Reflections on Comedy and Me, After Recording My First Standup Special
With the first of my big projects for 2025 in the bag, taking a moment to wax nostalgic.
This past weekend, we filmed my first standup comedy special at Mad Swede Brewing in Boise, ID. I did back-to-back shows at 7:00 PM and 9:00 PM, and wrote a comedy sketch to open the special, which we filmed that afternoon. It will still be a little while before the special is released (no firm date yet), but as the final performances of the act I built over the last four years are fresh in my memory, I find myself in a reflective mood, so I wrote this (very) long post taking a walk through the past, retracing the steps of how I got here. If you’re not interested in my life story and just want to know how the damn shows went, feel free to scroll to the subheading “The Big Night” toward the end of this enormous post.
How Did It Start?
Some 22 years ago, when I was 14 years old, my dad took me to see George Carlin. As we stood in line with our tickets, my dad said to my brother and me, “You guys will probably remember this for the rest of your lives, because as far as I’m concerned, it’s like getting to see Elvis live.”
It wasn’t just my first live comedy show. It was my first concert. To this day, when people ask about my first concert, it’s the answer I give. Yes, I know people usually mean music, but screw that. No music concert I’ve ever been to sticks out in my memory like that one. It was like seeing Elvis. And if I’d been the right age to see Elvis when I was 14, maybe today I’d play rock and roll.
But I didn’t. I saw George Carlin.
He read us “Modern Man” from a few sheets of paper because he didn’t have it memorized yet. He told us he was going to use it to open his next special. I loved it, and was thrilled that I was among the first to hear it. By the time the special finally came out, I’d been dying to hear it again for about two years.
Near the beginning of the show, someone screamed, “I love you!” and a smirking Carlin replied, “I appreciate the enthusiasm, but individuality is not a good idea tonight.” Having heard a particular vulgar recording of Carlin going off on a heckler (pure gold to the ears of a teenage boy), I found myself hoping I’d witness something similar in person. It didn’t happen, but that was fine. A minute later it was forgotten, I was so swept up in the performance, alternating between laughter and awe.
I was familiar with his work. I’d seen his specials. I even had one of his books, which I took to school and read aloud to my classmates (when there were no teachers in earshot, of course), but in person, there was magic in that room.
I was already writing short stories constantly and attempting the occasional novel (I was still eight years from seeing one through to completion). I loved words and wordplay, and would memorize poems and movie monologues for fun. I was a theater kid and I made home movies with my siblings. I put jokes in my school presentations to get laughs out of my classmates. I understood all the elements of what he was doing. But damn was he good. It was no wonder there were hundreds of us (almost all of them adults, aside from my brother and me) paying good money to watch him do his thing.
When it ended, he took a quick bow, then ran—literally ran—off the stage and out the door. As we exited the building, my dad said, “How ‘bout that. And tomorrow he’s in another city, doing it again.” As a thousand people filed out of the building, all laughing and repeating their favorite jokes, I remember thinking, “What a way to make a living!”
Later that year, I wrote five minutes of jokes about my math teacher and how much his class sucked, and signed up for a bi-weekly talent show held in my school library which students mostly used to share poems they’d written. I walked to the front of the room, swallowing my stage fright, and did standup for the first time.
Obviously the material wasn’t great, but I went to a tiny high school where the graduating classes numbered in the 30s. Not only had the 15 or 20 people in that library all experienced Mr. Ramsay’s math class, but Ramsay himself was standing right there. In that room, with that audience, that set killed. Even Ramsay laughed. His class was hell, but he had a sense of humor. Still, mocking an authority figure in front of the very people over whom he holds authority—that’s a staple of comedy if ever there was one.
That was the spark. Two decades later, the feeling is the same.
(below: audio excerpt from my first standup set, at age 14, about Ramsay’s math class)
The Covid Boost
I didn’t stick with standup comedy. I wrote funny things frequently, but actual standup came and went for the next 18 years. I would get into it for a month or two or three, then I would get frustrated, usually about how hard it was to get stage time in whatever city I lived in at the time, and standup would fall by the wayside for months or years as I immersed myself in a writing or film project. I started posting my jokes on Facebook instead, checking my phone for notifications all day to see who else might have chuckled at my thoughts. I bullshat myself that it was a substitute for performing.
