This Week In Web Videos: ‘Sad Boss’

There are lots of web series on the Internet. Few will capture your office mates’ attention and have them laughing out loud in under 30 seconds. This one will (assuming your office mates don’t completely suck). That’s because creator and star Mike Cullen has artfully mastered the ways of deadpan alt-comedy, the kind of stuff that makes me love Will Ferrell’s “Worst Boss Ever” (sorry about the vintage video) sketch more than my own parents and strikes fear into the hearts of anyone who watches anything on network television. Prepare to be tickled, and a little bit upset.

Tell me about your comedy background. 

I’m from the south side of Chicago and I’ve been doing improv since I was a sophomore in high school. I started making YouTube videos by the time I was a junior. By now, we have 80 videos on YouTube, I’d say. I took 2 years off from doing improv and then I did the Comedy Studies program at Second City when I was a junior in college, and from there I joined Columbia College’s improv team.

How did this series come about? 

I was looking to do something on a bigger scale. Some teachers from Columbia were also willing to help me. I wanted to come up with the simplest idea possible for a web series and I thought using a workplace setting would be something people were already familiar with and I just wanted to make them very, very short. I also really had the desire to play a character that was the most unlikeable and despicable person. Just so over the top. The people I liked in comedy always played characters like that.

Who are your comedy influences?

There’s definitely a lot, but the main one right now would definitely be Eric Andre. The Eric Andre Show is probably the funniest show on right now. Performers, I would say Will Forte in Macgruber. Just because he’s so pathetic and it’s so funny to see a character cry. I got to see Tim Robinson perform a few times at IO and no one plays a better idiot than he does. I like a lot of Adult Swim shows. Eagleheart, Tim and Eric. I like characters that are broken men.

What was the biggest challenge with this series? It seems like it came together pretty easily, was that the case? 

It did come together pretty easy because I have a group of friends that I’ve been making videos with for a while and are great. The hardest part of the process was the editing. There was the temptation in some of the episodes to make them longer, like the 3rd episode. But there weren’t a lot of cases like that. We shot a lot of footage, so I knew from the beginning that we were going to have to cut out a lot of stuff. I’m happy with the final product because some weird stuff was still able to get in there. We shot the whole thing in basically one day and it took us a month to a month and a half to edit.

What advice do you have for people who are looking to get into the web space but don’t have a ton of experience? 

I would say that experience is a little overrated, I think if you have the desire to make something you should do it and not let anything hold it back. I think it’s a waste of time to worry about whether or not something is good or bad. Worry about making something that’s not boring. Certain people will watch Sad Boss and say that it’s absolutely terrible but I’d rather have them say terrible than boring.

So be bold in either direction, basically? 

Yeah, and I have a Vimeo account where I put my videos and a lot are really poorly made and experimental and I don’t really care if everyone loves them, because they were just fun to do. People should just do what they enjoy rather than worry about if they have enough experience. Sad Boss is something I did put a lot of work into, but it does still have my style of jump cuts and things that don’t make a ton of sense.

What’s the best way to make people aware of your work? 

I feel like that’s something that I still need to wrap my head around. This is the first time that I reached out to people about a video. I just sent it to you guys for the hell of it and didn’t really expect a response. I can’t fully answer this question because I don’t think I am that good at promoting myself.

What steps are you taking to get better at self promoting? 

I want to keep working with more and more people and grab the attention of people who are making series, just because I’m young and it’s hard, so I’m trying to learn that myself. I did my last semester of school in LA and came back here and made these videos, but I want to go back to LA and learn how to self-promote and meet people and show my videos to anyone and everyone who’ll watch.

1. Anger

Nothing’s better than seeing a physically adept comedian play a middle aged man who is getting very pissed off.

2. One-note jokes

Cullen’s discovered the beauty of the blackout sketch. Who needs variety when one really good joke will win the day?

3. Anti-comedy

It’s so not funny, it’s funny. Pulling that off is no joke.

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