Bill Murray. John Belushi. Tina Fey.
Del Close. Joan Rivers. Tim Meadows. Stephen Colbert. Steve Carell. Keegan-Michael Key. Seth Meyers. Amy Poehler. Jason Sudeikis. Bob Odenkirk. Cecily Strong.
Whether they were born and bred in the greater Chicago area, call the city their adoptive home, or simply spent a few years honing their craft in the Midwestern hub’s wealth of storied institutions, these folks are but the tip of the iceberg when it comes to the list of comedians who trace their careers back to the Windy City.
But despite the nods often paid to The Second City by its biggest-name exports, and the respect shown to iO and The Annoyance Theatre for their unique influences on the industry’s heavy-hitters, most of the aforementioned names are widely known not because of what they accomplished in Chicago but what they went on to do after their time here. That’s because nods and respect don’t pay the bills. Nevermind fame and fortune; a base-level career with a resumé boasting sketch-comedy experience and improv training can be hard to find in Chicago.
Yes, Chicago has a thriving theatre community. Technology has opened new doors of distribution for talented artists living all around the country. And NBC’s swath of “Chicago” shows—“Fire,” “PD,” et al.—has provided consistent television work beyond commercials. Also, plenty of stand-up comics have called Chicago their home, though that discipline warrants a story all its own.
But there are only so many cash-generating improv stages. Monetizing internet content is not an exact science, and, sooner or later, greater creative passions come calling.
Chicago is hallowed ground in the comedy industry, and rightfully so. It is the birthplace of long-form improvisation. The talent that flows from and through it is endless—but also boundless, often moving to entertainment hubs New York and Los Angeles. The roots of sketch and improv comedy are firmly planted in Chicago’s soil, and the trunk has grown mighty and strong over the years, but there is little room to branch out, to flourish, within city limits.
But it is Chicago’s far-reaching influence that might be what helps improv and sketch comedy not only survive but thrive for years to come.
For the past four years, Chris Witaske has lived in Los Angeles, performing regularly in the supporting role of Chris in the Netflix program “Love.” He also scored single-episode roles on the likes of “New Girl” and “The Comeback.” But not long before all of that, he was a child growing up in northwest-suburban St. Charles who got his start in the entertainment industry by performing as a birthday party magician.
It was a trip to The Second City at age thirteen that changed his course. “That’s when I knew that comedy was what I wanted to do,” he said. “That’s when I made the switch from magic to comedy, started taking improv classes at The Second City.”
Witaske said proximity to the center of the comedy world undoubtedly played a role in his future success. “When I started taking improv classes, I didn’t even have my driver’s license,” he said. “So, my dad would drive me into the city from the suburbs. It’s like an hour drive from St. Charles, but being close enough to where it was all happening really did make a big difference for me.”
By fifteen, Witaske knew comedy was something he wanted to pursue professionally, and he enveloped himself in Chicago’s comedy tapestry. When it came to film, Murray’s “Ghostbusters” and Belushi’s “Animal House” were on repeat, but he also started going to live shows regularly, and Chicago guys like T.J. Jagodowski (Sonic Drive-In commercials) stood out to him as some of the funniest in the business.
Witaske joined improv teams at iO and performed for original narrative shows at The Annoyance, trying to get a well-rounded education in sketch and improv. With the aim of getting hired by The Second City, he went to the University of Iowa to study theatre, auditioning for plays by Shakespeare and Chekhov but knowing his real passions were elsewhere. He said, “I knew, even when I was in college, that what I really wanted to do was sketch comedy.”
South of Chicago, Katie Rich was developing a love for comedy at Sandburg High School in Orland Park that would eventually lead to a stint on The Second City’s famed Mainstage and then a writing gig with “Saturday Night Live.” But it took her a bit longer to figure out what success in comedy could mean. “I remember in my high school, ‘What are you going to be?’” she recalled. “I remember saying I wanted to be an English teacher and then moonlight at The Second City, because I think I thought it was something you basically just did for your soul and fun. I didn’t realize that you could actually make a living off of it.”
“If you really, really want to be in a writers’ room for a sitcom, you kind of have to move to L.A. … You’re going to have to go where most of the work is.”