When the Covid lockdowns started, I hadn’t done a set in six years. But something about being stuck at home made me realize I’d been spending too much time at home in the first place. I promised myself that when the world reopened, I would stop posting my jokes to social media, and go tell them to drunk people in person instead. I found myself back in Boise when the world reopened (another long story), and began searching the internet for local open mics, crossing my fingers there was something resembling a standup scene here. I found two open mics—one at each location of a brewery called Mad Swede.
I’d always been shy, but years of social media addiction coupled with moving from city to city and not knowing anyone had made me increasingly socially anxious. I wasn’t really thinking about comedy as a career pursuit. I just thought getting on stage and talking shit would help alleviate some anxiety and maybe accelerate building up a new friend group. I sat in on two open mics, one at each location, and asked myself, “If I went up there tonight, would I be the worst one here?” I felt like my ego could take being second-worst, but I didn’t want to be the worst. If people drove home saying, “Why the hell did that one guy sign up?” I wanted them to be talking about somebody else. If the other person in the car said, “Yeah, and that tall guy wasn’t very good either,” that would be fine. I could be the afterthought, just not the thought.
After two shows, I said, “There’s no way I can be the best, but dammit, I’m pretty sure I can be funnier than somebody.”
So on May 24, 2021, after almost seven years, I got back on stage.
Mad Swede and Blue City
I made myself a goal. One hour. The sets at open mics are short—usually about five minutes. Sometimes three, sometimes seven, but rarely any longer. Every time I did a set, I wrote down how many minutes I’d done and added it to my total. I told myself, “If you get to 60 minutes and you hate it, you can decide this isn’t for you anymore. But if you get to 30 and you’ve bombed a couple times and you’re dreading going back, you still don’t get to give up until you done your 60. No quitting until you’ve given it a fair shake.”
The first one, I did okay. The second one, I killed. The third one, to this day, is probably the worst set I’ve ever had. I drove home going, “Damn. If I hadn’t promised myself an hour, it’d be hard to show my face there again.” But I made the promise, and I kept it. I also knew it was the perfect thing to have happen in the first three sets. I’d done enough standup to have had good sets and bad sets before, but now the whole spectrum was fresh in my memory. “Here’s how it feels to have an average set. Here’s how it feels to destroy. Here’s how it feels to eat shit. That’s the life. Take it or leave it.” I decided to take it.
Most of my past sets were at a comedy club in Austin, TX where 50 comics applied to be on the list each week and only 20 got picked. You were lucky if you made it on stage twice a month. I thought it might take me six months to get my 60 minutes in, but it didn’t. In Boise, I got on stage every time I wanted to, and before long, other comics told me about open mics I’d missed in my online searches. After only a month, I was already about to hit my goal of 60 minutes.
In those days, the open mics at Mad Swede were produced by Blue City Comedy, run by a producer and comic named Hailee Lenhart-Wees. A few weeks into performing, after one of my better sets, she asked if I wanted to take part in a competition she was holding called “Comic of the Month” where five local comics competed for the title, as well as a $100 cash prize. A runner-up would also get $20.
I was the runner up.
That was the show that put me over 60 minutes. It was also the first time I ever got paid to do standup comedy.
Climbing the Ladder
Most of my comedy firsts came from Hailee—my first payment, my first time guesting on a show, my first hosting gig, my first time as a feature act. Often she had to push me. I wasn’t even sure I was trying to “be a comic”. I was already trying to be a novelist and a screenwriter and didn’t really need another pursuit. I was just trying to be social and working out some anxiety.
So she would ask me to do 25 minutes to open for someone, and I would go, “Oh, I don’t know if I could do 25 minutes…” And she would go, “Shut the fuck up. I’ve heard you do 40 minute of different shit at open mics. Just put a bunch of it together,” and eventually I would relent. When it worked out, I always seemed to be more surprised than she was.
After a year, the anxiety was mostly gone. A lot of my early material was about shyness and being socially awkward, but I found myself moving away from that and into loud, animated rants that were closer to a lot of the comics I’d grown up on.
The “exposure therapy” aspect was over. But I was still doing it, because I had remembered how much I loved it.
(below: segment from a set at Mad Swede Brewing on February 17, 2023)
Nate Ford and My Graduation To Headliner
One of the longest-working comedians in Boise at that time was Nate Ford. He was a guy who a lot of us looked up to. Around the time I was talking about math class at a talent show in my high school library, he was getting his start as a working comic. He didn’t have giant gaps like I did. He’d been doing it steadily that entire time. He was funny as hell. He’d performed all over the country, opened for a dozen big names, but still wasn’t above having drinks with new comics and talking shop or just bullshitting until three in the morning.
