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The Best Way to Get Out Of Your Comfort Zone

Improv is collaboration. That is why we do it, because we love to collaborate with other people. But when you have been improvising for a while, you can get set in your ways. You can start to feel comfortable only playing a certain style of improv or playing only with certain people.

I know this works for some people, but for me, it’s important to play with people who have a slightly different style than I do to ease me out of my comfort zone.

That is why I enjoy playing with John Hildreth in Jimmy and Johnnie. Although we are from the same generation of improvisers in Chicago, our approaches to the work are very different.

The guy is a genius. I am constantly trying to figure out how John comes up with a point of view so quickly at the top of every scene. I typically work slower, and I’m more serious. John brings a lot more silliness and boldness to his improv, which helps me get out of my improv rut. That is what can make it fun.

Each month, we also invite different guests to play with us, and each of them plays a different style. Though it can be scary to play with different people all of the time, it can also be fun.

Recently, we played with Thomas Kelly and Michael Brunlieb from one of the best improv groups in Chicago, Sand. They are quicker and more absurd in their play than I am, and they really know how to have fun on stage — three things I still need to work on in my improv.

I was blown out my comfort zone like with a stick of dynamite from the first scenes. The pace of the show was like a runaway freight train. It was exciting, but because I don’t usually play absurd, I spent a lot of time trying to stay on the same page with everyone. Some of the time I succeed and sometimes I was confused, and I am sure I confused them. It was terrifying and fun all at the same. I am looking forward to having them back.

When someone plays differently than we do, it’s easy to judge their style of playing and to want to look down on them. And it’s natural to want to find others who have a similar artistic sense to you to want to form a group with.

But that doesn’t mean we shouldn’t ever play with people who have different styles. Having new experiences on stage or off should be part of every improviser’s homework. That is how we grow and get better.

So, if you always play silly, maybe you should find someone who plays slow and serious to play with and see how that feels. If you only play long form, try short form. If you typically play really angry characters, find someone who can help lighten you up. You can go to an open improv jam to play with new people, or you can invite a special guest to join you in your regular show.

However you can make yourself more open to other ideas can only help you. Let me know how it goes.

Want to make improv as easy as having a conversation? Don’t miss Jimmy’s next Intro to the Art of Slow Comedy Workshop on Oct. 13!

Must-see Improv shows in Chicago this Summer

Every summer, improvisers from all over the country and the world flock to Chicago to take summer intensives and immerse themselves in Chicago’s vibrant improv scene. And every year, without fail, I get emails from these out-of-towners about what improv shows they should see when they’re here.

So this year, I thought I’d make it easy on all of you who are eager to soak up the Chicago improv scene during your summer intensives and put together a list of the best improv shows happening each night around Chicago.

Enjoy!

MONDAYS

Improv Night with Sand and Spitballin’
Quenchers Saloon
2401 N Western Ave.
773-276-9730
8 p.m.
Free

Sand is one of the best improv groups currently performing in Chicago, but to see them, you’ll have to go off the beaten path a bit. But let me tell you, the effort will be worth it. Sand performs in a bar called Quenchers, which is located at Fullerton and Western in Logan Square This three-person group is known for playing well-developed characters and not being afraid to get a little dark. In addition to the headlining act, the night also can include storytellers, stand-ups, poets, etc. Extra bonus? It’s free.

3Peat
iO Chicago’s Mission Theater
1501 N. Kingsbury St.
312-929-2401
10 p.m.
$5

If you are looking for fast-paced improv with lots of energy and pure fun then you have found it in 3Peat. Performed by a cast of incredible African Amercian improv veterans –Nnamdi Ngwe, John Thibodeaux, Patrick Rowland, Allison Ringhand, Shantira Jackson, Torian Miller, Dewayne Perkins, and Martin Morrow — you will be blown away by their amazing chemistry, commitment and yes, speed.

TUESDAYS

Sears Tower
iO Chicago’s Del Close Theater
1501 N. Kingsbury St.
312-929-2401
8 p.m.
$12 or free for iO students/performers

iO Chicago is famous for The Harold, so I would strongly suggest checking out a couple of Harold shows while you’re in town. With so many teams out there today, the trick has always been finding the good ones, and Sears Tower will not disappoint. These guys are as strong as the building they are named after.

Superhuman
iO Chicago’s Del Close Theater
1501 N. Kingsbury St.
312-929-2401
10:30 p.m.
$5

This all-women team can be perform some of the nuttiest improv out there and they are so damn funny and don’t apologize for it. This show’s a little late for a school night, so my only concern is that this high octane group may having you laughing so hard you may be tired at your intensive the next day.

