What I Like About You: 6 Improvisers I Admire

Working with great improvisers is exciting and fun, and usually I ended up learning a lot from them.

Over the years I have been fortunate enough to get to play with some of the best improvisers out there, and because I am still doing Jimmy and Johnnie on Zoom, I still get to do so.

Here are six improvisers (believe me, there are tons more), that I have learned from and the traits of theirs that I would love to have.

  1. Kevin Dorff
    Back in the ’90s, before the “the game of the scene” was even a term, Kevin was living it. Maybe it was because he was such a great chess player, but you couldn’t do a scene with him without him finding “the game” in a nanosecond. He made it look so easy, and made it easy for me to the find it as well.
    What Kevin Taught Me: The game is enough to sustain a scene
    Trait I Would Like to Have from Kevin: Finding the game
  2. Susan Messing
    I have known Susan for over 30 years. We first met when we were in our 20s back at the ImprovOlympic. Besides having instant chemistry with her, I feel when I play with her, I always I follow her lead. She is fearless and plays some of the most unusual, out-there characters.
    What Susan Taught Me: “If I am not having fun, I am the asshole.”
    Trait I Would Like to Have from Susan: Her fearlessness
  3. Joe Bill
    I have known Joe almost as long as Susan, and what makes Joe such fun to work with is his proficiency in all styles of improv. Joe has tremendous range as an improviser and he’s easy to work with because he always meets you where you’re at.
    What Joe Taught Me: It’s not about me
    Trait I Would I Like to Have From Joe: His agility
  4. John Hildreth
    When it comes to finding a character’s point of view organically, John is a genius. I mean this, he is a genius. John can find a unique point of view for his character in the first couple lines of a scene. It’s amazing because he can do it so effortlessly, and his characters always generate huge laughs. And he does it by getting it all off of his scene partner.
    What John Taught Me: To pay even more attention to my partner at the top of the scene.
    Trait I Would Like to Have From John: Finding my character’s point of view
  5. Jay Sukow
    When it comes to improvising, Jay is all about fun. He is Dr. Fun, Mr. Positivity, and The Duke of Yes, And. When I play with Jay, the fun is contagious and even a sourpuss like myself can’t resist joining in.
    What Jay Taught Me: Be positive and say Yes, And more often.
    Trait I Would Like to Have From Jay: Joy
  6. Michelle Gilliam
    Recently, I played with Michelle on Zoom and I was blown away by her patience in building a character and scene line by line. She takes her time, and because of that, her relationships and scenes have real substance. She brings a strong acting background to her improvising, too, which means she is not afraid to access her emotions or vulnerability.
    What Michelle Taught Me: To slow down even more and trust your partner even more.
    Trait I Would Like to Have From Michelle: Patience

Who are some of your favorite improvisers, and what do you admire about them? Tell us in the comments below.


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254: Why is Chicago the Mecca of Improv?

Jimmy is really proud to share with you this piece he did for Curious City on WBEZ, Chicago Public Radio, answering the question, “Why is Chicago the mecca of improv?” In this episode you will hear several people’s theories about why this is. Jimmy interviews old friends TJ Jagodowski, Susan Messing and Jonathan Pitts to get their input. This is a must-listen for any improv nerd, and Jimmy secretly hopes after you listen to this episode you move to Chicago.

Why is Chicago the Mecca of Improv?

Have you ever thought about why Chicago is the mecca of improv? Well, I recently had the chance to explore this question in depth when WBEZ, the public radio station in Chicago, contacted me about doing a story about it for their Curious City show.

If you ask me, Chicago really has all the right elements for making it the perfect destination for improv. I First of all, for a major city, Chicago is an affordable place to live on what an improviser makes at his or her temp job while taking classes and running around town doing shows.

Secondly, you have the history of improv here, plus so many different improv schools and performance opportunities, and of course, the genuineness of Chicagoans makes the people in the improv/acting community beyond supportive. Plus, there is a deep respect for craft here. There is no show business pressure here, so the stakes are fairly low, which makes it a great place to create, take risks and make lasting friendships.

In the story, however, we wanted to get some other people’s thoughts on why Chicago has become an important destination for improvisers, so I interviewed Susan Messing, TJ Jagodowski and Jonathan Pitts to get their thoughts on this as well.

Here’s a link to the final story. I’d love to know why you think Chicago is the mecca of improv, too.

