Be prepared to work really hard.


Greg Hess is a man of many comedic talents. He is the only member of both my favorite improv troupes, Cook County Social Club and The Improvised Shakespeare Company, and he is also now representing the Chicago comedy community in Los Angeles with the production of his new pilot “Schlub Life.” I was able to catch up with Greg the day after his last Tuesday night run of Cook County and we chatted about shooting this pilot, the beginnings and the closing night of Cook County and what it’s like to work in this industry with your significant other.

You are the only member of both of my favorite improv troupes, Cook County and Improvised Shakespeare, so this is like a two-for-one deal for me. Also congratulations on the pilot, which we’ll get into in a few minutes. 

But let’s start at the root of this comedy career path, where did this all begin?
I did some theatre as a kid, just community theatre. But it mostly started just hanging out around the dinner table which was me, my mom, dad and younger brother and sister. I was always kind of a “cut-up” if you will. I didn’t grow up with television, because we lived in a really rural area, so we never had cable or satellite. We had a TV and a VCR so while most people were watching SNL as kids and first finding out about popular culture through television, I was watching Monty Python, The Dick Van Dyke Show, the Marx Brothers, Laurel and Hardy and Danny Kay. As a kid, I thought Danny Kay was a contemporary comedian who was working at the time. Growing up he was probably my greatest comedic influence until I was about 13. Then I made friends who had TV where I could go watch SNL. So I grew up watching really old comedy. I would memorize old routines and I’d put them up for the family.

Did your brother and sister join in on the fun?
Ha, no. We’re all very different. They’re not exactly performance driven. It was always just me trying to make my whole family laugh. Both of my parents are really funny. In another dimension, I think my mom is probably an actor. Both of them have great senses of humor.

So were they supportive in you making this career choice?
Yeah, they’ve always been really supportive. I think the hard thing about improv, in general, is that it’s a hard career to explain.

So when did you start doing improv?
I started doing improv in college (at the College of William & Mary). I saw it for the first time when I was on a freshman visit and it totally blew my mind. That’s pretty much why I went there.

So you studied theatre?
No, I studied religion.

You studied religion?
Yeah, haha.

Yeah, I was a Religious Studies major.

Was that part of your upbringing?
It was. I grew up Presbyterian, a very involved Presbyterian. I consider myself sort of ethnically Presbyterian. I was in youth group and worked in summer camps and all that stuff. I had an interest in religion, but I’d say the focus of my major was more American religious history. I majored in it just because those were the classes I enjoyed the most. I did plays in college but improv was my focus, with a minor in religion. That’s what I always like to say.

Nice. So did you move to Chicago right after college?
Sort of. I spend the summer after I graduated in Northern Ireland.

What, that’s amazing!
Haha, yeah. I worked in Northern Ireland during college, because I originally thought I was going to go into peace and conflict resolution.

Wow, you’re all over the place.
Yeah, but when it came to religious conflict resolution, Northern Ireland is an interesting place to study. During college I worked in a reconciliation center learning about how they did cross border conflict resolution. After college I went back with a group of about ten high school students that I basically had for the entire summer in Northern Ireland and I was the liaison for everyone.

Are you Irish?
No, I just always liked it there. I like Irish people.

Me too. I have a lot of close Irish friends.
Actually, it was while I was there, I had the thought that I should move to Chicago. I originally thought I was going to go to graduate school right away. But my college roommate, Martin Wilson from Improvised Shakespeare, had moved here and we knew a bunch of people from college that were already here. So I told myself I’d give it a year and see what it’s like and here we are, 10 years later in a Starbucks.

There we go. Ok, so when you decided to move here, what was your plan?
I think the cool thing about Chicago is that you get bitten by the bug pretty early. I saw so many amazing shows and I came up with a really strong generation of improvisers, which was really exciting too. By about level 3 at iO, we were doing comedy about every night of the week, trying to make it here. By “make it,” I just mean to play as much as possible and be on teams and such. In classes, I met all the guys on Cook County Social Club. I actually had met Bill [Cochran] and Mark [Raterman] during college at the first Dirty South Improv Festival. So as soon as I moved to Chicago, I knew I had to be friends with them. We had a really strong and committed class of people that were moving through iO and Second City, so it all kind of happened right away. I just wanted to be performing a lot. A few years later, I started performing with Baby Wants Candy, which was really huge for me. That was the group that I was amazed by when I first moved to Chicago.