WEDNESDAYS

TJ and Dave
iO Chicago’s The Mission Theater
1501 N. Kingsbury St.
312-929-2401
10:30 p.m.
$5

What can we say about the legendary group TJ and Dave that hasn’t already been said? Seeing them in Chicago where they started out is kind of like see the Pope in Vatican City; it’s a special experience that cannot missed. Since their show sells out weeks in advance, don’t delay — get your tickets now before you get here.

Virgin Daiquiri
iO Chicago’s Mission Theater
1501 N. Kingsbury
312-929-2401
8 p.m.
Free

Improvisers love to hear the word “free” when it comes to beer, food, and of course, improv shows. On Wednesday nights at iO, you get to see three Harold Teams for free, including the all-female group Virgin Daiquiri. Virgin Daiquiri is one of the best Harold teams playing today and they have such a great energy and sense play together that I am smiling just thinking about them.

Improv: Trigger Happy
The Annoyance Theater
851 W. Belmont Ave.
773-697-9693
10 p.m.
$7, $5 for students

Anything directed by Mick Napier is worth seeing, and this show is no exception. In this show, Mick combines his love of magic and improv in unrelated improvised scenes inspired by a single suggestion. This very accomplished cast of improvisers have created an invisible language among themselves that will trigger certain events during the course of the show.

THURSDAYS

Messing with a Friend
The Annoyance Theater
851 W. Belmont Ave.
773-697-9693
10:30 p.m.
$5

Susan Messing is an improv institution. In this show, Susan invites a special guest to join on stage each week, and no matter who her guest is, it’s always a great show because she’s such a damn good improviser. Her rule for her guests is simple: If you are not having fun, you are the asshole. And as someone who has played with her several times, you never want to be the asshole, which forces the guests to always bring their A games.

FRIDAYS

The Boys
Second City’s Blackout Cabaret
1616 N. Wells St.
312-337-3992
9 p.m.
$13

This show proves yes you can teach old dogs new tricks. This all-star long form group consists of some of the best improvisers and teachers here in the city: Craig Uhlir, Norm Holly, Rachael Mason, Rush Howell, Ryan Archibald and Susan Messing. They all have very different styles that mix extremely well, which can be surprising for such an uber-group. It’s some of the best old-school improv you’ll see with very impressive new-school moves that you’ll either be very jealous of or very inspired by.

Baby Wants Candy
Apollo Theater
2540 N. Lincoln Ave.
773-935-6100
10:30 p.m.
$11.25

These guys are the granddaddy of musical improv in Chicago, and what blows me away about them is the automatic agreement and support they have on stage. Their commitment is off the charts, and they make any song work, proving you don’t have to have the best singing voice to do musical improv. Even cooler? They’re backed up by a full band.

SATURDAYS

Improvised Shakespeare
iO Chicago’s Del Close Theater
1501 N. Kingsbury St.
312-929-2401
$16

To be or not to be? That is the question. And if the question is “Should I be at this show?” the answer is yes. This amazing group improvises an entire show in the style of Shakespeare, using Elizabethan English, rhyming couplets, duals, villains, love triangles and more to full effect. Trust me, you’ll be blown away.

fackBuddies
The Chicago Improv Den
1333 N. Milwaukee Ave.
773-398-7028
10:30 p.m.
$12 with an improv ID (mention Improv Nerd and get half off without an improv ID)

Dina Facklis is the founder of the Improv Den and the creator of her show fackBuddies. Like Messing with a Friend, Dina and her special guest improvise a long-form set. Dina is a terrific improviser who has the pulse of the next generation, so you are always going to see her play with some brilliant performers.

SUNDAYS

Improv Nerd
Second City’s Beat Lounge
1616 N. Wells St.
312-337-3992
5:30 p.m.
$8

Come on, you know I have to plug my own show. I’m doing two live improv shows over the summer: one on July 3 and one on Aug. 7. If you’ve never seen a live recording of my podcast, you’re in for a treat. In each episode, I interview a prominent guest in improv and then we perform a scene together and then take questions from the audience. It’s like taking a master class in one hour.

OTHER

The Shithole

This is not a show, it’s an event, and a regular love fest. The Shithole is an underground comedy show performed two to four times a week in an unknown location, usually someone’s attic or garage in Chicago. You will not find a more loving supportive crowd, and in addition to seeing improv, you’ll also see a variety of acts such as musicians, storytellers, burlesque dancers, stand-ups and more. The Shithole is an underground movement that you need to experience in person! It’s so underground, in fact, that you have to e-mail to get the info about the show. Message Shitholeinfo@gmail.com to get the secret location for their next show.