Deconstructing Improv with Jeremy Sender

INJ 38 | Deconstructing Improv


Jeremy is a filmmaker and comedian. He was the creative director of The iO Comedy Network in Chicago. He has improvised on house teams at the UCB and iO Chicago. He and Lilliana Winkworth make up the sketch duo “Todd’s Friend Todd,” and his freelance clients include Nickelodeon, The Jim Henson Company, BuzzFeed, Cards Against Humanity, A&E, and the National Immigrant Justice Center.

Listen to Episode #38 here

Deconstructing Improv with Jeremy Sender

Our guest is Jeremy Sender. He is a filmmaker and comedian. He was the Creative Director of iO Comedy Network in Chicago. He has improvised on house teams at UCB and iO Chicago. He and Lilliana Winkworth make up the sketch duo, Todd’s Friend Todd. His freelance clients include Nickelodeon, The Jim Henson Company, BuzzFeed, Cards Against Humanity, A&E and The National Immigrant Justice Center. Welcome, Jeremy.

Thank you very much.

You’re here in Boulder driving to LA.

Yes. I left Chicago for good. I was there for three years and I lived in LA previously. I left with my hands held high and I said I’m never coming back. Three years later I’m going directly back.

This is the perfect question then. Supposed you’re headed to LA but I’m not going to allow you to work as a filmmaker or a comedian, what do you do?

I’m in LA and not able to follow any of my passions.

Maybe you have another passion outside of film and comedy.

I am fascinated by law. I don’t think I’d want to be a lawyer, but I feel like I would enjoy going to law school and learning about the Constitution. I had a handful of classes I took in college that weren’t about film or writing or something like that. I took a Civil Rights class and I took a Constitution class. I forget all of it, but I remember being very fascinated by it.

I’ll give you a tip. If you’re going to go to law school, then become a law professor.

I guess there are only two things you can do with a law degree, isn’t it?

Being a professor is hard, but it’s less hard than being a lawyer and you can use all your talents as a professor. I mean the teaching side of things.

I feel like being in a courtroom too. I would love to skip a bunch of steps of being a lawyer and just go into being a prosecutor and making grand statements to a jury. That would be fun, but that’s me wanting to be a ham a little bit.

Have you ever been on jury duty?

I haven’t. It’s very strange how I’ve never been called in for jury duty. It’s because I changed my residence every couple of years and they probably have trouble finding me.

I did a five-day jury a couple of summers ago. I didn’t want to do it but like most things in life, there were some benefits of it. The biggest benefit was it made me realized how happy I am that I don’t have a traditional 9 to 5 job. I don’t watch the clock since I had a regular 9 to 5 job. When I say watch the clock, I mean watch the clock tick down to some point in time because we would have a 10:00 break. We would have a noon lunch. We’d have a 3:00 break, then we’d finish. When lunch started and when the day ended was a little flexible based on the judge’s whims but more or less, those times were set. There were times when I was in that courtroom and I was looking at the clock going, “I can’t believe that 10:00 is taking so long to get here.” It was good also because you got a glimpse into the world. The civic duty, I think that stuff matters.

In the past years especially, I’m certainly in the boat of, “I need to contribute to society,” like activism and stuff like that. I feel like I might get a rush of the civic duty of it all. It depends. I’m sure 90% of cases for jury duty are super boring but it could be interesting to watch lawyers or judges or whoever just espouse their absolute expertise which I think is interesting.

I found the overall experience to be rather provocative and compelling. I took 57 pages of notes, but I’m an overachiever.

You’re an academic. No one else took notes at all.

We could submit questions and stuff, which I always did. I was like, “I’m going to make you regret taking me.”

Were there any criteria for questions or just whatever was on your mind?

INJ 38 | Deconstructing Improv
Deconstructing Improv: To be a good improviser, you have to be in the moment.


I don’t remember. They gave us some standards, but I don’t remember what they were. I wrote some pretty banging questions. I would say that from what I know of you, you’re a thoughtful guy. You’re what we call system-two guy. It’s interesting because as an improviser you end up being both of those things. I’ll do a very quick thing. Essentially, there are two modes of thought. These are along with some continuum but system-one is fast, it’s hot, it’s emotional, it’s intuitive, it’s your gut. When you represent system-one in a talk, I use Homer Simpson. Homer Simpson is a system-one. System-two is more controlled. It’s colder, it’s more calculated, it’s more brain. That’s like Spock, so it’s a Homer and Spock thing.

