Saturday night, live and localized late night talk show The Goodnight Milwaukee Show and the Tall Boys improv troupe will perform together in an instance of multifaceted comedic collaboration. While both groups are under the vast umbrella of humor and each is out for laughs, Good Night’s roots in stand-up and sketch don’t have much in the way of overlap with the Tall Boys’ tendency to fly by the seat of their pants. The musical equivalent of this rare merger would be a rapper, a metal guitarist, and classical pianist forming a ska band. In sports terms, it’s akin to the Brewers and Bucks coming together to play ice hockey against the Packers. It’s a coalescence of comic styles in which nobody involved will reside entirely in their comfort zone.

However, the two performers who will be closest to feeling at ease in the endeavor are Erik Koconis and Lee Rowley, both of whom happen to be regular contributors to The Goodnight Milwaukee show and Tall Boys alike. Before the (likely) one-time spectacle of stand-up, sketch, and improv wrapped in one tight package takes the stage this weekend, Milwaukee Record asked them how the unorthodox event came to be, what (they think) we can expect, and how exploring different comedic avenues aids in development.

Milwaukee Record: How did the decision to do this type of merger show come about? Whose idea was it, and what was the original response?

Erik Koconis: That would be me. This is the second of two mash-ups that were started. The first one, with Sketch Marks, was a blast. I remember we were sitting after rehearsal and we were looking at November and we didn’t have anything scheduled. We didn’t just want to do another Tall Boys show. They’re super fun, but we wanted to try something a little bit different.

Lee Rowley: I think the desire was to make it a little bit easier on ourselves as far as promotion goes. The more people that are part of the show, the more people know about it. That was the case with the Sketch Marks show, plus it was a benefit show for the Hunger Task Force and it went really well. It was a two-night show at ComedySportz, and that was sort of our impetus into doing it with The Goodnight Milwaukee Show.

EK: As soon as we asked, both group said yeah, and that kind of enthusiasm makes collaborating so much easier. Everybody is on board for a production that we’ve never done before.

LR: Everybody contributed to the monologue jokes or had input on that. We’re going to do an improv set at the beginning of the show. Then, some of the desk pieces were written by our director Jared [Stepp] and [Goodnight Milwaukee writer] Greg Bach. We’re all going to be in a sketch at the end, a hilarious sketch written by Chris Schmidt.

EK: The funniest man in Milwaukee.

LR: The last rehearsal and the rehearsal before that have been so much fun because it’s been all these very funny and talented people contributing, allowing for new ideas to take place, improvising, writing some stuff. It’s really been cool.

EK: It’s been a complete collaboration all the way through. The Tall Boys have come into the writing sessions—which has kind of been a culture shock for the rest of them, I think. And it’s a shock for some of the Goodnight Milwaukee guys.

MR: Yeah, they’re involved in stand-up, but are you planning to have them involved with any improv?

LR: No. The Tall Boys will kind of have their own 20-minute improv set at the beginning of the show, but then I think we’ll be able to successfully merge that with the monolgue and sketches.

MR: So everyone sort of knew their role and went with it? Was there anybody who ventured into any new, unexpected areas? Like a stand-up leaving room in his set to improvise?

EK: A little bit. There was a little bit of push-back in the beginning when we did our pitches for all the monologue jokes. The Goodnight Milwaukee guys will write for a month and a half, then they come to the Tall Boys side of the rehearsal which has nothing prepared at all. That was a discussion that we had. The Tall Boys didn’t want to listen to the monologue jokes that were picked because it might influence their improv. And at first, monologue jokes pitched by Tall Boys weren’t taken as seriously because they weren’t written by a stand-up.

LR: Yeah, Erik’s right. There was a little bit of that culture shock, but it came together really well, and I think it’ll be really fun. I’m excited.

MR: Do you think that this will maybe breed even more collaboration in the future? Maybe a show with Broadminded or a merger with Ragtime? Something like that?

LR: I think so. We’re five guys who are pretty easy to work with.

EK: Every show is better with Tall Boys.

LR: Whether you’re talking about the beer, the group, or some variation of the beer and the group. No, that would be great because sometimes it’s so hard for us to schedule a show. All five of us are so busy with separate projects, but when we can help, and commit, and work with another group, it just adds a different level to it.

EK: I really hope it continues—even if we’re not involved. If two other groups decide they’re going to do a mash-up show, that would be so cool to see.

MR: What’s the relationship between improv, stand-up, and sketch, if there’s even any? Do you think one style informs another?

EK: Do you mean as an art form?

MR: Like if you’re an ardent stand-up who goes outside of your comfort zone and investigate sketch or improv, can that help you?

LR: I think any type of reaching outside your comfort zone will only help you. In terms of performance, I don’t think any new thing that you try will ever hinder you. Stand-up can be very regimented. It was really nice doing some stand-up because there’s a certain rigidity and a certain structure to it, which forces me to think differently about stuff. It has been helpful in my improv because it’s definitely given me more discipline towards some things.

EK: And it’s the exact opposite for me. I started in improv, but for the last 10 years, it was just stand-up. I had a really regimented set. As soon as I engineered a bit, it was a fully constructed paragraph I would say word for word every time. The trick with that is when it doesn’t work, then you’re caught. Either you have to reveal your true self—which for a stand-up is probably one of the most terrifying things in the world—or just hope you can plow through it. Those are your only two outs. Going back into improv, it gave me more confidence in just being a performer on stage without material. I still have the material. That’s always in my back pocket, but now I don’t have to repeat the bits verbatim. I know the concepts and I can translate that in a multitude of different ways depending on who I’m talking to. That’s something that I’ve learned with improv. You have the idea, and you have to build off that. In that sense, it’s been amazing how it’s impacted it.

The Goodnight Milwaukee Show and Tall Boys will perform together Saturday, November 29 at ComedySportz at 8 p.m. Cover is $8 in advance or $10 at the door.