This Week In Web Videos: ‘Shrinkage’

“Mom, dad. I want to be a comedian.”

Chilling words. Words that may be every parent’s worst nightmare, not necessarily because moms and pops hate laughter, but because a comic’s life is a hard one — often replete with substance abuse, loneliness, and the kind of poverty that stops being cool around your 476th cup of Ramen noodles.

I’d guess that very few parents want their kids to go into comedy, unless they’re in it themselves. That’s precisely the case for Tyler Alexander, head honcho at and the heir to a Chicago comedy empire started by his dad, Second City co-owner and CEO Andrew Alexander.

Whether or not Mr. Alexander ever cautioned young Tyler about the pitfalls of making people laugh, we can be sure he exposed him to much of the business’s glory — glory that Tyler has channeled into a delightful web series called Shrinkage and an exciting effort to make the Internet chuckle Chicago style.

What is your role in relation to this series? And to Second City? 

Tyler Alexander: I’m the vice president of the Digital Media Department. I work on the biz development side so, with the relationships and the potential partnerships we have in that space and then I also am an Executive Producer on the creative side. I end up having final creative say in a lot of the projects but I end up trying to give everyone a really big box to play in.

Tell me about how you got started in the comedic space and your background. 

So I’ve been involved with Second City since I was about six years old. My dad owns the company so my dinner table conversation had to do with Second City and improv. I pretty much grew up with the brand and it’s basically been a part of my life for as long as I can remember. That’s really what my comedy background is. I’m not a performer. I have taken classes but it just doesn’t really interest me. I knew from a pretty young age that I wanted to stay behind the curtains. The way that I got started with this show is: I was working out of the LA office that’s where we had originally decided to run The Second City network, this digital video initiative. So I started working in production over there and eventually I had the opportunity to take over the department and that’s how I found myself in this position.

How did Shrinkage come about? 

We actually shot a couple of videos in partnership with the Lyric Opera and it was basically the exact same premise as Shrinkage. And then I took another look at what we had shot with the Lyric and I was like “We can’t let this die, we’ve got to do more.” So we’ve got these quarterly writer’s development rooms and myself and production basically cast the room, writing more episodes of it in that same vein.

How would you say that the Second City comedy scene differs from the UCB, the Pit, The Magnet, The Groundlings — all these other hotbeds of improv comedy?

I think our difference is: We use improv as a tool to write sketch comedy. The other theaters all have a slightly different approach to improv and I think the biggest thing for us is to use improv to make actual written material. UCB, Groundlings, The Pit, IO, it’s all just improv shows. At Second City we do have improv shows playing in our theaters and we do have improv in our sketch shows but, most of the work we do is scripted.

Do you think there’s an advantage to that or is that just how you guys have developed? 

I think the advantage is improv is fantastic and it’s an important piece to the writing process but if you’re using improv to build something in front of an audience you really have an opportunity to focus in and make something better and better and better each night. It’s almost like a trial and error situation if you’re re-improvising each night. Whereas if you’re just doing a straight improv show there could be a missed opportunity.

How are you guys using this new digital arm to take advantage of a quickly moving web comedy market?

Tyler Alexander: The biggest thing for us when we re-launched the Second City was being true to the brand and basically making funny and engaging comedy that is satirical, topical, and comes from different points of view. We had a real mission: On the production side we wanted them to look good and on the written side we wanted to make it easy to read. We’re doing both and it’s all featured on the Second City Network but the competition is rife. There’s a lot of content to be consumed, people have a ton of options. But at the same time a lot of comedy  is moving is online so we’re trying to stay with the game.

What’s the biggest challenge in creating web content? 

I think it’s getting it right the first time. When we’re putting up a sketch show it’s a weeks-long process of trial and error in order to get it right. When making a video, we need to make sure that it’s going to be well received before we actually release it. We do our due diligence in the writing process to do re-writes when we have to, but we’re not really going to know until we release it.

Is there any kind of trend for what’s successful and what’s not or is it just catching lightning in a bottle? 

You hear a lot about the number of views but for us the most important thing is actually creating something we’re mostly proud of and feel good about. If we can sit back and say, “Yeah that’s funny to us and we hit all the check marks and it looks good and makes us laugh.” I think a lot of people in the digital space look at impressions and the click through rates and that’s success for them but we’re not really interested in that. Trying to build a foundation and find our voice is the biggest thing.

What advice do you have for people who are looking to get in the web comedy space but don’t have a foothold in it yet? 

I think it’s just doing what you want to do. It sounds silly, but if you’ve got a camera and you know how to edit something you can put it together. Funny or Die and we even aggregate content, but there’s a ton of websites that do that with short form comedy videos. The Kill All Comedy folks will get an idea for a video and they’ll shoot it, edit it, and then put it out there and the shit’s fucking hilarious. Conner [O’Malley] has written some stuff for us, but his video work with John Reynolds and those guys is amazing.

I think it’s a hurdle that a lot of people have trouble getting over. 

If you’ve got something that you believe in and you feel passionately about, that should reflect in the video work itself. If you’re over thinking it and trying to think about crazy clash of context videos that are also topical, it’s going to be difficult.

  1. Frame
  2. Pop culture commentary
  3. Performances

Episode #1: Three Little Pigs in Therapy

I’ve addressed it many times before but the first step in creating a good web series is creating a sustainable web series — both in terms of creative possibilities and budget. Sustainability comes from choosing a framing device, or “container,” that provides an easy to understand backdrop for countless episodes. It’s even better if that container can be housed in one cheap location.

Episode #2: Homeland Carrie & Saul in Therapy

Relatability is key. Making incisive use of broad pop culture references is a good way to get people on board.

Episode #3: Mario and Luigi in Therapy

In the venerable tradition of Second City alums like Dan Akroyd, Chris Farley, and Gilda Radner… these actors are really talented, and that never ever hurts.

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