–Katie Rich, Orland Park native, Second City Alumna, “SNL” writer
Rich started attending Northwestern University, and during her sophomore year she took a fateful trip to iO, where she met co-founder Charna Halpern and landed an internship. But it was only when she eventually started touring with The Second City that she realized this could be more than something she did for fun on the side. “I was waiting tables and also touring, and I was able to stop waiting tables,” she said. “That’s when I was like, ‘Oh, maybe this is a thing.’”
Rich said iO and The Second City both prepared her for her future in different ways. At iO, she had a space to perform and experiment with her voice. “At Second City, I was actually finally able to make, you know, money off doing comedy,” she said.
Rich, too, said geographic convenience undoubtedly played a part in her success. “I always say I’m lucky to have been born in my home,” she said. “I know this is my home. I know this is where I want to be. So, I think I would have probably had to move here, and I didn’t have to do that. I didn’t have to deal with uprooting myself and getting acclimated to a new city. I just happened to be here.
“Then, I was exposed to Second City at such a young age. I think I was thirteen the first time I saw it. This was before YouTube and everything like that. Now, it doesn’t really matter where you are; you have access to so many things. But back then, proximity really did help.”
Despite their lifelong love for Chicago, both Rich and Witaske said they eventually had to consider opportunities elsewhere. Rich, who has maintained her local ties by living in Chicago while “SNL” is not in-season, said while it depends what one plans to do with comedy, professional options can be limited in her birthplace. For a writer or sketch performer, The Second City often is where the money starts and ends. “Unfortunately, that’s the top of the ladder here in Chicago, as far as sketch comedy goes,” Rich said. “It doesn’t pay well. The schedule is just not sustainable. … You don’t get any time off. Most shows close; the Mainstage show never closes.
“If you really, really want to be in a writers’ room for a sitcom, you kind of have to move to L.A. I’m not saying it won’t happen for you, necessarily—you can get opportunities in Chicago—but eventually you’re going to have to go to where most of the work is.”
Witaske pointed to Dave Pasquesi and Jagodowski as examples of finding success while staying in the Windy City. And he said there are opportunities in teaching improv, in addition to commercial work and select television shows. “I think nowadays you can stay and make it work,” he said. “For me, I think I always knew that I was going to go to one of the coasts, and it’s just because there’s more opportunity, I think. There are shows now shooting in Chicago. There’s just way more stuff being made in Los Angeles—and New York even.”
Witaske’s break came thanks to an agent and manager based in L.A. As Witaske was finishing a run with The Second City, he was convinced to head west. The move was “an adjustment,” he said, but it helped that Chicago is a community that travels well. “When people do move to L.A., I found that all the Chicago people really try to stick together,” Witaske said. “We all hang out all the time and go to each other’s birthday parties and collaborate on things. … Having come from Chicago, where a lot of my friends have moved out here, also, it really does help the transition, because L.A. is a big, weird place.”
Chicago’s three major improv comedy training grounds—The Second City, iO, and Annoyance—share a symbiotic relationship. While The Second City often acts as the standard-bearer of Chicago long-form improv comedy, it was at ImprovOlympic (now iO) where Halpern and the late Del Close pioneered the form and created the Harold structure—a three-scene performance, each scene using three distinct story arcs, with an intro and two interactive group activities—many still use today as a framework for their scenes. Meanwhile, Mick Napier’s Annoyance Theatre has been offering a different brand of absurdist humor plenty of big names have cited on their resumés since the late nineteen eighties. And Jennifer Estlin, who is Annoyance’s executive producer, said the theatre is set apart by original programming that is not only improv but also sketch, musical theatre, and solo shows.
“We tend to be able to be more experimental and, I guess, subversive in our content, because our customers, our patrons, are not as tourist-based as, for instance, Second City,” Estlin explained. “We really are a place where people can come and develop their voice, really learn what they have to say in the world of comedy.”
Matt Hovde serves as the artistic director of The Second City’s Training Center. He said the success alumni of the famed institution have found is connected by a simple philosophy the theatre tries to bestow upon its students. “That philosophy is built on things like valuing the ensemble, meaning the sum of the group is greater than the individual parts, that we collaborate here,” he said. “So, we really learn how to be supportive listeners and creative collaborators with our scene partners or sketch group. We learn how to connect to other people and unlock our best creative selves.”
Halpern said the Chicago scene is “complementary.” She does not see herself in competition with The Annoyance, and any competition that exists with The Second City is “a good competition.”
