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Improv Chicago: The Windy City's Comedic Legacy

When iO Chicago and The Second City talent come together to talk shop, it's all about the laughs.

The Originals: Jim Belushi, Dan Aykroyd, Joan Rivers. The Dream Team: Seth Myers, Amy Poehler, Tina Fey. The New Wave: Aidy Bryant, Cecily Strong and Ike Barinholtz. The list of comedians who cut their teeth in Chicago and struck Hollywood gold is so impressive and extensive that you'd think there was something in our water. What's more impressive is that when we finally export our funnymen to glitzier pastures, they stay loyal. Comedic Chicago cabals have popped up all over Hollywood. Whether it's the close knit cast of HBO's hit "Silicon Valley" (stars Thomas Middleditch and Kumail Nanjiani both stomped Chicago on their rise) or power duo Keegan-Michael Key and Jordan Peele (both Second City alums), when a Chicago comic hits big, they take their pals along.

We asked Charna Halpern, artistic director of famed iO Theater to host a conversation among some of Chicago’s working comedians about what does make Chicago such a fertile breeding ground for funny. Below is an excerpt from that chat.

The group:

  • Charna Halpern, artistic director of iO Theater
  • Tim Ryder, ensemble of The Second city etc.
  • Jen Ellison, resident director at The Second City
  • Peter Kim, understudy at The Second City, and ensemble company at iO
  • Robin Hammond, director of marketing at The Second City
  • David Pasquesi, alumnus of The Second City, performer at iO and co-founder of The Mission Theater
  • TJ Jagadowski, alumnus of The Second City, performer at iO and co-founder of The Mission Theater

Charna Halpern: iO just completed this huge tour in Europe, and TJ and Dave just did some shows in Europe. It’s amazing to hear that Chicago is really a mecca.

David Pasquesi: Yeah, it was really interesting to be over in Europe… We were doing workshops with people from all over—in Western Europe and former Eastern Europe—and everyone was like, you guys do the Harold [longform improv], right? It’s kind of ubiquitous now, whereas not that long ago nobody knew what we were talking about.

Charna Halpern: There was a time when we had to stand outside with flyers and beg people to come in to see their team.

David Pasquesi: And they had no idea what they were watching.

Robin Hammond: We have three touring companies that go out all over the country, and it’s always interesting to meet people when they come to Chicago to study and they’re like, ‘I saw you at my university—this is why I came to Chicago.’ … I definitely think that Chicago has placed itself to be sort of at the center, where people know that they can come here. This is the birthplace of North American improv.

Charna Halpern: Improv in general. 

David Pasquesi: It used to be the only place, now there are other places, but this is kind of the mecca.

Charna Halpern: And I believe the reason for that is that in Chicago they really take the time to get good.

Robin Hammond: You have the opportunity to experiment, you have the opportunity to take risks.

Charna Halpern: I remember when Peter was a student; I remember when Jen was putting up her first show… and look at them now. They had time to grow and get good, where I find in L.A. a lot of times they come to iO [in Los Angeles] just because their manager said they should have it on their resume.

Jen Ellison: One of the great things about being in Chicago is that we have the stage time. I think it’s a little more difficult in more expensive cities—to be able to get a show together… It might be your friends, it might be your aunt three times in a row coming to see it, but you will be in front of people and get what is inside of your head outside of your head and see people respond to it so you can learn from it.

David Pasquesi: And I do believe that there’s something different about the mindset in Chicago... People are on stage to be on stage here; they’re not on stage to be plucked off to do something else—that’s not going to happen. It’s just not a possibility here. 

Tim Ryder: I’m sorry, it’s not!? [bangs his hand down on the table]

Charna Halpern: Funny, Tim.

Tim Ryder: No, I echo that completely, David. From what I hear from my friends who are in those other cities, improv out there is sort of like a means to an end… Not that people here in Chicago don’t have aspirations, but they’re also here because they want to do improv as an end.

Peter Kim: You can be an artist here or a content generator or whatever it is you’re doing and you won’t starve—the rent’s cheap enough.

Charna Halpern: When I first started in the ’80s…you had to go to nightclubs and beg people to let you play in front of the band equipment. Now there’s a million places in Chicago to go, so many places to get stage time.

Robin Hammond: And I think there’s a benefit to having a healthy community…. Being able to study at all those places and learn and find your voice and your artistic home.

