This the number one rule for your set: in order to joke live, gotta learn to live with regret. That’s a paraphrased Jay-Z lyric if you didn’t know. As myself, I don’t really have a lot overarching advice on live performance. I’ve done it a handful of times now, but it still feels new to me. And that may be why I still like doing it, and why I don’t want to do it all the time.
I wasn’t a theater kid, but being a film/sketch comedy kid is not far off. I have been performing in front of a camera since around my tenth birthday. It wasn’t until a decade later that I started taking improv classes in New York at the UCB theater. I knew the name UCB from podcasts and articles about all my favorite comedy personalities (I was listening to a lot of Comedy Bang! Bang! at the time). Enrolling in 101 seemed like it would be the beginning of something. While I met some cool people there, I didn’t love the pedagogy as much as I’d expected to. Even referring to it in those terms feels overly serious. The problem was they were providing roadmaps for doing comedy their way, and it wasn’t coming to me as naturally as I’d hoped. It was a deflating experience. Because I connected with that humor elsewhere, I thought I may be able find a shortcut to belonging. And maybe I could’ve, if I weren’t so stubborn.
But I wanted to do things my way, and my college was made to suffer for it. Being overconfident and having the proper connections, I was master of ceremonies for a number of events at my school. I wrote material suited for my campus audience with a lot of school-specific references. A friend of a friend at the time referred to me as “the guy who didn’t understand how to do stand-up,” a comment I definitely never thought about again until just now.
At the same time, my mom was beginning her own journey in live comedy. After seeing a mediocre brunch comedian in NYC, she was in-spite-ered to express some of her own thoughts mirthfully. For months she would come to my improv shows to support me (thank you), but also to report her progress crafting sets on the page. Even though she’s my mom and I owe her everything, I still needed her to back up that talk. Talkin’ ain’t doin’! I activated my college connects once again to book a space on campus, invited a ton of friends and we put on a show together on Mother’s Day weekend 2019. It was extremely fun.
I don’t remember thinking much about live comedy after that. I had multiple jobs, a thesis to write in order to graduate and, most importantly, a web series I was producing. I was a busy little bee right up to lockdown, a time that I thought about live comedy even less. It wasn’t until the vaccines were out, the listed house I was living in was about to sell and I had decided to move to Chicago that the subject resurfaced. Knowing exactly two people in my prospective city, I found a temporary living space around the corner from the Annoyance theater and began improv classes my first week living in Chicago.
Annoyance was a more positive experience for me than UCB. No one was being asked to fit a mold, just to be a conscious and prepared version of themselves. I met even more great people there, but it has not become my home either. I don’t think my home is on a stage at all. And I feel that way because I can compare it to how I feel behind a camera working with actors. That’s home.
Still, over the years I’ve had the opportunity to do lots of different types of comedy onstage, and I’ve loved every minute of it. The community has been very gracious to me and my status as a perpetual tourist. Chicago rules because, despite it being a chief export, the city isn’t overly serious about comedy. I’ve encountered no gatekeeping and inversely have been invited on some wonderful shows. If you’re reading this and had a hand in producing any of those shows, thank you.
In 2022 I shot a pilot for a dine-in pizza-based comedy interview show. The hook of the episode was at the end of my meal I’d stand up at my table and start telling jokes that I’d written since sitting down. When I pitched this to Pizza Lobo, they requested that I instead program an entire evening of comedy for their patrons. I said sure, even though it was a lot more work than my initial idea. I bring this up to say that was my second time producing a comedy show. The third was Mother-Son Stand-Up II in spring 2024. Friend Andrew allowed us to use his studio space in Ravenswood for the performance. Because my mom, who still lives in New York, and I had done some reps by this point, we decided we were ready to split an hour.
I’ve said this on here before, but one of the perks of not getting onstage very often is that I’m able to sweat out a new set each time. Writing half an hour meant I had to be looser, less punchy. Where my other sets were hoisted by hard jokes, here I’d have to show more of my personality. It pushed me to write about things that I normally wouldn’t. For example, I did a whole section on being biracial, which I felt good about addressing because instead of using it to get a quick “white guilt laugh” (which are valid I suppose), I could explore the topic more. I wrote as I normally do, stream of consciousness followed by some tightening. I’m not meticulous whatsoever. In movies, I have multiple chances to get something right, and I’m harder on myself when ideas don’t come across. Live situations I put less pressure on myself – though I’d be lying if I said pressure didn’t always find me. But when the time came, the thirty minutes went by fast, to the point I was sure I’d left out some material. Friend Mary assured me, “No, you were up there for a while!” I can’t speak to my mom’s process, but she also held the room for about 25 minutes, and the crowd loved her. That audience was phenomenal. It wound up pouring rain that night, but thanks to some close friends and Andrew’s promotion we managed to fill up the chairs I’d borrowed from my job and jammed into my roommate’s car. Rudy Castillo opened up for us. Rudy and I worked at a restaurant together and I had yet to make good on a promise that I’d help him get on stage for the first time. He seemed a little too good that night to have never done it, but you’d have to ask him about that.
Here’s a clip of our post-set Q&A.
My mom told me this August she wanted to come visit in the fall, and that she wouldn’t hate if I organized something. I didn’t have a good enough reason not to.
This time we were at the famous Bughouse, which meant I had to bug everyone that the show was happening so we’d have an audience and my mom didn’t think I was a friendless weirdo. The Chicago people who came out to the show are the realest there is. The aforementioned Mary McKenna opened up, after a sketch where I portrayed my own grandfather disparaging the comedic arts. This was the first time I followed my mom in the order, who told a wild story from her waitressing days. I did my second half hour, and me and the people who saw both thought it was better than last year’s. I was psyched to hear that, mostly because I had more ownership/responsibility over this show than any previous outing. More than any other time, it was important to me that people enjoyed themselves. That comes with more stress, but also a greater payoff.
Here are some highlights.
If you missed Mother-Son in Chicago, you may be out of luck. If there were to be another team-up, I’d like for it to be on my mom’s turf. See how I fare with a Catskill crowd. I have some other plans for 2026, which I’ll get into more in the next edition.