“It’s a drag to lose the talent, but it is also really helpful when people go on and they talk about their training here.”
– Jennifer Estlin, executive producer of Annoyance Theatre
Chicago comedy students have the opportunity to add three big names to their resumes, but more importantly Estlin said the pervading attitude encourages budding comedians to learn different aspects of the craft. And the theatres realize that is just as beneficial to them as their students. “People move fluidly between all the different theatres,” Estlin said. “We all help each other. Because we have different approaches, a student here is likely to be a student there and iO, as well.”
That has worked heavily in Chicago’s favor, making it a hub, or “Mecca,” in the world of sketch comedy. Estlin said people simply know it is the place to study improv under multiple disciplines and get exposure.
Halpern added, “When I started, those would be the days people would go to New York to be a star. Now, everyone comes to Chicago. This is Mecca. It’s the place to be.”
And much like a pilgrimage to the Holy Land, people who come away from the experience with greater understanding often spread the good word. “I think the comedy culture as a whole sees itself as one big family with these different branches,” Hovde said. “It’s pretty common for people who train here or teach here to move away and start a theatre in another town completely and be inspired by The Second City way. … There’s tons of stories like that. We feel really connected to the country, as a whole, as these offshoots of this art form.”
And that new growth undoubtedly brings nutrients back to Chicago. Hovde said what Second City sees today in terms of students is “many times over” what it was just twenty years ago. Adult programs that saw fewer than one thousand participants when Hovde was a student today see roughly three thousand at the Chicago facility alone. “The culture is thriving right now, socially, and with the other theatres in town, as well,” he said. “There’s never been a better time to come here and soak up comedy.”
Larrance Fingerhut and Jennifer Shepard studied and performed in Chicago for a decade before they decided it was time to open their own theatre. Fingerhut, a Maryland native and product of the New England Conservatory of Music, served as a music director for The Second City and iO. Shepard moved from Omaha to Iowa City when she attended the University of Iowa, and, like “most” of her theatre classmates, continued east to Chicago after graduation.
“I actually moved to Chicago with the intention of being a stage actress, but then I got invited to a show at ImprovOlympic within the first four months of my living there,” she said. “As soon as I saw that … I was really just drawn to it and immediately started taking classes.”
They had both worked in different capacities in improv before feeling like they hit a dead end. Around 2000, they started getting the idea for what four years later would become comedy club ImprovAcadia in Bar Harbor, Maine. “There was a point where I was looking around Chicago and I thought, ‘All right, I’m getting to an age, and if I’m not going to go for Second City, if I’m not going to try for that, then what am I going to do?’” Shepard said. “That’s when we came up with the idea of opening our own theatre.
“I guess it came from a point of, ‘How long can I perform for free at ImprovOlympic?’ Not forever. You’ve got to take those skills and apply them. If you don’t want to follow the paths available in Chicago, you’ve got to create your own. And I wasn’t the only person who left Chicago that year to open my own theatre.”
While Shepard hesitates to speak “authoritatively” on what is or is not possible for comedians in Chicago, she knew the city was not the place where she and Fingerhut were going to find lasting success. “My gut feeling, when we decided to do it, was that it was already pretty saturated, and I didn’t see where I would get enough capital for what you need to do it in Chicago,” she said, noting she has seen in Chicago a number of smaller theatres open and then close over the years, with few staying around for the long haul. “I think it’s very tough in Chicago. It’s super-competitive. There’s so much good improv there.”
She looked to places like Madison, Wisconsin, and Iowa City but did not think they had a large enough base of support for a theatre, but a trip to Bar Harbor solidified it as the place that could sustain ImprovAcadia and had a need for nighttime entertainment.
But starting in a new place was not easy. A lack of competition in Maine may have meant the marketplace was ripe for improv, but the audiences simply were not ready for it. Though the business is now fourteen years mature, its first three years were not easy. “It took some time,” Shepard said. “Our first season was hard, because nobody knew what improv was. It was kind of funny. You move from a place where everybody knows what it is, pretty much—if they love it or hate it, they know what it is. Out here, just blank stares. ‘What are you talking about?’”
