Comedian Brooks Wheelan talks Midwest touring, travel writing ahead of KC dates

Brooks Wheelan is a seasoned veteran in the comedy world, from being on SNL for a season to opening for John Oliver and Seth Meyers across the country (Wheelan returns to KC with Meyers in April). His latest special, Alive in Alaska, not only offers an hour of relatable Midwest charm but also chronicles his 2-week tour to the corners of the last frontier state. Now, Wheelan is in the middle of his most recent comedy tour, stopping at KC Comedy Club this upcoming weekend.

Brooks Wheelan chatted with us ahead of his February 5-7 shows at the KC Comedy Club. He reflects on living in Kansas City, his passion for traveling, and what people can expectfrom Midwest comedy.

The Pitch: You lived in Kansas City early in your career. How was your experience here?

Brooks Wheelan: I was coming from Iowa. It was the first time I’d ever legitimately been to a place that was a ‘real’ city. A city with an actual scene and guys my age pursuing comedy. I was only twenty when I lived in Kansas City. I remember I had to borrow someone’s ID to see Wolfmother at the casino there. I was so young I couldn’t get in most places.

Courtesy of Brooks Wheelan

I moved to Kansas City when I was twenty. It was really the first time I met guys my age who were as passionate about comedy as I was. I’m still friends with a lot of them today, and they’re all great dudes – they were so funny. Being in Kansas City was exciting for me because it was the first time I realized comedy could be a totally possible job. 

I did comedy at the brand-new Stanford and Sons, and the Improv had just opened. I remember seeing Tom Segura open for Steve Byrne there, and he just blew me away. Turns out my taste was right. There were some really fun open mics, especially at The Brick. I remember some real nutsos in the KC comedy scene. They’re the big dogs because they’ve been doing it for ten years. So you have to respect these absolute psychopaths. It was great.

Your Midwest roots influence much of your comedy. Do the stories growing up in Iowa always translate to, let’s say, the audience in Los Angeles?

I always do the same set everywhere. To me, that means it’s a really good joke, you know what I mean? I’ll open for John Oliver at the MET and Philly for this New Year’s show; then two days later, I was in Janesville, Wisconsin, doing the same set at a tiny comedy club. If these jokes work in front of John Oliver’s fans, who are seeing a show at the MET, and these people in Janesville, then that’s a good joke. If you believe what you’re writing, you shouldn’t have to cater to audiences.

But I revere the Midwest. I love it; it is the most overlooked part of the country. I’m partial; I spent twenty-two years of my life there. Every TV show I’m writing on, or anything I pitch, takes place in Iowa. It’s just a part of the country that is overlooked, with how genuinely funny it is. Respectfully, it’s just a wild place.

I honestly love performing in the Midwest. Everybody gets every reference, and it really is like hitting off a tee ball because they relate. If you know what a garage refrigerator is, you’re going to like my comedy.

Can you share anything you are working on now?

Yeah. So I had an idea about a show where everybody dies at the end, and I thought that was pretty interesting. Basically, I had a dream where Ross committed suicide in the pilot of Friends, and I was like, what would that show look like? 

I wanted to talk about your podcast, Entry Level. It’s been going on since 2017 and focuses on comedians’ first jobs. How has the podcast’s scope changed over the last 8 years? 

The podcast started because I was an engineer and spent all day not wanting to be an engineer. I was like, let’s have a job where I interview people about all the jobs that they used to have for people who are like me – in a job that they don’t want, with aspirations to do something else. It was great and rocking… And then Covid happened. I hated Zoom interviews and started asking myself, ‘Why am I doing this?’ I don’t even care about this. I still do the podcast, but only when I find somebody I really want to talk to.

You are an avid blogger, documenting your extensive backpacking and travel experience around the world with comedy. What made you start posting about travel, and are there any larger aspirations there?

The aspiration is to write a book about comedy and travel, and Substack seemed like a really great way to figure out how to do that. I really enjoy Kitchen Confidential by Anthony Bourdain. I want to do that for comedy. You know? I’ve done every part of comedy, and I might as well write about the inner workings of comedy in other places. Not like a tell-all by any means, but writing in a way that is interesting for people.

Coming up, I’m going to Alaska for my fortieth to be dropped off by a boat and camp on an island for a while. It’s a beginner backpacking trip with an open invitation to all my friends. I’m like, yo, if you guys want to go to Alaska and camp on an island, I got it all set up. I spent my thirtieth in Alaska camping, and I’m like, let’s do that for all the zeros.

You’ve written some of my favorites in recent sketch comedy in Almost Friday’s Edward 40 Hands, and I Think You Should Leave’s Little Buff Boys (S2E1). Do you still write skits, or is your comedy focus on standup?

I brought the Edward 40 Hands idea to the guys at Almost Friday. I think my pitch was like something really bad:  As soon as you put Edward forty hands on, you find out something horrible happened, like you find out your grandma died. Those guys are really good and completely heightened the sketch.

For Little Buff Boys, we originally shot that at SNL, but it got cut for time. I was really annoyed. But overall, I got burnt out on sketch writing at SNL. That place made me believe that I was really bad at writing sketches, which will mess with you. But I still have a lot of love for that show. I just went last week to see Geese perform. 

Eventually, I found out I really like stand-up. The only time I think about sketch writing, I occasionally toss ideas around with people who are still working on TV shows, but that’s about it.

Excited to see you at the KC Comedy Club February 5-7. Any last thoughts?

Check out Alive in Alaska on Youtube. And if you dig that, see this new junk. I’m really proud of this new hour I have. I’m about ready to shoot a new special, and I am planning to do it in Iowa, since it’s home. I usually get annoyed when people shoot specials in their home city because it’s too easy, but that’s why I went to Alaska. I made it as hard as I could, and after that, I was like, you know what? I get to do one in Iowa next time. So see this show before I shoot it.

Interview gently edited for content and clarity.

Grab tickets to see Brooks Wheelan February 5-7 at the KC Comedy Club.