Stand-Up Outside, On A Sidewalk
A Live Clip + Show Note 5
Comedy can take you to some wild places. Many comedians dream of standing on the stage at SNL, filling an arena, packing seats at a theater, or headlining the hottest club in town. Most cut their teeth, however, in bars, breweries, or cafes. But doing comedy outside? On a sidewalk? In front of a pizzeria? That was my experience last night, and it was, well…different.
You’re standing on a sidewalk next to a busy main road, mic in hand, trying to make people laugh while the world carries on around you. It’s not the semi-quiet setting of a club or even the somewhat noise venue of a bar & grille—it’s loud. It’s raw. It’s super gritty. It’s real life. Passersby of all sorts came through, too. At one point, a homeless man with cardboard slippers and a net for a shirt strolled right past the “stage.” At another, a motorcycle club roared by, drowning out everything with their engines.
Some people stopped to see what was happening, then moved on. Others didn’t even glance in our direction. One guy was so uncomfortable walking through the middle of it all that he stepped into traffic to avoid us entirely. Umm…that’s next level stuff right there! This wasn’t your typical venue in any sense of the word. It wasn’t even close. This was not a place where carefully crafted, tightly written jokes shine. I learned that quickly. I started with some of my written material, polished material—my preferred style—and got next to nothing. Sure, a few laughs trickled in here and there, but the noise, the chaos, and, let’s be honest, the self-induced chemically dulled faculties of the audience didn’t help.
But then something shifted. I leaned into crowd work, even if only for a minute, ditching the script and engaging directly with whoever was there. That’s when I got the best laughs of the night. Here’s a super brief clip of one such interaction.
Just like the setting, it wasn’t polished at all, but it was fun. It was the kind of laughter that happens when you connect with people in the moment, not through a carefully constructed setup and punchline, but by riffing on who or what’s right in front of you. A major takeaway: comedy often works best when it matches the venue.
I plan to do this venue again, but next time, I’m leaving all “written material” at home. This is a place for storytelling, ranting, and just talking with people. Formal jokes can wait for the clubs; this is about going with the flow. I love the craft of writing jokes and the satisfaction of delivering them well, but the more informal side of comedy—crowd work, improvisation—is something I’m still growing into. I’m enthralled by it, and despite my many years speaking in the pulpit, in lecture halls and classrooms, and at academic conferences, it’s still a challenge. The only way to get better, though, is to practice, and I think a venue like this is the perfect place to do just that. What I needed to do was treat it like the lunch table from 6th-12th grade, that place where we all joke and mess with each other and get incredible laughs.
Right after my time on the mic, the host said something that stuck with me: “If you can make people laugh here, you can make them laugh in any club.” I think he’s right to a degree, at least when it comes to crowd work and the kind of spontaneous comedy that this venue demands. Last night, I had 15 minutes on the mic but tapped out before 8. I regret that. I let the unfamiliarity of the setting get to me, and I’m determined not to let that happen again.
Comedy is a balance of being a student, a practitioner, and even a teacher. Last night, I learned that comedy doesn’t always need to be polished or perfect. Sometimes, it’s messy, loud, and unpredictable, and that’s okay. I learned that stepping outside my comfort zone, even if it’s awkward or uncomfortable, is necessary if I want to grow.
I’m already looking forward to the next sidewalk set. It’s a challenge, no doubt, but if I can find a way to make it conversational, to really connect with people in that chaotic space, it’ll be a huge step forward. And maybe next time, I’ll stick it out for the full 15 minutes. That’s the beauty of comedy—it’s always a work in progress. And sometimes, the progress happens in the most unexpected places, like on a sidewalk in front of a pizzeria next to a noisy street.
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