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.



Improv Night with Sand and Spitballin’
Quenchers Saloon
2401 N Western Ave.
8 p.m.

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.

iO Chicago’s Mission Theater
1501 N. Kingsbury St.
10 p.m.

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.


Sears Tower
iO Chicago’s Del Close Theater
1501 N. Kingsbury St.
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.

iO Chicago’s Del Close Theater
1501 N. Kingsbury St.
10:30 p.m.

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.


TJ and Dave
iO Chicago’s The Mission Theater
1501 N. Kingsbury St.
10:30 p.m.

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
8 p.m.

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.
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.


Messing with a Friend
The Annoyance Theater
851 W. Belmont Ave.
10:30 p.m.

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.


The Boys
Second City’s Blackout Cabaret
1616 N. Wells St.
9 p.m.

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.
10:30 p.m.

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.


Improvised Shakespeare
iO Chicago’s Del Close Theater
1501 N. Kingsbury St.

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.

The Chicago Improv Den
1333 N. Milwaukee Ave.
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.


Improv Nerd
Second City’s Beat Lounge
1616 N. Wells St.
5:30 p.m.

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.


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 to get the secret location for their next show.



Going Outside of Improv To Get Better At Improv

Lately, I have been trying my hand at stand-up and storytelling, doing some open mics around the city. So far, the results have been mixed, but where I am starting to see it pay off is in my improv.

Doing things outside of improv only makes you a better improviser. A lot of times I think that when I’m in a rut or have had a series of bad improv shows, the answer is to force a solution and just work harder. But the truth is, more improv doesn’t necessarily make me better. Sometimes it makes it worse. That is when I need to go out and do something that brings me joy so I won’t put so much pressure on myself when I’m doing improv.

I need to remember that it’s important to be filled up creatively, not only for my improv, but also for my teaching, and if you ask my wife, my life. Yes, I am easier to be around when I am creatively fulfilled. Having another creative outlet gives me more to give to my classes, to my scene partners on stage and to the audience, as well.

For me, I feel creatively fulfilled when I’m expressing myself, and sometimes improv can do that for me and sometimes it can’t. Any art form has its limits, and I get in trouble when I think I can get all of my needs met in one place. That is when I get stuck and frustrated.

That is what was starting to happen. Most of the time when I was doing a live version of Improv Nerd, I was making it life or death. I was putting way too much pressure on myself – all because I wasn’t allowing myself to have enough fun in the rest of my life. My whole life was serious, so my improv became serious, too.

Then this summer, I decided to take a stand-up class at the Lincoln Lodge. I spent time writing my set and perfecting my delivery. This led me to doing a few storytelling events at The Abbey Pub, Louder Than a Mom, and Surprise Party. And suddenly, out of nowhere, improv started to feel fun again, and isn’t that the point of all of this stuff anyway?

This past Sunday I had one of the best times I’ve had at an Improv Nerd show in a long time. Then after the show, I had to drive to Second City to celebrate the third year anniversary of a little improv show called “Jimmy and Johnny” that I do with the super talented John Hildreth. Each month we ask a special guest to join us to improvise. Our guest this time was one of my favorite people to improvise of all time: Susan Messing. We have known each other for more than 25 years and I love her. Of course, those two were great as always, and even though I thought I was a bit off, I had a blast working with them.

I actually came home that night feeling invigorated and, dare I admit it, happy. (No, not a typo or misprint. You read it right, happy.) That was the direct effect of me finding a way to fill my need for creativity outside of improv. Now, I just have to keep remembering it.

Don’t forget to get a copy of Jimmy’s new book, The Inner Game of Improv! Now available as a PDF or for Kindle at Amazon.

3 Tips for Creating Instant Improv Characters

By far the thing I hear most from improv students when they first start working with me is: “I want to do characters. Teach me how to do characters. My last teacher said I need to do more characters.”

I get it. I have struggled with this myself. There was even a time when I was convinced that I didn’t know how to play characters so I would pretend like it wasn’t cool to do them, bragging to people, “I don’t do characters.” What an idiot. In some cases, I actually was doing them and didn’t even know I was, and the rest of the time I was judging myself and others for doing them. I was messed up.