The idea is you need to be somewhat Homer to be a good improviser because you have to be in the moment and you have to be quick. On the other hand, you have to be like Spock especially long-form because you have to be thinking, you’re planning and listening, putting things, integrating. What I’m saying is you sitting on a jury, you seem like a little bit of a system-two guy. You’d be sitting there analyzing this stuff, you’re thinking it through. You’re doing extra work because you like to think. Homer doesn’t like to think, Spock likes to think.

You have done some UCBLA stuff. A few years ago when we met, you were talking about you’re in level 201.

I finished 201.

Have you done more since then?

No, not yet but I’m doing Sabbatical in LA. My plan is to do 301, 401, sketch class. What else should I do?

I never have taken the sketch writing classes there but only because I did all the improv classes through and then did advanced. I felt like I understood what they were going to teach me, which is very shortsighted but they have sketch classes at the Pack Theater now, which are taught by a lot of The Whitest Kids U’ Know guys. They had a TV show. They’re pretty popular sketch group called The Whitest Kids U’ Know.

I thought you’re making a joke because UCB is filled with some of the whitest kids you know.

That show is from the ‘90s. It was before calling their group that would have been a nail in the coffin.

I take that back. My 101 and 201 classes were surprisingly diverse.

They’re making a great effort to diversify because when I left, I was on a Mess Hall team which is one of the starter Harold team. All The Harold teams and most of the Mess Hall teams at that point were starting to make the effort at that point, but mostly white. Hopefully half and half, men and women but usually mostly men but it was moving in the right direction. I looked at the website to see what the teams look like since I’m going back out. It’s like night and day. It’s crazy. I realized how much more diverse it looked. I counted the number of white dudes per team and it’s usually much less than half. They’re making a concerted effort that seems to be going well.

There are a lot of reasons that’s leading in that direction. I did the intensive. These were two weeks, four days a week. I don’t know if there’s something about those intensive that lead to a different group of people.

People who have two weeks free and could spend $400. You get a certain type of privilege in there.

[bctt tweet=”When it’s done well, comedy seems like this beautiful erupting experience.” username=””]

You were clearly in that class. I know that if you’re awful in 101, it’s going to be very difficult but if you get a B, which I got in 101 and 201. Almost everyone gets B’s. We had some truly standout people. They were in the theater, they were actors. These were people pursuing their profession. They weren’t straight white dudes in my class. In one class I was the oldest person, in the other one I was the second oldest person. It’s a daytime class though. Maybe I was the second oldest in both classes.

The reason I brought it up is that your system-one, system-two sounds a lot like what Billy Merritt talks about which is you’re a pirate, improviser or a robot and a ninja. He has those three types. Pirate is like Homer Simpson, very system-one. Totally feeling and just instinctual. Then robot is the Spock. They’re thinky, they’re on the back line and they’re coming up with moves for two scenes from now and the like. Ninja is not the in-between but is the type of player who can be on the back line watching a scene, recognizing what’s wrong. Coming in and saying one thing, leaving and fixing the entire thing.

INJ 38 | Deconstructing Improv
Thinking, Fast and Slow

If you want to read about this, my postdoc adviser, Daniel Kahneman, won the Nobel Prize in Economics for Psychological Insights into Economics. He wrote a book called Thinking, Fast and Slow, fast system-one, slow system-two. Billy Merritt’s book would be improvising as a pirate, robot or maybe a ninja or something like that. You’re moving back to LA, tell me why.

I did three years in Chicago and I loved it and for a lot of reasons. My girlfriend went there for a job and we were both living in LA previously. We were both pretty frustrated with our lot there. We have moved there. We did our last semester of college there. We did an internship and then we stayed. We were very young in LA with absolutely zero professional experience and so it’s hard.

I love LA. I spent a lot of time there. What makes LA better is having money.

