If you follow Milwaukee comedy, you almost certainly know who Ryan Holman is. The funnyman’s relaxed witticisms are regularly put on display in monthly showcases, in opening slots for touring comedians at Comedy Cafe, and during the periodic Cactus Club comedy shows he produces. That said, you’re almost as likely to know Ryan Holman if you DON’T follow comedy. The comic routinely tosses his well-crafted puns and absurdest one-liners to the drunken wolves captive in situations not necessarily conducive to comedy, as the in-house humorist at other events that sometimes drastically clash with conventions of traditional stand-up. He’s opened or emceed for bands like Trapper Schoepp & The Shades, Blessed Feathers, and The Fatty Acids everywhere from intimate bar back rooms, all the way to the Pabst Theater. This weekend, Holman will perform what looks to be his most challenging gig yet—two between-band sets at an outdoor festival in the light of day. Before Holman faces the crowd and fights with bands, booze, and mozzarella making demos for attention at Brady Street FestivalMilwaukee Record caught up with the comedian who seems to thrive in difficult settings.

Milwaukee Record: It seems like you do a lot of unusual gigs. For every time that you go up on stage for a regular open mic or showcase, you’re also opening for Blessed Feathers at Pabst, producing the Cactus Club variety shows, and now doing local festivals. Why do you choose to do these unorthodox types of gigs more often than traditional stand-up shows?

Ryan Holman: I think it goes back to my appreciation for music. I like bringing those two worlds together because I can appreciate comics and appreciate bands, so why not try to do it together? Initially, when I started opening for bands or going on between bands, I did it because I realized the music scene in Milwaukee was so much bigger than the comedy scene—like, four years ago—and I was making more friends in bands because I was going and supporting a lot of local music, while I was doing my thing on the side.

I like the feeling of going up in a room that’s chattering and waiting for a band, and they’re really loud. After you get a couple jokes in and people are quieting down, the feeling of shutting a room down and making everyone laugh is invigorating. It’s great to go up in comedy clubs too. I don’t want to say that it’s too easy, but people there start silent. They’ve paid to see you, and if one person talks, they’re told to shut up. Whereas when I go up [in a non-comedy setting] and people might be talking for most the show, but if half of a room of 100 people that were expecting to see music sees you and they like you, they’re going to remember that. It’s a challenge.

MR: Do you need to adjust your usual style to adhere to these new situations? For example, do you work faster, speak louder or maybe not wait as long between punchlines?

RH: It’s always case-by-case. I feel like the overall pace might be a little quicker. You can’t really lag. I just try to cut out the fat. That’s what I all about anyway, though. I don’t tell a lot of stories. Everything that came to me as a story, I cut down to be as short as I can. I don’t like talking for a long time without making people laugh.

MR: Do you think these potentially difficult situations have helped you develop more as a comic? Have you been able to apply the lumps you’ve taken from crowds not prepared to see comedy to help you in the traditional stand-up format?

RH: To be honest, I enjoy it. I choose wisely on shows, so I’ve never had a particularly bad situation. The worst thing I ever had was one of the Cactus Club shows I booked and was super-excited about just so happened to be the same night as Brady Street Festival, so we had like 15 people show up. So this year, I’m performing there.

I go into all the alt rooms—opening for bands, and hosting a show I booked for bands—most of the time, 80 percent of the people there are coming for the bands. With those, the friends or fans of the bands don’t know there’s going to be a host, so I just go into it knowing that. I’ve learned to talk over people and then what usually happens is little by little more people will listen. At the club, when you walk on stage, it’s quiet and people applaud for you before you’ve said anything. I love both settings, but I more a kick out of these other gigs. Most of the people at indie rock shows probably aren’t going out to comedy clubs.

MR: So you’re bringing the comedy club to people who won’t explore it on their own.

RH: Exactly, that’s what it’s always been about. There are people who would only go to see comics only who now get to see bands, and there are people who normally only see bands who now love certain comics in this town. I’ve watched the scene grow a lot over the last couple years—with more open mics and new showcases—but it’s really cool to see bands ask other comics to open for them and host. There’s a lot of cross-pollinating. I like that it’s bringing people together. It’s cool that so many opportunities have come for me just because I stepped out of a normal comedian’s comfort zone.

MR: You mentioned that Brady Street Festival messed with your Cactus Club show last year. Did you reach out to them this year or did they approach you?

RH: I had just done the Pabst show and I thought it was the best thing ever. It was the coolest opportunity of my career, and I thought it would be impossible to ever get another show as cool or big as that this year. Then a week later, [Brady Street Festival organizers] emailed me and asked if I would be open to doing it. I’m opening for Kane Place [Record Club], which is one of my absolute favorite bands to watch in town and a bunch of really cool and fun guys, then Celebrated Workingman, who is doing a reunion show.

MR: What can we expect to see you do on Brady Street this weekend?

RH: I have a trick or two up my sleeve—something that I haven’t done before and I feel this is the place to do it. I try to do that for every certain big show. I have some new jokes that I’ve only told on stage one and some old stuff, so we’ll see how it goes.

Ryan Holman will perform at Brady Street Festival on Saturday, July 26 at 6 p.m. and 8:30 p.m. on the Brady Locals Stage. He’ll also appear at the monthly Comedy Cafe open mic/showcase Wednesday, July 30.

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