During his four years on stage, Gary Zajackowski hasn’t shied away from taking his material to strange, off-putting, and occasionally very alienating places. The unofficial wild card of Milwaukee comedy’s body of work finds him jumping from obscure baseball references to loaded bits about skull-fucking to announcing his desire to get in more fights—all within moments of one another. Turns out, Zajackowski’s comedic cornucopia also includes a wealth of knowledge in regard to cartoons and video games, which has yielded geek-themed gigs at 42 Lounge’s quarterly Cthulhu’s Comedy Collective and Madison’s Wizard Con back in February.

Saturday evening, Zajackowski will be part of a special installment of Cthulhu’s Comedy Collective in the Brookfield Sheraton as part of this year’s Midwest Gaming Classic. Before the unpredictable Milwaukee funnyman unloads his arsenal of gaming-related gut-busters on an unsuspecting audience, Zajackowski told us why he loves performing at conventions, the importance of trying to relate to audiences, and about the time he did crowdwork to a dude dressed like Goku.

MR: Not including Jake [Kornely]’s roast, I haven’t seen you since, I think, your Comedic Release Show last summer. What have you been up to over the course of the last 12 months?

Gary Zajackowski: Just doing a lot of open mics. I just did the [Madison’s Funniest Comic] competition in Madison. I did two competitions in Milwaukee. I think I’m done with competitions though. I say that, but I don’t know.

MR: And you did a convention in Madison, right? What was that like? Did your material end up going over well?

GZ: Yeah, [Wizard Con] was awesome. That was fucking great. It went over super well. The focus was supposed to be nerdy kind of humor, and we had some of those jokes, but then we worked in some of our other material. It was Jon Kuderer, Patrick Tomlinson, me, and Lisan Wood. It was like doing stand-up at a Halloween party, but there was a specific focus to most of the costumes, so I was doing crowd work to a guy that was dressed like Goku.

MR: Did you have anything loaded up ahead of time? Like, did you have something ready to go if you saw somebody dressed like Waluigi or something?

GZ: Totally. Actually, the guy that was dressed as Goku, I saw him walking through the parking lot when we got there. Some people spend hundreds of dollars on their costume, just to walk around, be seen, and take pictures with people. It was awesome, and they were down for stand-up.

MR: And you—and Patrick, again—are doing something very similar around here this weekend at the Midwest Gaming Classic. I don’t think they’d ever incorporated stand-up before. Are you planning to use a lot of the same jokes you did in Madison and when you did Cthulhu or will you try out some new stuff?

GZ: I’ll probably do a lot of the same jokes. It’s material I feel won’t go over well with most crowds. There are references that will just be lost on people that aren’t into specifically nerdy things.

MR: But the people who are will probably lose their shit.

GZ: Yeah, if they hear a reference to Portal or something, but people who play Portal and love it will probably go crazy for it.

MR: That’s essentially the beauty of the event itself. With the myriad of options that it offers, there’s something to serve almost every gamer. Some people are only into pinball, some people only like Atari Jaguar. That seems to be the case with types of humor in this showcase. You’re into gaming. Patrick writes Sci-Fi novels. Liza [Marie] might do stuff about comic books. There should be something for almost every interest.

GZ: Exactly. It kind of fans out. There are people who like video games who don’t read comics, and people who are into Lord Of The Rings and fantasy kind of shit who aren’t into games. But I think everyone is at least aware of the other things. The Anime kids know about tabletop games and stuff, you know?

MR: And on the other side of things, I’ve seen you go into really specific bits about baseball. You don’t seem to be afraid of alienating people.

GZ: Yeah. You try to use a reference that’s somewhat universal, but there’s maybe an esoteric aspect to it. Then you just have to relate the idea in such a way where people will get where you’re coming from and you won’t leave anybody outside. You try to include everyone, even if you’re talking about something that’s outside of their realm. That’s the idea. If I say Portal, people who play video games will probably at least be aware of it.

MR: Off mic you mentioned you’re working on a podcast. Is that far enough along to talk about?

GZ: I’ve been taking…I call them field recordings. I don’t know if that’s the proper term for it, but I’ve been recording people in more candid moments—co-workers and just people out in the world and I plan to do some sort of compilation thing with commentary in between people talking about Bronies, war stories, and other stuff to just capture something interesting. It’ll probably but out over the summer.

MR: What was the experience of filming your “Having A Few” like? Yours is in my top two, definitely.

GZ: That was fun. I don’t even remember how I got home that night. They ask you a question and you start shooting off at the mouth until you find a point that’s just a snapshot of the night.

Gary Zajackowski will perform Saturday, April 11 as part of the Cthulhu’s Comedy Collective showcase at Midwest Gaming Classic. Christopher Schmidt, Liza Marie, Jason Hillman, Alex Anderson, and host Patrick Tomlinson will also perform. The show begins at 6:30 p.m.

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Co-Founder and Editor

Before co-founding Milwaukee Record, Tyler Maas wrote for virtually every Milwaukee publication (except Wassup! Magazine). He lives in Bay View and enjoys both stuff and things.