The eventual success was thanks, in part, to a much-needed early assist from Chicago. While the rise of “Whose Line Is It Anyway” offered Shepard a frame of reference to offer her potential audiences, Chicago branching off dry land altogether set wind to the sails of ImprovAcadia in a way it never expected, and it has helped improv at large grow like a weed.
“Second City doing improv on Norwegian Cruise Lines exposed hundreds of thousands of people to improv,” Shepard said. “People would tell us, ‘Oh, the first time we saw it was on a ship. It made me want to come here.’ We get the reverse. People say, ‘I saw improv here, and then I went home and I started realizing there was improv around me.’ It’s totally shocking, because in Chicago, it’s like, ‘Oh, yeah, improv.’”
Witaske, meanwhile, had an awakening all his own, learning that all Chicago’s comedy traditions did not necessarily precede him when he got to Hollywood. “It depends on who you’re working with or who you’re auditioning for,” he said. “Some people really understand that Second City in Chicago is a big deal if you worked there, but other people, I found, don’t even know what it is.”
Rich said in New York, Chicago’s reputation is still important to a show like “SNL,” but it might not carry the same weight it used to, simply because great comedians are coming from all over the world at this point. And at the end of the day “funny is funny,” regardless of geography. “When you’re good, you’re good,” she said. “Everyone’s going to have a different style, but that doesn’t necessarily indicate what city they’re from. People are from so many places now. It’s not even just L.A. and New York and Chicago that shows hire from.”
But Witaske said he thinks people from Chicago still stand out, and it has a lot to do with the Midwest’s oft-touted work ethic. “People who come out of Chicago, I think, really respect comedy a lot, and, because they cut their teeth in a place where it is so important and such a big deal, I think you learn how to be not only a good comedian and improviser but you also learn how to be professional.”
Rich said the attitude is not exclusive to those with ties to Chicago, but she, too, has noticed that people from Chicago are able to roll with the punches of the entertainment industry. “They’re super-resilient,” she said. “I feel like they’re very willing to just try something once and see if it works. And I think they’re very, very collaborative.
“Chicago, in and of itself, is a collaborative place. … There is an idea of ensemble here in Chicago.”
For Shepard—though ImprovAcadia runs its own classes and she teaches beyond that at College of the Atlantic, and her style has adapted to a form that rests somewhere in between ComedySportz’s games and The Second City’s long-form work to cater to her audiences—the debt of gratitude she owes Chicago is not lost on her. She still considers the city’s training the best, and something that has inspired what she does halfway across the country. “What I base all my lesson plans off of, how I shape my classes, came directly from the experiences I had in Chicago,” she said. “Running the theatre has taught me a lot more about improv. In our season, I do something like two hundred and fifty shows in six months, which is a lot. … But I’m able to do all of that because of the training I received in Chicago.
“Chicago is still the epicenter of the modern, American improvisational and sketch comedy movement.”
For sketch and improv comedians who have honed their craft and are ready for the big time but reluctant to leave Chicago, there is hope. Those plentiful “Chicago” shows often hire Chicago actors. And their impact is not to be understated. “There are certainly people carving a career for themselves in Chicago, and there is a place for veteran actors here,” said Hovde, a product of the Chicago suburbs who started working with The Second City in 2003. “I used to say, ‘Oh, people come to Chicago to get good, and then they leave Chicago to get famous, right?’ That’s still true, because most of the major networks and national opportunities are still located in New York and L.A. For a lot of performers, they know when they come here that their time here might be limited to a few years. But there are more and more people that are finding ways to thrive in Chicago after those early years.”
Estlin, of The Annoyance, came to Chicago first to attend Northwestern University, left, and then came back again to pursue an acting career. She ended up creating a feature film with Napier, then heading film production for the The Annoyance before taking on her current role. In that time, she has watched Chicago grow to offer opportunities that were not nearly as plentiful when she started. “There’s so much more work, as far as the shows shooting in Chicago … and other things happening in that cinespace are allowing people to stay for longer and establish themselves and get some television under their belt,” she explained.
Coupling that with commercial work, opportunity exists. But, according to Halpern and Estlin, those things still often only delay the inevitable. “Ultimately, people still tend to go to one of the coasts,” Estlin said.
Halpern added, “If you get on ‘Saturday Night Live,’ you’ve got to go to New York. If you get heard by Seth Meyers or [Stephen] Colbert, you’ve got to go to New York. Get heard by Conan or any of these other [show hosts], you’ve got to go to L.A. It’s a sad fact.”
