Until recently, Ryan Mason was regarded to be among the funniest stand-up comedians in Milwaukee. Sadly, that’s no longer the case. No, the quality of Mason’s slanted observations on everyday existence—which yielded lucrative opening slots for noted national comics like Joe Mande, Morgan Murphy, and Kevin Bozeman—hasn’t diminished in the slightest. Instead, the former Milwaukee Midwest Comedy Stand-up Competition winner’s move to Madison in March took him out of local contention and left Milwaukee comedy worse for wear. However, the three-plus-year vet of Milwaukee stand-up still returns to perform periodically, and still produces a monthly showcase at Vino 100 in the Third Ward.

Tuesday night, Mason will return to town for his biggest show of his young and promising comedy career, taking Turner Hall’s stage as Kumail Nanjiani’s opener. Before the Milwaukee ex-pat’s most important 20 or so minutes of stage time yet, Milwaukee Record called up Mason to talk about the differences between the Madison and Milwaukee comedy scenes, how he landed the opening opportunity, and what the gig means to him.

Milwaukee Record: You haven’t really lived in Madison that long, but are there any differences you’ve noticed between that scene and the Milwaukee scene?

Ryan Mason: The people, like myself, who are trying to break into comedy have most of their stage time directed towards one place, The Comedy Club On State. I would say that The Comedy Club On State—from what I’ve seen and what I’ve heard from touring comics—is one of the best places in the country to do comedy, just because the built-in audience is so perfect. In Milwaukee, there’s a lot of great shows going on throughout the city that are being put on that cater to more of the indie scene, with more underground shows. You have shows that sometimes cater to a little bit of an older crowd. [In Madison], all the great shows here are in one place, which puts everybody in one room and raises the bar.

MR: I know that you’re bouncing back and forth, but now that you’re gone and it’s not as accessible, are you realizing you miss certain aspects of our scene?

RM: Yeah, absolutely. I miss the sense of community there. Having been a part of the comedy scene in Milwaukee for over three years, you get so used to faces, you get so used to rooms, and the way the crowds react to your jokes. I could see all my friends on a Tuesday night at an open mic. I miss all the comics the most. I miss my friends.

MR: Unlike the way that it seems in the music realm—where there’s a definite split between Madison and Milwaukee—in the world of stand-up, I’m aware of Madison comics like Chris Lay and Nick Ledesma from watching them perform here at places like Karma and the Cactus Club. It seems like there’s a lot more overlap between the two cities in comedy than in music. Is that accurate?

RM: I think there’s a lot more carryover because there are guys coming from Milwaukee to Madison to do the comedy club here and they’re meeting new comics. All the guys in Milwaukee are producing shows and are able to bring people from Madison to Milwaukee. Milwaukee is really blessed that they get to see not just the people that are really good in the city. There are people curating shows are really just looking for the funniest people.

MR: On to this show. I might be wrong, but I feel this is the biggest show you’ve had to this point. How did this opportunity come up?

RM: I would agree that it’s probably my biggest show. Kumail has a show on HBO that he’s super funny in. In terms of the opportunity, Turner Hall has been really good about keeping in touch with me. I did a show there and had a great time doing it. I kept in correspondence with the people that book at Turner and let them know my availability and that if there was anything coming up, please let me know. Shows came and went, but they recognized this show as one that would be a good fit for my style of comedy. They actually pay attention to what the night is going to be like.

MR: I agree. It seems like a really good match in terms of what you do on stage and what Nanjiani does.

RM: I don’t want to call myself a nerd because so many nerd things are cool now, but Kumail has focused on topics that would have traditionally been called nerdy. I’m a guy who played Magic: The Gathering growing up and definitely played role playing games, and he’s been on shows and podcasts talking about things like that. He’s doing a podcast now about The X-Files, which was one of my favorite shows. So in terms of that type of background, that’s our commonality.

MR: As an indie name and as a guy who holds down a regular job, what’s the importance of an opportunity that lets you play in front of an audience at a venue like Turner, and being able to add another notable name on the list of people you’ve performed with? What does the opportunity mean for a person at your level?

RM: Having done the room before, I can say it’s not as nerve-racking going into the situation, but it’s still exciting. I’m super excited to be in front of people who haven’t seen me perform before. I’m also excited for people who have seen me before to see me on a bigger stage. The most exciting part about it is getting to perform with people I know are super funny. In terms of me building some sort of momentum or career out of the work I’m doing, more people seeing you helps. It’s a great opportunity because I believe in the shows at Turner Hall, I know that Kumail Nanjiani is a funny, funny guy, and I know he has a huge audience of people who respect his work. For me, it’s about getting myself in front of those people too, so they can remember my name.

I think in the long run, comedians look for these opportunities, and when they show up, you just make sure you’re ready. You live your entire life waiting for somebody to make the call to say “Hey, are you ready for this show?” and when they say it, you stand up and you say yes. Then you go out and kill it because that’s your job. I’m not as nervous this time around, I’m just really excited to get back in there and be part of a really fun night.

Ryan Mason opens for Kumail Nanjiani at Turner Hall on Tuesday, June 17 at 8 p.m. (7 p.m. doors). Tickets cost $20.

About The Author

Avatar photo
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.