A few months in, having drinks at someone’s house after a show, I said something to the effect of, “I’m just doing comedy because it’s fun. I’m not sure I see a future in it for myself.” And he said, “You might have one if you wanted it. I’m not gonna sit here stroking your ego, but I think you’ve got something.”
It was one of the early compliments that triggered my shift in mentality. The transition was slow, but I went from thinking, “This might be a fun, casual hobby,” to, “I wonder how far I can take this.”
I guess that transition was complete after about a year, because when Nate pulled me aside after a show around that time and said, “I’m looking for new headliners. Do you have 40 minutes?” I said yes almost before he’d finished the question. Nobody had to convince me I could do it anymore.
That show took place on October 28, 2022. Nate himself opened for me. After the show, he shook my hand, told me it was a great set, and said, “Welcome to the club.” I never graduated from college or even high school, but imagine the feeling was similar.
A few weeks later, Nate opened for Bill Burr, my favorite comic working today. After that, anytime I was hosting and it came time to introduce him, I would say, “This next guy has opened for Bill Burr, me, you know… all of the greats.” It was funny, but I was also proud. Not just of my friend for opening for a legend, but of the fact that I was two degrees of separation from my current favorite comic.
A few months later, I won Blue City’s “Comic of the Year” competition, then headlined at Mad Swede, a bunch of other local places, some other cities, and a couple of neighboring states. I spent two years hosting a weekly open mic and averaging a show per weekend. I stayed busy, getting all my material just the way I wanted it.
Burning Out and Burning Jokes
But I started getting sick of the hour. A joke is exciting to try out the first time, and it’s fun to tinker with it the next ten or twenty times, but by the time I’ve done it fifty, sixty, seventy times, even if the joke works, the creative thrill isn’t really there anymore. It’s also rare that a brand new bit will work as well as a bit that’s been polished over the course of fifty shows. And even if I write a new bit and take the time to really get it working, my hour has been reaching a point where it hurts to rotate stuff out, because everything that’s in there has been working really well.
Also, I rarely post material on social media, even though people are always telling me they want me to. Like a lot of comics, probably the majority, I don’t like having a joke available online if it’s a joke that I’m still doing on stage. A version of it that is available for the whole world to watch for free anytime they want feels “final”. Once it exists in that form, I don’t want to do it for an audience that paid money to come see me. That’s why, when you tell a joke in a format where it’s now publicly available, a lot of comics call it “burning” a joke.
So the problems were as follows:
I was tired of my hour, even though it was still getting big laughs.
It was hard to make myself favor new bits when old ones still worked well.
I had minimal online content because I didn’t want to “burn” it.
I’m still probably a long way from a streaming service coming to me and asking for a special. I don’t even an agent or a manager and I’ve hardly gone on the road. But I thought, well, I can probably solve this problem for myself. Just do it one more time, get good footage, and send it out there, like you’d do if you were a pro. Take that whole hour away from yourself, let it live forever for whoever wants it, and force yourself to go back to the blank page. Burn it all.
I believe it will have a different title when we release the actual special, because I wrote an opening sketch that sets it up differently. But for the live show, that’s the title I used: Burn It All.
Planning a Special
Late last year, Mad Swede told me it had been a while since I headlined and asked if I wanted to do another show for them in early 2025. I told them yes, but only if I could do two shows back-to-back, and I was going to bring in a film crew. Mad Swede and I have had a great relationship over the last few years, and they were quick to say yes. I was glad. Mad Swede has been my home base while I have built this hour, and most of the material was performed for the first time on that very stage. There could be no place more perfect for my first special.
As for the footage, in 2024 I had sent a short screenplay to a local competition, and a filmmaker named Brandon Freeman had directed it, through his company Flying Fedora Film. Our movie, Let’s Get Lunch, had won Best Film in that competition. By coincidence or kismet, the same week I made the deal with Mad Swede about doing the show, I saw a post from Brandon putting it out “into the ether” that he hoped to shoot a standup special in 2025. I approached him immediately.
I also approached Hailee, who pushed me early on, and asked her to host for me. If Nate Ford hadn’t moved away last year, I sure as hell would have approached him too.