We were living in Valley Village in one room in a three-bedroom apartment that we subleted. It was the worst. The only thing around us was a 7-Eleven. It was hot and it was a valley. Then we visited a handful of times since then and we’re staying in Pasadena and going around Echo Park and hanging out in the hills. When you are rich here, this is great.

I hope you make boatloads of cash in Chicago.

I don’t know if this is because we are in Chicago or because we have more distance between us in college, but we have both figured out our paths a little bit clearer and I certainly got a lot of good experience in Chicago. Most of the freelance work that you read there was from me being out there which is so strange because they’re all companies based in New York and LA, but I was in Chicago working for a lot of them. Chicago is a great town to take a lot of risks and make a lot of mistakes with very low stakes. When people come to town from New York or LA or bigger industry towns, they romanticize Chicago and think like, “This guy’s writing this web series from Chicago, we have to bring him out to LA,” which is stupid because I could write the exact same bad web series in LA or in Kansas. Chicago is a great middle ground where people will see you and if you’re making crap it might be a little romanticized and even if it’s not romanticized the palette refreshes a lot more often.

For the Humor Code launch, the Humor Research Lab, my co-author, Joel Warner, and I created the list of the list of The Funniest Cities in America. We had an algorithm called the Humor Algorithm. HA calculated and ranked the funniest cities in America. Chicago was number one.

When did you do that?


That’s probably accurate. My experience in LA when I went there first, the improv I see there, no disrespect to Chicago but the improv I saw in LA is, on the whole, better than the improv I see in Chicago but because it’s people from Chicago and New York and other cities who got good and are in LA. It’s like the graduate school of improv. Chicago has plenty of industry but that is a huge industry of the city. People come out here from anywhere to do comedy specifically and that reach there for sure.

What I liked about Chicago being number one, LA and New York were six and seven or seven and six, is oftentimes when people find out we did this Funny Cities list, I say “What do you think is the funniest city in America?” The most common response is Chicago. I like that it came out first and that when people guess they guess Chicago.

That’s a great confirmation.

You were the Creative Director for iO Comedy Network in Chicago and you did that these past few years and then you did freelance work.

I did it for a little over a year.

Then you did freelance work?


Tell me what were those jobs like?

The iO Comedy Network is the video arm of the iO Theater. iO Theater is like the theater that Del Close try to help and open. It’s the birthplace of long-form improv. Do you know the story of it at all?

I know some of it, but I have listeners now. This is great because I’ve talked to improvisers before, not many but I have. Can you pretend I don’t know anything about the history of improv? Can you give me a quick rundown?

I’ll give an abridged version. The Second City is the birthplace of sketch comedy theater that uses improv.

What’s the difference between a sketch comedy and improv?

Sketch comedy is pre-written comedy scenes and improv is short for improvisation. No pre-planning or no writing. You might have rules to a game that you’re going to play or something like that, but the specifics are totally made spontaneously on the spot.

Saturday Night Live is a sketch comedy. Whose Line Is It Anyway? is improv comedy.

They know what game they’re playing but the specifics are totally made up. The Second City Theater in Chicago was the birthplace of popularized sketch comedy. They used improv comedy as a tool to rehearse and come up with ideas for sketches and write sketches out. The main show at Second City, they have something called Process, which is two months or so handful of weeks where they improvise in front of audiences. They’re writing independently a lot as well and they use those ideas to hone in a review or a sketch show. That was the mode of comedy or that type of comedy for a long time. Improv was seen as this rehearsal tool for coming up with ideas. Del Close was a guy from San Francisco. I know that a lot of The Second City folks came from doing this type of thing in San Francisco and brought it to Chicago. Del Close was a director at The Second City. He was helping comedians improvise and come up with sketch ideas. At a certain point, he was like, “The improv is getting good. We are hitting a tipping point where we can turn the improv into the show.” It’s an art form that can stand alone. He hit a lot of naysayers. A lot of people vehemently disagreed with him and he was famously cantankerous and grump. De did a lot of drugs and he considered himself a witch. He was a weird dude.

He sounds like the perfect person to innovate.

He died pretty young because he was doing a ton of drugs all the time. He refused to live by anybody else’s standards for sure.