Thank God over the years I have gotten more comfortable with playing improv characters, and now I find it fun and liberating. (That’s between us). I have come across some simple tricks to jump start me into doing characters. You are going to hate me for this, but there is no right or wrong way to create characters. It’s really whatever works for you. I have seen people approach character by a playing an attitude, or an emotion, or a physicality or a voice or an accent. All work, it’s just a matter of taste. What is important in playing improv characters is point of view, how they look at the world and how they respond to their scene partner through that filter.

Once I have that filter in place, and know how this person will respond to things, I am out of my head and I can start saying things that I would not normally say on stage or in life. I’m not playing me anymore. I may be a heightened part of me or someone completely different. All I know is it is so fucking freeing when it happens.

Here are three of the quickest way to create instant character:

1. Start with a strong emotion
That’s right. Come right out of the box and start the scene with a strong emotion: happy, sad, angry, afraid. I know what you are saying: “That is cheating. That is planning.” You are not planning the scene, you are not planning the dialogue, you are still improvising. Get over it. Nobody has time in most long form scenes to start out in neutral. You have to start with something or you’re dead. I have seen beginning students who were completely paralyzed on stage, until I introduced this concept and they were able to do scene work that took me ten years to achieve. A strong emotion will give you an instant point of view. End of discussion.

2. Mirror your scene partner
I love working with Susan Messing because nobody does strong characters like she does, and I am sharing with you a little secret that I use when I play with her. I just follow her and mirror what she is doing in terms of energy and character. (Let’s also keep that between us). I can hear you guys now: “But Jimmy, you are working with Susan Messing. She is brilliant.” Before you are so quick to judge, try it. I have often mirrored characters, and I have seen my students do it with tons of success. Why can’t you? When John Hildreth and I do “Jimmy and Johnnie” we usually agree before the show that we will start our first scene by mirroring everyone else’s energy and characters. We built that right into the form. Thank you Susan and Rachael Mason for that one.

Another variation on this is to play the opposite of your partner’s energy from the instant they come out on stage. If some comes out and plays a big, boisterous character, you could play the opposite — a meek or scared person. Either way, you’ll have a distinct point of view. I think you get it, so let’s move on.

3. Using a physicality
You’ve heard this one a million times, I am sure, and I have used this one a lot over the years. The secret to this is to be aware of what you are doing and then heighten the shit out of it. This typically comes from a very organic place. You may start the scene by wringing your hands together. What does that tell you about the character? They could be nervous or anxious. They could be washing their hands and being a germ-a-phobe. Ok, right now start rubbing your hand together and see what kind of attitude comes up for you. I’ll wait.

Another simple variation of using a physicality is adjusting your posture. I have done this where I simply adjust my naturally poor posture. If I enter a scene where I am standing up straight, I immediately play high status: a boss or a teacher a bully or an asshole father. I have gone into scene where I bend over and up play some sort of wimp or weasel or snitch or low self-esteem guy.

What do you use to create instant characters? Let us know. I am always open to keep learning more.

Don’t live in Chicago? Take a trip to Chicago for Jimmy’s Art of Slow Comedy Summer Intensives July 27-28 or Aug. 10-11. Sign up TODAY!

Facebook intervention

I have been involved in a bit of controversy around some of my Facebook posts. I have heard through others people that some of my friends are concerned, they think I am ruining my reputation, sharing too much information or having another break down.

On the most recent episode of Improv Nerd podcast, we turned the tables and had Susan Messing interview me, and during the interview, she confronted me on my polarizing Facebook posts, asking me why I was writing them.

If you haven’t been following me, here’s an example of what I’ve been writing. I’ve posted some self-loathing stuff like “I have been so busy lately, I have not found any time to hate myself” and “To all of the women I keep turning into my mother, Happy Mother’s Day,” to more positive posts like “Brilliance coming soon” or “When is someone going to realize how deep I am and offer me a book deal off my Facebook posts?”

Some days I have posted several times in a row, all about how I wished Facebook would make me feel better or how I have so much shame.

When Susan asked me about why I am writing these kind of posts, I wish I had not been so defensive and had given her a different answer. The one I would give today would be “I don’t know.”

When I put a post on Facebook, I sit at my computer screen and it’s like I go into a persona, much like when I am improvising a character, and I lose myself, saying things through the character that I am afraid to say in my boring everyday life.