Baby Wants Candy is incredible.
They’re amazing. At the time, some of the original members were still playing and they were still at iO. Aside from my Harold team, I was playing with Baby and it was such an honor to join that group.

So how did you pay bills?
I worked a bunch of day jobs so I could do comedy at night.

Where did you work?
I worked a lot of temp jobs. I worked at The University of Chicago and at an ad agency and then I got a permanent job at the Art Institute as an assistant in the European painting department. I loved working there; it was a really great job. Then I moved up to development and grant writing and I was on the team that helped build the modern wing.

Nice work.
I left just as the modern wing started to go up in 2006.

Ok, so you’re working day jobs to do comedy at night. That seems to be a common thread.
Absolutely. At the time, a lot of the guys I was playing with were all working at a law office down the street. Bill Cochran, Mark Raterman, TJ Miller, Nick Vatterott, Micah Sherman and Morte Burke, all these guys who are still in comedy worked at this same law firm. So we’d all meet for lunch pretty frequently. Oh and Brendan Jennings was working there too.

Wait, what? Haha, Brendan Jennings at a law firm?GregHess_CookCountyQuote
He can type like 13 words a minute. They were always hungover and helping Brendan because he couldn’t finish his work on time.

Haha. 13 words a minute. Perfect.
I think one day we had 180 emails that we sent back and forth to each other. Basically, we were all slacking off, sending email bits to each other and meeting for lunch and that’s pretty much how Cook County Social Club started.

Ok so it started with this group of buddies who just met for lunch all the time and you all found each other funny, so you got together to form a team.

At the beginning, did you guys have a coach?
Yeah, Jeff Griggs was our coach.

Oh that’s right. He’s great.
At the time I was a big fan of FourSquare at iO and wanted to also do a four man show. So it was kind of my idea and we rehearsed for a long time before we ever did a show. We had these high ambitions and wanted to really show people something new. So we’d rehearse with Jeff and he’d just laugh at us. It was probably the best thing that could happen to us, having this coach who would just laugh his ass off. At the beginning we’d challenge ourselves and make all these trivial crazy rules. Some shows we’d say every scene had to be a four-person scene. Some shows there were no sweep edits. We just had a lot of ideas of how we wanted to navigate the show. Everything has kind of transformed over the years, but you can still see parts of that. Even now, our favorite scenes are usually the ones where we’re all on stage together.

You guys have some of the most amazing transitions into theses crazy scenes, but you always manage to tie up all the lose knots at the end. It’s beautiful.
That came out of just giving ourselves weird rules. Before shows we still have a joke of, “All sweep edits, right?”

So, last night was your last show of this 7-year run at iO…
Last show of Tuesday nights, not the last show.

Ok good. Thank God. The world says, “Thank God.”

So what was last night like for you?
Oh boy. It was crazy. It’s kind of too fresh to even digest yet. I think come a few Tuesday nights from now, I’ll probably be staring at a wall wondering why I don’t have a show. But let’s see, for me, it was really just bittersweet. It was really emotional and it was also really hard. I was happy and sad at the exact same time. When we came out, the reception was so warm and I looked over and Bill’s glasses were fogging up, so that immediately got me all choked up. The show was good and we had a lot of fun, but I think the whole time I almost felt like I was floating above the show watching it and part of me didn’t even want to be in it, I just wanted watch it. There were times where we were all watching each other and then realized we had a show to do and we’d get super manic. I think we all just wanted to try and take it all it.

GregHess_LifeLongFriendsQuoteOf course, that makes perfect sense.
It’s just been such a constant in all of our lives. We started out as people who recognized the potential in each other and we respected each other comedically and then seven years later, you realize you’ve gotten your best friends out of this thing. I mean, we’ve stood up in each other’s weddings and held each other’s babies. That, to me now, is the more important part of it. The work that we’ve done has become kind of secondary to the life friends that we’ve become. That’s why I say it’s not the last show, because we are going to continue to work together in a lot of different capacities and take it to the next level.