The reason the average person gets into comedy is that either they don’t play well with others in the traditional sense. Like a classroom is a little too confining and too rules-oriented. That 9 to 5, the rat race and so on. The other one is they’re impish. They don’t like being told what to do. It’s not only just the lifestyle. They like to keep their own hours and do whatever. They also don’t like to be told how they need to behave, which helps make good comedy clearly because comedy plays on misbehavior. At the very least, it plays on seeing the world in a different way. Yet here you are in this world of comedy filled with these imps, filled with these people who like to do it their own way. Then here comes this guy who’s going, “This improv thing has legs. We could do improv shows.” Then there’s this thing called the status quo bias, which is we tend to think whatever is in place is the right thing. The deviations from it, while they may be beneficial, people tend to focus on the cost. Even this group of people go, “No. The sketch thing, that’s where it’s at.”

All things considered, The Second City started in the late ‘50s or early ‘60s and this was happening in the late ‘70s or early ‘80s. It’s been there for a while but all things considered, it’s still pretty new. These are all the founders. It’s not like it had been passed down from generations or anything. You’re right, all of a sudden they’re like, “No, we deviated and now we’re right.”

Does that explain a little bit about why there are these different brands of improv?

INJ 38 | Deconstructing Improv
Truth in Comedy: The Manual for Improvisation

I think so, but it’s a little more nuance. Del Close thinks improv can be the thing. He teams up with Charna Halpern who still runs the iO Theater. If I am remembering the back of the book, Truth in Comedy, the ImprovOlympic Theater already existed. I don’t think they founded it, but they took it over. It’s a good book. If you take a class at the iO Theater in Chicago, you’ll get one for free so don’t buy one. They take over the ImprovOlympic Theater and they created this improv form called The Harold. As opposed to a type of improv game you might see in Whose Lines Is It Anyway? where it’s like, “This person has a secret and it’s blank,” and then they play out like a two-minute scene. The Harold is this long form where you get a single suggestion and then the cast improvises for 20 to 30 minutes and it’s the whole show. That went through a whole bunch of different iterations and slowly they started teaching classes and by the late ‘80s, it was a pretty sustainable art form. Then you had this in the ‘90s and early 2000s. It’s just every person that you see on TV or SNL or whatever, many of the people you see got their start from long-form improv.

I know there was this very clear switch in television away from stand-up comics to improvisers. It all makes sense. Stand-up comics are good joke writers. They are performers, but improvisers are more naturally actors. You can also bring that skill to a taping where they can try things, you can use improv. Judd Apatow does this on a regular basis with his films where he has the actors do the line that is written on the script and then do 30 more improvisational takes.

They cut a second version of Anchorman based off of the takes they didn’t use in a different movie.

[bctt tweet=”What is funny is this unusual thing that has some justification.” username=””]

The other thing that is interesting about improv that I don’t think the average person gets is the notion of rules. There’s a set of rules associated especially with The Harold. The way I like to think about it and talk about it because a lot of people know sports well. In some ways, it’s like a sport except that there’s no competition. It’s a collaborative game. There are rules associated with basketball when the game starts and when the game ends and what happens and so on.

Have you heard Keegan-Michael Key talks about that and he relates it to basketball? He said that Dr. Naismith drew out the rules like these lines are out of bounds, the hoop is this high, you can dribble this many times or you take this many steps but within those rules, you can do whatever you want. That’s how you get Michael Jordan or LeBron James who are innovators in the game. That’s why watching basketball is not boring for people because you have this set of guidelines but then it’s pushing those boundaries.

There are lots of uncertainty and some games are good and some games are less good. They teach The Harold. When you go to the average improv show, you’re seeing some version of The Harold. Jane Saltzman was here. This is a short form which is more of game-based, short, few minute things that are very jokey.

The premise of what’s about to happen is explicitly laid out to the audience and then they do that game. Like in Whose Line there are newscasters. There are still a handful like ComedySportz is a big theater that still does that. That’s a very accessible improv comedy.

I love it. I admit it. It’s so funny.

It would be disingenuous for people to pretend like they full hate it. A lot of long-form improvisers are like, “I don’t feel the need to do it.”