After the show on the car ride home from Stage 773, my wife, Lauren, confessed that she did not get some of my Facebook posts. My producer called me and, like Susan and my wife, thought I should put the energy I am putting into Facebook and write a new one-man show. I felt ganged up on: This was a Facebook intervention.

I have written many solo shows and each process has been different. And maybe this is my process for writing another solo show or a book or a screen play. Who knows? All I know right now is that my voice is getting stronger and I am having fun. I learned a long time ago at the Annoyance Theater that product follows process, and not the other way around.

I will tell you this whole “Facbookgate” has left me confused and kicked up my people-pleasing, which has always held me back since I was old enough to express myself. When I post now on Facebook, I second-guess myself, and before I write something I think, “What will people think?”

This is death for any artist in any field. I want the people-pleasing to go away, and I want to care less about what people think of me. If I am going to continue to grow as an artist, I need to be comfortable in making people uncomfortable. I hope I have your blessing.

How to Deal with Fear Before a Show

How to Deal with Fear Before a Show

Long-Form improv classesFear before a show is unpredictable. Sometimes I have it, and sometimes I don’t. Last month, I had it before doing “Messing with A Friend” with Susan Messing.

I love Susan as much as a person as I love playing with her. Having Susan ask me to play with her in her improv show is not only an honor, it’s a joy.And that’s where the fear comes in. Any time I’m afraid I’ll lose something that brings me joy, my thinking goes a bit wacky. The day of the show, I started having thoughts like this: “I am going to have a bad show. It’s going to be so bad that Susan will never ask me to play with her again.”

As I went through the day those thoughts became a mantra and that mantra was dangerously close to becominga self-fulfilling prophecy if I didn’t do something about it.

By the afternoon, I was still not in enough pain to tell on myself.  I have a high tolerance for pain and anxiety.So, finally at dinner that night, I told my wife all my doubts and fear about the show that night. My wife Lauren, is wise and supportive and smart, and she just listened, and didn’t try to fix me or worse tell me that I should not feel what I was feeling, which always leads to shame. Immediately I felt some relief, because as painful as it was, I had admitted it, and that helped. But the show wasn’t until 10:30 p.m. I had four more hours to go, and I wasn’t sure how long my good feelings would last.

They didn’t. A half hour before the show, my head filled up with those thoughts again: “I know this show is going to suck. Susan will never have me back. It’s over.” I sat in my car outside the Annoyance Theater on Broadway Avenue, in the seedy north side neighborhood of Uptown in Chicago, and called my friend Ryan. Like my wife, Ryan is wise, and supportive and listened, giving me encouragement, but mostly talking me off the ledge. After a couple of minutes, I realized the ledge was only about three feet off the ground. Most importantly, at no point in our conversation did he say “Don’t be afraid” or “You shouldn’t be afraid.” I don’t call people anymore who say that kind of shit, unless I am trolling for shame.

When it comes to fear about performing, I think we have it all wrong. You can’t deny your fear or just snap your fingers and get rid of it. We’ve got to acknowledge it, so we can use it. Del Close used to say “Follow The Fear.” He got it — we have to admit that we’re afraid first before we can follow it.

When I first started dating Lauren, I was scared to have sex with her. I had all sorts of reasons to be afraid: my lack of experience, my fear of intimacy, fear of getting her pregnant. I know it’s nuts. At the time, my crazy therapist gave me a bit of advice “While you’re having sex, tell her that you are terrified and you want her to keep going.”

This is no different than improvising. Admit you are terrified and keep going.

After getting off the phone with Ryan, I entered the theater, and when we did the show that night it was great, and I realized a big part of the reason it worked was because I had let go of the fear by talking about it with other people.

Martin DeMaat, one of my favorite improv teachers, used to come backstage before a show and hold both hands out and say “Here, give me your fear.”You would then pretend you were handing him over your imaginary fear. It was incredibly hokey and something my friends and I would make fun of him for when we were doing our Martin imitations, but the truth is I do it too by telling people I am afraid.

Over the years I have seen students struggle with fear before a show, especially in my upper level improv classes when they have to perform a long form show for family and friends on the last day of class. Instead of admitting they are afraid, sometimes students end up quitting a class or two before the performance. It’s sad. I wish they knew that it’s normal to be scared and by just showing up, they are succeeding.

And maybe the next time I do Messing with A Friend, and believe me there’ll be a next time, I will be brave enough to share my fear with Susan.