Greg Hess

Greg Hess is a man of many comedic talents. He's a 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." Greg and Cook County member, Mark Raterman, created, wrote and will now be producing this pilot starring, fellow Cook County member, Brendan Jennings, for Comedy Central this summer. Greg made time in his bustling schedule to talk with me about the process, production and inspiration behind this pilot.

Where did the idea for "Schlub Life" 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 [Robinson] 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 [Jennings] 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.

[Laughs] 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. 20 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 Saturday Night Live.

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. It's been a really exciting process watching actors from all over the country reading words that we wrote.

I 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 at our final Cook County show, we were all hanging out and drinking to excess and Tim had a 6 am flight and of course the first text I got the next 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.

[Laughs] Well, of course. A 6am flight? That's ambitious.

Yeah, and then Bill slept on my couch and we ate tacos together in the 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 really 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 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 butt 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.

To read the entire interview with Greg, visit

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