It’s like going to a dunk contest. It’s great. Who doesn’t like a good dunk contest? I understand the artist wants The Harold.

It’s much more fulfilling that way I think.

We don’t have time to go into this but the thing about The Harold is it’s incredibly complicated. When it’s done well it seems like this beautiful erupting experience where things are getting pulled out of the air and so on. If you know The Harold or the beats of The Harold, there’s a structure on it that on one hand it makes it seem less magical but on the other hand, it makes it seem more magical. You could probably explain The Harold better, but the idea is there are these beats. What happens is as you go on in the show you have to revisit topics in new ways and then at the very end, you have to integrate all the topics that have been covered. That is an incredibly difficult skill.

It’s like you’re hitting your head and rubbing your belly all at the same time. It’s from column A and column B all at once. It’s super difficult.

The closest thing that I get to that besides when I try doing the baby steps at this point, I’ve never done a full Harold obviously, is this podcast. This podcast is an improvisational experience. I have some rules. I have some guidelines but I’m already thinking we have to get back to what you do as a creative director. We have to get back to what you were doing with BuzzFeed and A&E. We still have to get back to why you’re going back to Los Angeles. In the back of my mind, it’s an amazing skill that I’m still working on but it’s a different one than when I’m on the other side of the mic when I’m getting asked questions. I’m not saying that this podcast is as hard as The Harold, but it has some of those same elements. How do we get iO? How do we get UCB? How do we get Second City? How do we get ComedySportz? Those are the major brands.

I think so. There are a handful of others like The Groundlings and stuff. There’s The Second City and then the ImprovOlympic Theater branches off from that. I should clarify, it’s called The ImprovOlympic Theater and then at a certain point the actual Olympics, the Olympic Committee realized that the ImprovOlympic Theater was a thing and sued them. It might have become a real lawsuit. For some reason, these people who administrate athleticism think that people are going to go to Chicago and see a comedy show and be like, “The Olympics were really terrible.” They thought that. The theater changed their name to iO as the initials. It’s the iO Theater now. iO starts getting popular. Chris Farley comes out of there, Mike Myers, Tina Fey, Amy Poehler, a whole host of famous comedians and a group that is there is the Upright Citizens Brigade.

Were they house team called Upright Citizens Brigade?

I don’t think they were like a Harold team at the theater, but they were performing sketch and improv at the theater. They were teachers there and regular performers there and that was their independent thing. That included Amy Poehler, Matt Besser, Matt Walsh, Ian Roberts and when they are in Chicago a bunch of other people as well, Frasier Sands and Neil Flynn and a bunch of well-known comedians now. Those first four I mentioned at a certain point decided like, “We’ve been in Chicago doing this for a long time and we’re hitting momentum that we can capitalize on,” so they move to New York. They had a show on Comedy Central called the Upright Citizens Brigade. That was a sketch show and while they’re out there they start teaching improv because long-form improv doesn’t exist in New York in the late ‘90s. They start teaching classes and it blows that scene up. They’re the most popular comedy game in town and they open a theater and they open a second theater in New York and then they open a theater in LA and now a second theater in LA. It just grew.

Not surprisingly in hindsight. They’re the best. Improv is fun. It’s an important skill to have if you want to be in entertainment. It’s an important skill to have in life. Then you move it to the two biggest cities in the United States that also happened to be the two primary hubs of entertainment.

It begs the question of why iO was just in Chicago for all this time?

You talk about the status quo bias. Some of it is unique to have a business mind and artists don’t always have business minds.

Second City historically has been a bunch of others. There is a Second City in Hollywood. I don’t know when they opened but it’s a small operation. They still exist in Toronto. They had one in Detroit that was popular. They had one in Vegas that was popular. I think right now it’s Hollywood, Chicago and Toronto but they’ve been all over. I also had a theater in LA that closed unceremoniously.

INJ 38 | Deconstructing Improv
Deconstructing Improv: Artists don’t always have business minds.


In your bio you sent me, you say that you use the Benign Violation Theory in sketch writing classes. You taught it at iO Chicago. You said you love it and you use it. This is not why you’re on. You would be on even if you didn’t. There are some subtle differences between these brands of improv. Correct me if I’m wrong, UCB is much more about pursuing laughs than iO and you like laughs. Tell me how you’re using the Benign Violation Theory.

