If you go to comedy shows in an around Milwaukee, there’s a good chance you’ve seen Raegan Niemela. Not only has the Milwaukee (by way of Michigan’s Upper Peninsula) comic become a fixture in the local scene over the course of her seven years of standup, she’s also opened for the likes of Kyle Kinane, Nicole Byer, Carmen Christopher, and more. Along the way, she’s also performed in comedy festivals all over the country and headlined clubs throughout Wisconsin.
Every month, Niemela also takes the stage at Cactus Club as the host of Cowboy Killers, a showcase she produces. In advance of this month’s edition (which will take place at the Bay View venue on Wednesday, November 6), Milwaukee Record caught up with Niemela to talk about highlights from her comedy career so far, the development of Cowboy Killers, and some short-term standup goals she hopes to put into motion in 2025.
Milwaukee Record: The first time I saw you was when you were hosting for Kyle Kinane at Comedy On State. It seems like you’ve been doing a lot of cool and memorable things in comedy ever since. What are a few of the standout moments from the last five years?
Raegan Niemela: Yes, that weekend opening for Kyle at Comedy On State really got the ball rolling for me in comedy. You can still see me in a Christmas sweater I decided to wear in March for no good reason bringing him onstage at the beginning of “Trampoline In A Ditch” on YouTube. I look 12. But since then, last fall was most memorable for me. I got to open for Kyle and Nicole Byer separately at the Pabst Theater in a span of like 30 days. It was an incredible affirmation of how far I’ve come in the seven years I’ve done comedy, as well as how far I’d like to go. Mostly because I called my dad both times I was working the Pabst, and he simply said: “Oh, nice, honey. That’s cool. Have a good show!” Gratifying and humbling, all at once.
MR: Between racking up great opening credits, performing at festivals all over, and headlining rooms around the Midwest, you also started Cowboy Killers. Can you talk about how this showcase came about and how it’s gone so far?
RN: The showcase came about as a suggestion from Carmen Christopher, who I opened for last fall at Cactus Club. He loved the venue and suggested to the owner that a local showcase start running there. I happened to be standing next to him and Kelsey when he brought it up, so it was kind of just “the right place at the right time” situation. The shows have been going extremely well. I’ve been able to have a lot of phenomenal locals headline, and recently started booking both Madison and Chicago comedians as well. I think the goal is to get the show to a place where comics I’ve met at festivals who are touring through the Midwest can come in and headline—especially if they’re not at a level where the local clubs would book them to headline a full weekend. I have met so many cool people during those fests, and would love to bring their talents into Milwaukee.
MR: Cactus Club is mostly thought of as a music venue, but they’ve been landing some accomplished comedians like Sarah Squirm, Carmen Christopher, Connor O’Malley, and Mike Hanford of late. What makes Cactus Club a special space for comedy and for Cowboy Killers specifically?
RN: I don’t have a hand in booking those comics, to be clear. That’s all Kelsey. But I know that those folks want to work with her at Cactus because it’s an independent, female-owned business that has deep roots in serving its community. There are not a lot of independent venues left, especially in comedy. The mere fact that the venue exists, let alone is run by such phenomenal staff, is attractive to any performer.
MR: Can you talk about the November 6 show? What can people expect for each of the comedians?
RN: The November 6th show will have a lot of my current Milwaukee and Chicago favorites. The guest spot is Evan Pack, who is a fairly new up-and-coming Milwaukee comic that I very much enjoy. The features that night are Alecia Altstaetter and Ray Roberts. Alecia comes from the Milwaukee improv scene, so it’s always fun to watch her standup because she brings a lot of those talents from improv into her standup routine. We did a VFW hall last summer and she absolutely murdered in front of an audience that was 65-plus and mostly hammered in a way I don’t think anyone else could. Ray Roberts is originally from Ohio, but lived in Milwaukee for a time before moving down to Chicago. I love watching Ray do comedy because he seems equally exhausted and in love with it at the same time. Nobody talks smack like Ray. And lastly, our headliner will be Ton Johnson who is now living in Chicago after a long career in Milwaukee. Ton is quite literally one of the first people to speak to me after my first open mic. He has been a moving goal post I’ve been chasing in comedy for year. There aren’t many other folks doing it in the Midwest I admire as much as him.
MR: I should mention it’s also the day after Election Day. Do you think the timing will impact the show? Or do you hope people will be ready to laugh?
RN: I honestly have no idea. I hope people will be ready to laugh. These few weeks leading up to it have been so tense that I feel people need catharsis one way or another.
MR: What are some goals or plans you have for Cowboy Killers in the near future? Any dream comics you’d like to book? New venues or audiences you’d like to bring the show to?
RN: The next plan for Cowboy is to move it back home to where I started comedy: Riverwest. Starting in January of 2025, the show will be booked on a monthly basis in The Falcon Nest at Falcon Bowl. It was originally a greenroom for the main stage in the hall that they’ve renovated into a speakeasy. I love Cactus Club so much and am so grateful to Kelsey for letting me start the show at such a kick ass venue, but this feels like the right move for what I have in mind as the show goes forward. There are so many folks I’ve met on the road I would like to come headline in Milwaukee. First that comes to mind is Kate Sisk, who just came through and put together a show at Sugar Maple. But I don’t want to spoil anything. Stay tuned next year, and hopefully we’ll have some of those comics I’ve met in Alaska, Atlanta, Denver, and more in the Cream City.
MR: Beyond the monthly Cowboy Killers shows, what else do you have coming up? Anything you’re especially excited about?
RN: Not at the moment, which is kind of a relief. I’m in a bit of a plateau in terms of my development right now. I’m looking forward to a few months of writing bad material. I think I need to flesh out a new angle, or maybe expand upon the one I currently have. A lot of my stuff is based on my family and dating. One thing I’ve struggled to do is write about things that are impersonal with my voice, and I hope I can take the next year and figure that out. So truly, what I have coming up right now is bombing. Bombing and producing a good show.
MR: Any goals for 2025 in terms of comedy?
RN: I suppose I should start posting clips of my material. Unfortunately, TikTok and Instagram reels are the greatest indicator of your value to the industry. Isn’t that weird? You’d think it would be about being funny to a live audience. So I’m not sure if that’s a goal as much as it is a sad necessity. The real goal is to start touring, and likes, follows, and views is what gets you booked on the road these days. Granted, I have gotten to do a lot of festivals, but most of those pay like shit—as in they don’t. So I’m hoping to have made enough connections where I can travel and at least break even on a weekend.
MR: Is there anything else you’d like to say?
RN: Please keep supporting local, independent comedy wherever it exists. Shoutout to The Laughing Tap in Walker’s Point. Shoutout to Milwaukey To The City run by Sam Barone. Shoutout to John Berens and Brandon Wein who book amazing local shows. The people in your community are cool and doing cool stuff. Spend your money on their creativity. Also come to the open mic I run with the hilarious Luise Noé at Bremen Cafe. It’s every Monday at 8 p.m. And we mean every Monday.