Good. Please do. So, the “next level” is “Schlub Life,” a pilot that has gotten picked up by Comedy Central and it has you, Mark and Brendan all in it. So where did this idea come from and what has the process been like?
Around 2010, we did a Cook County show out in Los Angeles and had a meeting with Comedy Central. They said they were looking for sketch and at the time, Mark and Tim had just shot their own little pilot, “My Mans,” which Andy Miara directed as his final project for his Northwestern MFA.

Ahhh, ok cool.
They pitched the sketch and it got purchased as a pilot presentation. Then they shot the 15 minute long pilot presentation to screen at Comedy Central for a possible show. Brendan and I both got to be in that but it didn’t end up getting picked up.

However, right on the heels of that we flew back out to LA because we were pitching half hour narrative ideas which Mark, Andy and I had written together. We had an idea about writing a project for Tim and Brendan to star in. Going off that mantra of “write for your friends and write what you know.” These two guys who are irresponsible 30 somethings with really responsible wives who take care of them and all the adult elements of their lives. We thought that was a great idea for a show. Two best friends who lose their jobs and end up not going back to work and just living off their more successful and responsible wives.

Haha. That’s great.
So we went back out and pitched that and sold it off the pitch.

Wait, so when was that?
This was almost right away. Twenty minutes after we left the room at Comedy Central, we got a call that they wanted it. So we were celebrating and low and behold a few months go by and Tim gets SNL.

So this was last summer?
Yeah. I think we pitched it in April and worked on the script for a few months. Tim got flown out that summer and then he got picked up. While we were so excited for him, we also were kind of disappointed because we felt like the project was dead. But then Mark, Andy and I decided to sit down and write the script anyway and we sent it off to Comedy Central. Our agents kept telling us they liked it, but without Tim, it totally changed the dynamic of everything, so we weren’t sure. But then almost a year after we pitched it, we got a call and discovered that they wanted to make a full-blown pilot. So that’s where we are right now.

That’s awesome.
Yeah, it was really exciting.

Ok, so that’s where we are right now. You guys are heading out to LA to shoot the pilot. 
Yeah, we’ll be out there for July and most of August. The pilot shoots the last week of July/early August.

Amazing. So I’m guessing you guys are all moving out to the west coast.
We are. I think we’re all moving out to the west coast regardless even if it doesn’t get picked up. If it does get picked up, that would be great.

So Brendan is still slotted to be one of the “schlubs.”
Yes, Brendan is still in it and we are casting for the other one. If we get picked up, we can write in parts for ourselves too. So it’s been a really exciting process watching actors from all over the country reading words that we wrote.

GregHess_PilotQuoteI think that’s really true though, when they say “write for your friends and write what you know.” It’s so much more honest and you don’t have to force anything. You can literally take things that have happened in your real lives and just write about it.
Everything in the pilot is based on things that have actually happened. Brendan has an actual fear of teenagers because he was bullied as a kid. To this day, if he’s walking around and sees a pack of teenagers, he will cross the street and walk away. So, there’s a scene in the pilot where Brendan has to save some seats in a movie theatre and he gets bullied by some 14 year olds who tell him he can’t save these seats and he tries to stand
up for himself and they just eviscerate him.

That’s something that’s so easy to write because it’s a funny character quirk that he actually has. It was pretty easy to come up with story ideas because they happen all the time. Even last night at this final show, we were all hanging out and drinking to excess and Tim had a 6am flight and of course the first text I got this morning was that he slept through his flight, didn’t make it to his plane and was sitting at O’Hare drunk all day. I think his wife fully expected that to happen, so there’s that.

Haha, well of course. A 6am flight? That’s ambitious.
Yeah, and then Bill slept on my couch and we ate tacos together this morning. So yeah, “Schlub Life” started out being something we thought would be really sellable. But then we realized we actually have a lot of emotional attachment to the idea, maybe even more than we thought we had. We got to do a deep dive on our own lives.