I wrote the first draft of an essay that maybe will be published in a not real publication but like a Chicago improv journal about the difference between improv comedy and improv theater. Chicago’s all about improv theater. That’s where improv started. It has that groundwork to it. They have piano accompanying and they have table service. It feels more like a night out theater and in UCB you’re cramped around the stage, $5. It feels more like comedy and in style too. The way I think about it is that improv theater invests a lot in that benign and that based reality of the theater, the relationship, the themes, the stakes, the drama of it all.

Once that is set in stone in three dimensional, then you can pepper in little comedic bits. Those hit harder because you’ve created this deep three-dimensional world. UCB is the inverse. You have to lay the groundwork in a base reality in order to figure out what your jokes are going to be about. It’s geared towards finding that singular comedic premise, that unusual thing and then justifying that. Making a pattern out of that and taking that singular comedic idea and milking as much as you can. It’s like very economical scenes and you’re right. It’s the same concept but approached in a more theatrical way where you may be able to watch a scene that wasn’t very funny. There may be a couple of moments of levity but it is good theater.

Most things we watch on TV or in film aren’t comedic and yet they are compelling and entertaining emotional. The good evidence for this is in UCB. If you take 101, it’s basically giving you all the basics of how to create a scene. 201 teaches you what they call game which is finding the unusual thing that can be justified. What was funny is when I took 201, I finally figured out why improv was funny. It was one of the things that I was like, “This doesn’t lend itself to the Benign Violation Theory as nicely as other forms of comedy do.”

It does much more.

Maybe you probably do because you live in the world of improv but as someone who watches improv, it’s not obvious. I had to start doing it to figure it out. I want to hear how you talk about this, but my vernacular is the thing that’s funny is this unusual thing that has some justification. This thing that’s a violation that’s benign, this behavior that’s wrong is okay from this other perspective. They don’t use my language in it but that’s what I think is happening.

They don’t use the language but they’re synonyms totally. Justifying unusual thing is making a violation benign, almost precisely. The way I talk about it in my classes, I will have students come in with a general premise for a sketch they want to write. We talk about what they like about it. What they think is funny about it. A lot of times that takes a fair amount of digging but eventually what you get to is an idea that is unusual based in a context. There’s a contrast to the thing that they like versus the setting that it’s in. I will write those two down in a whiteboard. The benign, the setting, the base reality and the violation, the unusual thing. We’ll talk about what about that unusual thing they like and we’ll use that to just create a bunch more steps in that pattern. Likewise, we’ll go to that benign element and create a lot more steps in that pattern. There was a scene about a boy bringing a girlfriend home to meet his parents and the joke was that the parents say, “Make yourself at home” and she’s way over does it. She starts raiding the fridge and baking cookies and just burping and stuff like that. Not an amazing premise but there’s comedy for sure.

The place to look for these is Saturday Night Live skits. Especially some of the classic ones like Bill Murray, lounge singer but a weirdo.

That’s the simplest version of it. It’s like a lounge singer, we have all these ideas of what a lounge singer does and then he does weird things like the weird version of it.

I went down the YouTube rabbit hole at one point. They’ve done two of these with alien abduction with Ryan Gosling as the guest host. Kate McKinnon is in it. It’s interesting because the base-reality doesn’t have to be normal. It just has to be normal within that reality. These three people they’ve all been abducted by aliens. This is to the audience. If you have not seen this sketch, do yourself a favor and watch both of the sketches because it’s gold. Two of the abductees have these magical wonderful experiences and the third, Kate McKinnon, gets molested but what’s interesting about it is she’s not really upset about it. How do we make the violation benign is she has a line in there where she goes, “I’ll tell you, it wasn’t my worst Saturday night.”