But while in some ways the departures signal a lack of opportunity at the top of the food chain in Chicago and the moves are inherently a net talent loss for the city, there also is an upside—one that has elevated Chicago to the upper echelon of comedy training. “It’s a drag to lose the talent, but it is also really helpful when people go on and they talk about their training here,” Estlin said. “And people are great about that. We do get a lot of recommendations.’”
To a guy like Witaske, that’s part of the arrangement: a comedy quid pro quo. “I think that Chicago means so much to me, and I try to give back as much as I can,” he said. “I think having gotten my training in Chicago and performed in Chicago, it’s definitely part of me, in my blood. I do wear it as a badge of pride. I certainly let people know that’s where I’m from.”
Shepard added of ImprovAcadia, “We definitely wear the moniker of Chicago improv proudly. It’s forward in our marketing. The Chicago name carries a lot of weight in comedy and with people and with improv. People who do know are always drawn by that Chicago brand.”
Hovde said a lot of The Second City’s growth can be attributed to that exact phenomenon, as people started tuning into Chicago around the same time they started tuning into “Saturday Night Live.” In the late seventies, when the first cast list for the show was released, people realized “about half” of the cast trained and performed at The Second City, Hovde said.
“People started to connect Chicago and Second City with the next up-and-coming generation of comedians,” Hovde said. “It did change our business forever, in a good way. I would say it still drives a lot of our theatre-going audiences and maybe some of our students, as well. They come here because they are admiring the careers some of these amazing comedians have gone on [to achieve].”
A big part of the draw for students of comedy to Chicago has a lot to do with that history. Halpern, a Chicago native, has been in the business for thirty-eight years. Whereas some schools of comedy around the United States are generations upon generations removed from the people who helped create them, Halpern is still overseeing the theatre. And she is not alone. “I have people who directly worked with Del and me for years and years,” she said. “I have teachers who have been here for fifteen years who are just fantastic at what they do.”
Halpern said Chicago’s place in the comedy scene remains unique because there is a delicate formula at play. It is a town that has a theatre community big enough to support the arts but small enough that people have the space to learn without so much pressure.
“We can take the time to get good,” she said. “There’s lots of space for everyone to get their sea legs. So, they get better and better and better.”
Hovde said when he studied comedy in Chicago in the late nineties, many people knew of “Saturday Night Live” and late-night talk shows, and maybe they saw opportunities in movies. But the landscape has changed drastically over the past ten years, and that is thanks, at least in part, to the influence Chicago’s comedy traditions have had on the nation. “People are coming in with a lot more sophistication about improvisation, partially because it’s being taught at the high school level and even earlier across the country now,” Hovde said. “They have access to many different outlets now for a career. People might still aspire to be on TV, or specifically ‘SNL,’ but there’s so much more self-generated content out there.”
And some simply are not in it for a career, according to Hovde. As college football is to the N.F.L., many see something unadulterated about Chicago’s scene by comparison to its coastal counterparts. “We still attract people who are passionate about this art form that aren’t always concerned about the consumer side of it,” he said. “To talk to the young, fresh college grads, the college students, or people that give up on their day jobs to come to Chicago to give comedy a try, there’s a pureness to the way we approach the art form here that I just don’t think is matched anywhere else.”
At the end of the day, Hovde agrees with Halpern that it is a climate that could not exist anywhere but Chicago. “We have pride, but we like to burst our own bubble sometimes,” he said. “That is a unique culture for why this works here. It kind of had to be here.
“L.A. has TV and film. Their processes reflect those studios and those processes there. In New York, obviously an amazing theatre town, but they are so much commercially driven, especially the Broadway model. … Chicago’s just a city that can support a smaller theatre scene. … We’re an accessible, intimate, underground theatre town, and that’s going to be a hotbed for different work than you’re going to find anywhere else.”
Halpern said there is something intangible about Chicago, too, that makes it special. As much as it is a place, it is also a state of mind. Like Rich, sketch and improv are simply where they belong in Chicago. No matter how far the branches spread, the traditions remain rooted here. And those who reach for new growth are still connected to the rings that mark the comedy form’s history and its future, as something alive.
“It’s just a feeling,” Halpern said. “You’re always here. You’re always home.”