Of course. That’s wonderful. Ok, so you and Mark are both writers and Brendan is playing the lead?
Right. Mark and I are creators, writers and executive producers and Andy is an executive producer and creator as well.

Is writing a pilot and having it produced something you always dreamed of or it’s just more of an opportunity that came your way?
It’s not something I always dreamed of. Not until a few years ago did I realize it was even an opportunity. A lot of times we see television and it seems so distant and out of reach and it wasn’t until the last few years we realized we could sell a show. The “My Mans” sell was a big part of that.

Being in Chicago, you’re in the best possible place to do the best work you could do and learn so much better than any place in the country. You get honest to God stage time and really enthusiastic and savvy audiences and the work done around town now is so good. There are so many people getting plucked out of here because the coasts view this as a really great breeding ground for talent.

It is.
And on the other hand, it’s hard to know what to do to get to the next level. We just started making trips to LA because we wanted to figure out how process worked and we wanted to be seen live. We wanted to validate that feeling like we had lightening in a bottle and we needed to package in some way, whether through a sketch show, a live show, a pilot, anything. I think you don’t necessarily have that access here, which is hard.

So if there’s one thing you could tell improvisers in Chicago who might be thinking of something like this and might not know what next step to take, what would be the one thing you recommend they do?
If I could tell myself one thing five years ago, I’d tell myself to just be prepared to work really hard. When I was 23 or 25, the improv thing was erally fun but I didn’t necessarily think of it as a career. I probably didn’t think of it as a career until I started touring with Second City and I was able to pay some of my bills. Sort of…well maybe one bill. But it wasn’t until then that I realized I could maybe do this for real.

It also depends on what your goals are. But I think having great writing samples, videos and shows you really believe in is so important. If that’s how you want to make your living and you want to show that to someone, you have to come across as a person who has a lot to say and a quality body of work. A body of work takes time to build, so my advice is not to jump out of Chicago after two years of being here and think you know it all. It’s not about the amount of time here, it’s about the body of work you have to show.

I think you’re right in saying that Chicago is not only such a great breeding ground, but that it’s also just so much more accessible. Here you can get stage time and have direct access to some of these major players who can propel you in certain ways and I think it’s much more difficult to get those things in LA.
Absolutely. We were so lucky that Cook County ended up being a great showcase piece for each of us as individuals. As a group, we were each showcased so well as individuals because we were playing with these people we had such great chemistry with. I attribute all of this to Cook County, because in terms of body of work, this is one of the best things I could show, for both myself and the other guys.

That’s what it takes. You have to bust your ass for a few years and hopefully it pays off. People always say things happen when you least expect it and when it rains it pours, which works for good things as well. I’m a firm believer in all that. What are you ultimate hopes for this pilot? Obviously to get picked up, but any long term dreams for this?
I think on a surface level, you want it to get picked up and have five seasons of the funniest televised show you’ve ever made. On a less surface level, I hope that it’s a TV show that actually has something to say. I don’t think there’s a show on television right now that talks about this time of life in an honest way. I hope that our show is super funny but ultimately relatable.

The feedback I’m most proud of is when people read it, they say, “I’ve done that,” “That’s me,” “I know what it’s like to be the only person at a party who doesn’t have a ‘real job,’” “I know what it’s like to be a fish out of water when you’re 32 years old and are still kind of doing ‘this thing.’” Whether it’s working at a temp job, living in a place you don’t like or just doing the same things you did when you were 23, that’s something that is really relatable.


So my hope for the show is that we can keep our finger on the pulse of that honesty and that little piece of truth.

So the show is based off of “schlubs” who have super responsible wives. Your wife, Holly [Laurent], is also in the improv community. When and how did you guys meet?
We met at iO. She was my level 1 teacher.

No way!
Way. Hot for teacher.

Haha, that is so perfect.
Yeah and we were actually both in relationships at the time. It wasn’t until four years later that we were out of relationships and started to date.

Were you guys friends or did shows together?
We never did shows together. We knew each other from being around the theatre and we were friendly acquaintances. I always had such high regard for The Reckoning and went to their shows all the time. It wasn’t until four years later and I passed her in the stairway of iO and asked if she wanted to go out sometime. Wait, actually, I don’t think I even asked her out then. I said “hi” and then I emailed her later.