Because she’s okay with it. That’s how I like to look at scenes and I’m getting better improvising and using this tool in my brain in the present a little bit better. I look at it as like a bubble level type of thing. You lean too far to one side is too violating, too far the other side is too benign. You’ve got to balance in between. In that scene, the context of the base reality is that these people were abducted by aliens and these people had magical surreal experiences, which in the world is super violating because it’s not real. We’ve seen sci-fi stuff and it’s presented as the context. We’ve zeroed the scale there. When Kate McKinnon is talking about how she was probed and molested, that’s a violation based against that context but it’s also gross and sad. I would argue that then the bubble level is leaning too far to the left and is getting too violating. We need to hit that benign more so what makes it more even is her being both molested in a terrible situation but also being, “It’s not so bad.”

What is interesting is you’re approaching it from taking this theory and then moving it down into practice. I get the sense that a lot of comedians have good instincts. In the same way that you don’t need to know physics to hit a baseball over the fence but the better you understand the movement of the ball, then the better you can hit it. It can help but it is by no means sufficient or necessary.

Everybody needs a different skill set or everyone has a different skill set and needs different information. They’re probably baseball players who have the muscle memory and if they thought about it would instantly suck at it and then there are people who know like, “If I hit a ball that’s a little more outside, I’ll get more leverage.”

Ted Williams famously wrote a book about hitting a baseball. There were a hundred places in the strike zone that he illustrates in the book. He’s like you, you’re like the Ted Williams of improv. You find it more useful for a sketch because you can be more system-two.

When people think about sketch, they expect to see polished stuff. You can think about it on improv but it’s most helpful when you can sit down with an idea that you might be able to improvise but then think about the theory behind it and punch it up to eleven.

[bctt tweet=”Everyone has a different skill set and needs different information.” username=””]

I’m excited to take a sketch class because that probably works a little better for me in terms of the skills that I already have. Also, it allows me to be slow. Creative director, what are you doing at iO Chicago?

I left but I was overseeing the video side of iO. The work existed before I took over. They do have a YouTube and a Facebook channel. The Facebook channel is much more popular. If you search on Facebook for iO Comedy Network, you’ll find a bunch of videos. When I took over, I implemented network teams, which mirror Harold teams at the theater. These are video sketch teams and they’re made of writers and actors and directors and they work together to make video sketches. I was overseeing that, giving script notes, helping out with production and post and release. That was the bulk of it. I was the executive producer of iO’s sketch videos. In the short of it, that’s what I was doing. I designed that structure.

INJ 38 | Deconstructing Improv
Deconstructing Improv: The base-reality doesn’t have to be normal. It just has to be normal within that reality.


Then on the side, you were doing some freelance work. Were you making comedy for these?

For some, I worked with BuzzFeed and Cards Against Humanity. For BuzzFeed, we did branded content stuff. It’s like the BuzzFeed listicle video but then at the end it’s like, “Brought to you by Jewel-Osco,” which is the big grocery store out in Chicago. That’s a little more structured.

Do you like that work?

I do like it. I love BuzzFeed, but they have a very specific style and voice. It’s much less getting my ideas in and fitting into that.

I assume you get a creative brief of some sort?

Yes, for sure. I was brought on as a producer for it because they were shooting this in Chicago. They had the script written but I had a lot of arguably creative duties. I wasn’t going to change the content. With other clients, for instance it was a small client but there is a gym in Chicago that we made a digital commercial for. They wanted to do essentially a sketch and they wrote this idea out. We had to keep it to their idea, but we could pitch jokes and shoot it in the style that we wanted to. There’s a lot of overlap.

Back to the teaching thing, you taught sketches.

I taught sketch at iO while I was there. That was like video sketch, part of it was also learning screenwriting format and stuff like that.

My sense is that a lot of these improv sketch brands is a way to get people paid. You have these people and these house teams are very good, but they don’t get paid that much for performing. They teach classes and they make a little bit of money.

Yes, and also from the students’ perspective too it’s that opportunity to translate that nebulous stuff they do on stage and have a physical product and show it to people and potentially leverage that into acting and writing. Otherwise, you get stuck doing improv on stage. The only people who see it are the twenty or so people in the room and most of those people are not going to help you out.

I’m thrilled that you found some use in the theory.

I’ve gotten a lot of good feedback from people. It’s very similar to UCB theory, just using different terms but everybody who has taken the class that I taught gave me feedback of like, “I didn’t understand why things work and now I do.

