For many people involved in Milwaukee’s comedy scene, stand-up is a hobby and a fun outlet to help meet people while staying creatively fulfilled. As an aspiring comic improves, their opportunities to perform grow and their name appears on more show flyers and YouTube videos, the chances of having their second life discovered by coworkers increase exponentially.

Milwaukee comedian Carter Deems has to deal with that two-fold. Less than a year into comedy, he’s quickly becoming a regular on local showcases. Oh yeah, and he’s also an internationally-recognized name in battle rap. Using his penchant for wordplay and self-deprecation, Deems routinely disarms some of the most imposing battlers in the country with humorous bars that have been heard by hundreds of thousands of people.

Before he heads to Canada and Australia to compete in battles this spring, Deems will display his other skill Thursday night during a Sugar Maple stand-up showcase. Milwaukee Record recently met up with Deems to talk about his origin in both comedy and battle rap, how one art form informs the other, and why he’s a sucker for puns.

Milwaukee Record: Were you involved in stand-up before you moved here or was it something you picked up in Milwaukee?

Carter Deems: No, I’d never done it before. I started almost a year ago.

MR: So you were new to a city, new to a stand-up scene, and stand-up in general. What has the adjustment to all those changes been like?

CD: I moved here and didn’t know anyone at all. When I started stand-up, it was almost as a thing to get outside the house and meet people. I’ve always written jokes, but never brought them on stage outside of a rap battle. I saw Karma had an open mic and that was near my house, so I went to check it out. I went and watched three or four times before I tried it. I did it, and the first night, a ton of people came up to me and were very encouraging. I’ve met some of my best friends through the scene, and it’s been nothing but welcoming. Everyone has been really encouraging.

MR: You mentioned rap battles. Your rap battles are seen by tens or even hundreds of thousands of people online. When did that start and what brought you to that world?

CD: I made the mistake of my battle rap name being my real name because it makes it searchable by my employers. I’ve been doing it for about eight years now, back when I was in college. I’d always been into rap music, and I just went one night with a friend to an underground rap battle. I went an watched a couple times and decided to go up on stage and try it out. I got destroyed and it was the worst night of my life. I hated that feeling, but I wanted to at least get to a point where I didn’t embarrass myself.

MR: It seems like you disarm a lot of your opponents because you inject a lot of humor and you make fun of yourself, so you’re set them back by having a lighthearted and self-deprecating approach.

CD: I mean, I definitely have somewhat of a character when I’m doing battle rap or even in stand-up too, but it’s not like I sit down and try to draw up this person that isn’t me. It’s more of a magnified version of who I am. I’m not a tough guy. I’m not intimidating and, you know, I face these guys that talk about shooting me or shooting my parents. On stage or in the ring, I feel like it’s an extension of who I am. That’s how I go into the situation, but trying to disarm the other person by using kindness and jokes.

MR: Do you find that one outlet kind of informs the other? Like has there been something you said in the spur of the moment in a rap battle that you were able to massage into a joke on stage or maybe a bit that you have in your act that you’ve adapted into a bar or something?

CD: Definitely. In my stand-up, I’d say probably half my jokes extend from rap battles. A lot of them are actual lines I’ve used in rap battles or lines I’ve turned into jokes. So I’ve only been doing stand-up for a year, but I have a head start because I’ve been doing comedy in some form. I have eight years of material to turn into jokes. And my comedy style is very wordplay-heavy. I rely on homophones and metaphors, synonyms, similes, and I have some palindromes in there. I just love words and that’s kind of combining these different art forms.

MR: It seems like your stand-up has a lot of one-liners and a ton of puns. Over the course of a 15-minute set, we’re talking like 50 jokes. Like beginning from nothing at a rap battle, is tough to pull a bunch of unrelated thoughts and premises together for one performance?

CD: It is tough using one-liners, which I’ve been experimenting with some longer jokes, but that kind of my favorite. Steven Wright, Mitch Hedberg, Demetri Martin have always been my favorite comedians to watch, and I do like that kind of rhythm. Kind of like a rap battle, once I get in that rhythm with one-liners, it’s a pattern that kind of flows out. I respect the guys that can do the longer narrative stuff. I’m trying to, but it’s really tough for me to write a longer-form joke. I blame that on the battle rap because in rap you always want to hit that one-two punch then go on to the next subject. I’m trying to step out of that comfort zone more and more, but I really like that style because it gets me in a rhythm.

MR: It seems like you’re nationally or internationally regarded in the world of rap battles. There are people who will or won’t watch a pay-per-view based on whether you’re involved. You’re traveling and advancing in these high-stakes competitions. Do you feel this could reach a point where you’ll have to choose between battles and comedy or will one always be able to compliment the other?

CD: I’m getting more into comedy right now, even though I have three rap battles coming up in the next two months. But I’m definitely trying to focus all my writing on comedy. I’m really enjoying getting into stand-up and learning and trying to grow more. I’m not even near the best at battle rap, but I have been doing it for eight years and I kind of want to experiment with other art forms. I feel comedy is a really good way to do that.

Carter Deems will perform at Sugar Maple on Thursday, March 9. The show begins at 8 p.m. and it costs $5.

About The Author

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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.