Wait, you emailed her and asked her on a date?
Yeah…I think I asked her to go to the symphony because I had two tickets. Email is kind of cheesy, but it’s also much easier to take rejection well over email than it is person to person.

Haha. You emailed her to go to the symphony for your first date.
This is me in a nutshell. Of course, I’m thinking the symphony is a great date idea and I do it in the least romantic way, which is an email. She responded with “absolutely” but she was busy that night so we went out another night and we’ve been together ever since. So, advice to anyone who is interested in dating advice from me: email. It’s really effective.

When was that?
Late 2006. We got married in summer of 2009.

So you were dating about three years?

With your wife in the industry, does that change things for you at all? Is there additional pressure for either one of you to perform or is it just a really supportive environment?
I think it helps. I think the only pressure for us is that there is uncertainty in this profession. There are high highs and low lows and sometimes you don’t know where your next paycheck is going to come from. Stability is something we’ve learned to be better with, knowing that things are uncertain. Even with this upcoming move, we don’t know if it’ll be to New York or LA.

Do you know when?
We kind of know when. It might be August. It might be October. So the uncertainty is sometimes a struggle, but in terms of perspective, we learn lines together, put each other on tape and the other person understands how much work it takes and how to navigate that lifestyle, so it’s really great.

And the schedule. Her nights are very busy.
Exactly. Since she’s been on Mainstage, we don’t really get vacation time that much, maybe like a week every six months, if that. We have one date night per week. One night time to see each other per week, which is really crazy. That’s a really challenging job.

Mainstage is insane.
Yeah. It’s an insane schedule. Insane hours. There’s a reason people don’t stay for 10 years, because you’d just burn out.

Oh for sure.
So yeah, it’s been both a great learning experience about acting and what it entails but also a great experience because we both understand the challenges involved.

Nice. Ok, here’s one for you. So many people think improvisers are really brave and never get embarrassed. Do you have a most embarrassing moment or unexpected stage freight that you’ve encountered?
I don’t really equate it with freight anymore. I think there are unexpected adrenaline rushes I get every now and again. Now when I perform, I’m always performing with people that I know and trust so much, so it’s different. There are definitely times like when we played Bonnaroo a few weeks ago, and we’re getting ready to walk into this big top tent where 2,000 people were waiting to laugh and had never seen Improvised Shakespeare. There was a moment when I was like, “Wow, I hope this goes ok.”

How was that? What an incredible opportunity.
It went great. It was fantastic. I think there are still moments you’re hoping it goes well. In terms of embarrassing moments…

GregHess_LoseControlQuoteI mean, you email people asking them out on dates, so there has to be something…
I kind of relish in embarrassing moments. I do weird things when I’m by myself in public just to see what happens. I think if I feel like I’m in control of being embarrassed, then I actually like it. Part of why I think I even wanted to get up on stage was just to see how far I could push the idea of feeling embarrassed and having the appropriate response be laughter. It’s such a release. I think in Chicago improv training, there’s a lot of energy focused on teaching how to stay in control and mitigate losing control, but unfortunately, I think that some of the best things happen when you do lose control.

I think Cook County is a perfect example of that. You guys are so great at throwing everything out there 1000% and there is a lot of loss of control. It’s always brilliantly wound back to make sense but you can tell at the time that no one knew that was happening.
There have been times where I have been in physical pain on stage because I was trying to carry three people or something like that. So yes…

Wait. I have to ask a question. Is there an inside joke about Brendan doing push-ups because I’ve seen a number of shows where you guys try to make him do push-ups and he hates it.
We have tried to make him do push-ups on several occasions. I think it’s just because we all think it’s really funny because he can’t do a push-up.

No he can’t. It’s so funny, because you guys do everything else but then it comes down to doing a push-up and he beats around the bush so hard.
Sometimes people think we are trying to sabotage each other when we do stuff like that. But that’s an outside looking in perspective, because inside we all know certain things like that about each other and we push those buttons. For example, I don’t know anything about sports. But I’ll get put on the spot where I have to name tons of hockey players or something and I know nothing. But internally, we are trying to play up the fact that we can’t do something or don’t know anything about something else and everyone else is just “yes anding” it by pointing it out and heightening.