When I took these improv classes, I don’t tell people that I study comedy. It would be distracting. I just say I’m a professor. It’s in LA, so all they care about is themselves. They don’t ask any other questions so it’s safe. The first day of 201, this guy comes in. He didn’t end up becoming our instructor. He says, “As an aside, it’s probably useful for me to explain what makes things funny.” I’m just sitting there going, “This got to be good.” He does this whole spiel about what makes things funny and I’m thinking, I’m going, “No, that’s not it.” I almost sent him my book and then I was like, “Forget it. I wouldn’t worry about it.” You are in Boulder visiting friends on your way back to Los Angeles. What is it?

There’s no one specific thing. I got this job and I’m doing this. In my time in Chicago especially with Lilliana, my sketch partner, we’ve been working a lot of stuff and we’ve opened doors with some production companies and networks and people so that by no means are we hitting it big or making it.

You want to go to a bigger stage.

I was ready to leave the Comedy Network. I felt like I had done my duties and it feels like the time to move on from the medium stage to attempt the big stage. We got to this point where we would like to write a new thing or make a new sketch and send it out to people in New York but mostly LA. She’s not moving out quite yet but she’s from there so she’s going to. It just feels the time to be out there and be like, “I made this thing. Do you want to get lunch?” which makes more sense for us.

What would be the ideal outcome?

We would love to sell a TV show. In the more immediate sense, we would love to write for TV.

Jeremy, you’re a smart man. I say this and I’ve said this before, a comedy writing job in Los Angeles is one of the best jobs in entertainment. I’ll tell you why. The money is pretty good. The hours are long, but the work is regular. It’s real creative work. You laugh a lot. It’s hard but everything is worth doing. You’re surrounded by these smart creative funny people. You’re creating smart hopefully at least funny content. You’re getting a regular paycheck. You’re under the radar so you can live a normal life.

The idea of being famous sounds terrifying to me. If I can be one of those moles in a sweatshirt writing the words that would be super cool.

Especially within comedy. There may be better jobs in entertainment but as far as jobs in comedy, it can be a good life if you can pull it off, if you can do it.

That’s the last affirmation I needed. I’m going to go do it.

I hope it works out for you and I’m sure I’ll see you when I’m in LA again. Final question, what are you reading, watching or listening to that really stands out?

I got back into Better Call Saul. That’s what I’m bingeing right now. For some reason, Better Call Saul is renowned for being one of the best shows that was ever on television and people aren’t watching Better Call Saul that much. It’s only fell out of my brain for a long time and I got back into it. It has a slow start but when I got into it, I realized it’s back to my weird affinity towards legal stuff. It’s a really well-done legal drama that feels like it has the same stakes. I get the same adrenaline rush from Better Call Saul as I did from Breaking Bad.

I’ve not watched it. Is it comedic at all?

A little bit. Breaking Bad was also comedic a little bit. This is much gory for sure and it’s a little wonkier. There’s a lot of courtroom drama.

Anything else besides Better Call Saul that you’re watching? Anything you’re reading or listening to?

I started the Fifth Season by N. K. Jemisin, which is a sci-fi book and it’s a trilogy. I started it, but it came recommended from a couple of friends and so far it’s already fascinating. It’s like uninhabitable Earth. It was like you have to figure out modes to survive from what I understand so far. The reason I would recommend it is the story behind it is fascinating.

It sounds like a movie. There has to be a movie coming.

It must be, but I don’t think that was the intention because the author is this black woman. She’s an amazing writer but she has a hard time publishing this book and so she Kickstarted it. She wrote three of them on that funding and they are all bestsellers now. I recommend it.

Jeremy, thank you for taking some time out of your little vacation, your trip, to meet with me.

Thank you for meeting with me.

Resources mentioned:

 About Jeremy Sender

INJ 38 | Deconstructing ImprovJeremy is a filmmaker and comedian. He was the creative director of The iO Comedy Network in Chicago. He has improvised on house teams at the UCB and iO Chicago. He and Lilliana Winkworth make up the sketch duo “Todd’s Friend Todd,” And his freelance clients include Nickelodeon, The Jim Henson Company, BuzzFeed, Cards Against Humanity, A&E, and the National Immigrant Justice Center.

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