futurists

I wanted to include this show because I think it’s great. It’s not really a part of the comedy scene, but it’s a comedy show - kinda. It’s a lot more theatrical. It’s a show that will challenge what you think about comedy shows, and probably inspire you to do something different.


Ya baby! This is what we’re really all here for. Let’s talk about where you can show up and get up on stage that night. I’m a little bit removed from this part of the scene, so if you know of any other jams or performance opportunities that would help flesh out this list please leave a comment and we’ll try to update the list!

The Mixer - Mondays at 10PM - The Playground

This is such an absolute fixture in the comedy scene. It’s a show that does not get enough love. The guys that run this are so wonderful and generous with their time and energy, and I have a big crush on all of them. Just show up, get put on a team, do an improv lesson, and then perform. Come every week.

BYOT - Tuesdays at 10PM - The Crowd

BYOT has been running at the Crowd for a little over a year now, to usually way to packed a house. The energy in the room is great and supportive. Everyone is there to have a good time. Grab a group of friends from your intensive class, show up, drop your name in the bucket, and get up on stage!


If you’re here, why not dive head first into the ~community~!! Okay, so here’s some stuff to do that is either based around the improv community, but isn’t necessarily a performance, OR just some cool Chicago stuff to do.

The Crowd’s Mandatory Block Party - Saturday, July 14th at Noon

We’re throwing a block party on Dakin Avenue to celebrate our community and enjoy the summer while it’s here! We’ll be grilling, face painting, drinking, and generally having a good time and talking about stuff. You’re all more than welcome to come by and hang out as well.

Midnight Movies at the Music Box - Varied

These are just so gosh darn fun! If you’re looking to do something that is a little bit different than improv, bring some friends and check out a midnight movie at a beloved art institution in the city.

Chicago Hot Dog Fest - August 10-12

The only other thing that Chicago is known for, besides improv, is hot dogs! Invented at the 1983 Worlds Fair, the hot dog is a Chicago staple and is best enjoyed with NO FUCKING KETCHUP. $5 suggested donation.

See a baseball game! - Varied

Chicago has not one, but two baseball teams. One is good and one is not. What the White Sox lack in onfield talent, they make up with cheap tickets, fantastic food and you can get 24 ounces of Modelo for just $12.50. The Cubs are also a team. Both teams are right off the Red Line and offer great venues to do bits at.