I love it. Ok, this might be a trick question, but who would you say is your funniest friend?
Oooooo. That’s a crazy question. They’re all funny at different times. The first person who comes to mind first is the person who makes me laugh the hardest, usually at written stuff, like a one liner or an email – we’re back to email- Bill [Cochran].

Oh my god. Absolutely. Yes, undeniably. We have this bit called “Email of the Day,” and whenever we email each other someone is awarded email of the day and he has gotten awarded “Email of the Day” more than any of us. He has such a razor sharp point of view on the world. So Bill comes to mind as my funniest friend in that way. But if anyone is going to make me laugh the hardest, it’s going to be any one of those four guys. I think that’s why we’ve played so hard together.

Alrighty, so you said you don’t do sports, what other hobbies or interests do you have?
I love reading. I love fly-fishing.

Yeah, I grew up in the country and I’m kind of a country boy at heart.

Where did you grow up?
Virginia. I love hiking, fly-fishing, kayaking, hunting…

Hunting, really?
I love duck and goose hunting.

Duck and goose hunting. That’s so funny. I’m from Wisconsin, so if people go hunting, it’s usually deer hunting.
I don’t really mammal hunt. I kind of love the country culture, which is funny because if you were to ask any of the guys on Cook County who would buy the fanciest things, it’s always going to be me. I like drinking wine, cigars, nice clothes and all that stuff. But really I’m kind of a redneck.

So you like drinking wine, do you have a drink of choice?
A drink of choice? I love rye whiskey. Most nights, I’ll have a rye whiskey on the rocks.

GregHess_DiveBarsQuoteYou talked a little bit earlier about advice to improvisers heading out to LA, is there any other piece of advice you’d give a younger improviser just starting out?
Being in the moment is such a cool improv mantra. I think being in the moment during improv classes and your first shows at dive bars for like two people is great. Honestly, I’m so nostalgic about that stuff now. Even within scenes, not being afraid to fail, reacting in the moment and not getting caught up in what is right and wrong and learning from all of it is so important. It’s a waste of time to try and model yourself after someone else because everyone has something unique they bring to the table. Everyone needs to find their own voice by being open and aware.

Where do you hope to see yourself in the next 5-10 years?
Good question. On a farm somewhere. I’d like to still be making comedy with the people I’ve been making it with for the last 10 years, just at another level, making movies and television. Half the year I’d prefer to live in the middle of nowhere, far from a city.

Nice. Do you have Holly want to have a family or is that not a conversation yet?
It is a conversation. I think it is for any married couple, but we’re just not at a point yet where we think we should bring someone into this world while we have the lifestyle that we do. But we’re totally open to it. I have enough nieces, nephews and Cook County babies to keep me company right now though.

GregHess_InsightQuoteWell, I hope you make tons of movies and television shows, because I’m sure they’ll be brilliant. My last big question for you is what is the greatest insight you’ve discovered about life and comedy?
The greatest insight I’ve discovered is that this life in comedy is a that it’s a constant balance between always being humbled and trying to show that you have a reason to be under the lights. You’re always in a state of learning something or showing something. At least that’s true for me, I’m always bouncing between those two things.

Alright. Any final comments Greg?
Email. It’s a fabulous tool for dating and business relationships. My final comment would be that
email is the wave of the future.

Email is the wave of the future. Words of wisdom from Greg Hess.

*There will most likely will be a one-off Cook County show at the end of August.


Greg Hess is a founding member of Cook County Social Club and Improvised Shakespeare Company. He has performed with the Second City national touring company, Baby Wants Candy and the iO Theatre among others. He has been a featured performer in the TBS Just For Laughs festival and is a contributing writer for the Onion News Network. He has developed written material with Playground Entertainment, Jaime Kennedy Entertainment and Comedy Central. Greg is a graduate of the College of William & Mary, and studied at the iO Theatre and the School at Steppenwolf. Currently he is working on “Schlub Life,” a pilot he co-created at Comedy Central.

Interview conducted on June 26, 2013.

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