David Pasquesi: The stuff we put up, we’re excited to show the other people.

TJ Jagadowski: I remember a friend put up this crummy little show a few years ago in New York and they had to pay, like $1,500 for a weekend for a tiny little room and no one’s coming and no one’s going to write about it. And here, you can find six people who are like, ‘You OK if we do it for free?’ And they’re like, ‘You’re OK if you do it for free?’ 

David Pasquesi: [When we started], there were, what, 12 people who knew what a Harold was? … And they were all attempting to do it.

Charna Halpern: And we’d be deciding whether or not we should still do a show because there were more of us on stage than there were in the audience.

Tim Ryder: Whether you’re on a stage with actual lights or in the back of a bar, that enthusiasm and attitude of ‘Let’s put on a show with you, my friends, my peers, my cast,’ is so infectious and so amazing that it just permeates the whole community.

David Pasquesi: I think one of the most important elements of why it’s supported in Chicago is the audience. They come to see stuff… and it’s not like race fans, they’re hoping to see a wreck. … They’re like, we’re going to get out of our house and maybe pay some money and give you a couple hours of our time, and this may blow, and we’re going to do it anyway, and we may do it again. The audiences in Chicago, I think, are the reason that allow everybody, you know, to attempt to fail.

Robin Hammond: I agree. I mean, really, 60614—our neighbors are the best…. They’re up for it, they’re game, they’re up to bring other people to see it and check it out.

Charna Halpern: Well, I really hope 60642 will come out. I’m really, really sure they’re just as good as 60614!

Tim Ryder: Zip code rivalries!

WHERE: Does anybody hope, aspire to be a celebrity comedian one day? Is Chicago the beginning for you or is this the end?

David Pasquesi: Being a ‘celebrity comedian’ just sounds like a terrible idea. I think when you put it that way, no one in public is going to admit that’s it.

TJ Jagadowski: The other choice, “Or is this the end?!”

WHERE: I meant, is this the top!?

Charna Halpern: Everyone wants to work and get more and more work and get better work and more fun work.

Jen Ellison: And if someone will pay you for that work, that’s awesome, but also, I think that it’s being in a position to create work, create interest, be able to express yourself, be able to commune with people who are exciting to work with, who are fun and interesting.

Tim Ryder: I like to make good things and be in good things and if somewhere along the way that turns out to being able to get a good table at a restaurant, that’s fine.

Peter Kim: Selfishly, I’d like to create something that endures. [I recently did a scene] that TJ had done, and it’s incredible to me to be able to sit in front of someone whose work I’m doing. I think that’s something I’d really like to aspire to, to leave something behind where it’s impactful enough for other people to view it again or remix it or whatever.

David Pasquesi: I remember walking into a show once and someone had taken a show we had written called “Farmin’” and they had reconfigured it to a banking concern, so they had changed it “Bankin.’”

Charna Halpern: and your souls…

David Pasquesi: …soared. So there’s that too. If it’s permanence we seek, improvisation is for sure the way to it!

WHERE: What happens when you’re up there and something just isn’t going to work? 

David Pasquesi: I don’t know what you mean.

Charna Halpern: Sometimes the best reactions are when things aren’t working.

Peter Kim: That’s the moment for me when I look at my partner, we’re in this together, let’s just keep going and…

Jen Ellison: …and I’m sorry…

Peter Kim: …and I’m so sorry, because it was probably my idea.

WHERE: Any particular moments you remember?

Tim Ryder: I don’t know if it’s me particularly…but sometimes I remember the bad times much more than the good, but those are the stories you tell each other in the van, those are your battle scars.

Jen Ellison: Very few great theater stories start or include the phrase, “and the audience sat quietly and listened.”

Charna Halpern: I remember we were hired by Abbot Labs to do a big show in a big auditorium and…they said they were going to do a little slideshow before they introduced us—the slideshow happened to be about a big employee there who just died…and they showed all these different pictures of people who were with her and said we’ll miss you forever, and now…iO! And we were like…really?

TJ Jagadowski: It’s really tough to learn from a scene that went well—you can’t always put your finger on why something worked or why people liked it… Any improviser worth their salt has done hundreds and hundreds of scenes that are terrible with the hope that you do fewer of them as you go.

David Pasquesi: Or fail more spectacularly next time. 

Tim Ryder: Do a few back flips as you fall.