Everything felt full-circle. Like I was arriving at something I’d been on my way to for years without knowing it.
For the last three months, the plans for this show have occupied almost all of my creative energy. I have been creating and printing advertisements, I have been hitting every comedy event I can, telling everyone to come out, I have been working it into conversations with Uber passengers and passing them print advertisements, I have been messaging old friends. I have rarely shut the hell up about it.
I have been typing up material, combing through it joke-by-joke to avoid leaving behind any potential laugh I have been missing in this material. I’ve been performing it in pieces at every show and open mic I could get to, trying to make sure it’s perfect. I have been working as hard as I have worked on anything, trying to make these two shows into everything they can be.
The Big Night
Boise comedy audiences like to make me sweat. For some reason, it’s impossible to get the bastards to plan anything more than a couple days in advance. Despite promoting my ass off, as the week of the show arrived, we’d sold less than a third of the tickets for the first show and almost nothing for the second. I had been hoping I could sell them both out in advance and save myself the stress of wondering if I’d have an audience, at least taking one piece of stress off my shoulders, but it didn’t happen. The day of the show, I was pacing for hours.
It took until the last minute, but sure enough, we sold out the first show.
I told myself, “Just in case no one shows up for the second one, nail it now. Make this first show so good you don’t even need the footage from the second one.”
A couple times early on, I got too inside my own head and stuttered over jokes, but it was nothing major. The biggest mistake I made was completely forgetting to do a five-minute bit that had been part of my set list, but other than that, it was one of the best sets I’ve had. Great crowd, great energy in the room, and a ton of fun had by all.
I left the stage exhausted, as I always am at the end of a show as headliner. I guzzled a couple glasses of water and took some deep breaths. I’d headlined plenty, but this was my first time doing it twice in one night.
I shook hands with the first audience on their way out and greeted friends in the second audience on their way in. I made my notes about the forgotten bit I needed to make sure to remember in the second set and the little things I stuttered on that I hoped to get through more smoothly. My heart rate finally slowed to something resembling normal.
A bittersweet feeling finally hit me—one of those thoughts you’ve been aware of intellectually for a long time but haven’t really felt in your heart yet. It was a feeling that said: I have been telling these jokes for years. In a few minutes I will tell them again, and it will probably be the last time I tell most of them.
A lot of my comic friends came to the second show and hung out beforehand. I told them it was a weird feeling to know it was the end of the road for this material, and they said, “Yeah, make sure you have fun out there. Savor it.”
I tried to, but I’m not good at that. When I’m in performance mode, it’s like I’m a different person. Stage Greg has little use for what Real Greg is thinking or feeling, in fact he finds it distracting. Stage Greg has a show to do, and he doesn’t have time for anyone else’s shit—least of all Real Greg’s. I guess I had fun. Or at least it was fun when I left the stage and reverted to Real Greg. But mostly, what happens on stage exists in a parallel world, to be recalled later only through a dreamlike fog, the way a werewolf’s rampage on the night of a full moon is remembered by the blood-drenched human he wakes up as the next morning.
We didn’t sell out the second show, but we got close. They were big laughers. Though as I watched a woman in the front row drunkenly interrupt the feature act multiple times, I got a sick feeling. Not one of these people. Not tonight.
Before bringing me up, Hailee reminded everyone that we were filming and asked people not to interrupt during my set, but the woman had gone out to smoke at that moment. I hoped the other people at her table would rein her in if she started doing it again. But they were drunk too, making out and only half-listening. They were clearly going to be a problem table.
Mercifully, she had not returned to the room when I did the five-minute bit I had forgotten the first time around. It killed. I thought, Okay. We probably have the whole special in camera now. The first show was great and we got the one thing I forgot.
But aside from the one table, the second audience was amazing. I was getting some of the biggest laughs I’d ever gotten. So when the drunk woman returned and started trying to contribute again, I got annoyed. Even though we had great footage, she was messing up potentially even better footage.
Most of the time I’m nice to hecklers. At a normal show, if one joke gets derailed, it’s no big deal. I’ll tell it again at the next show, and in the meantime, maybe I can milk something funny out of what’s happening in the room. At this show, no, this was the version of these jokes that would live forever, and a drunk idiot stepping on my punchlines was doing real damage. So with her, I wasn’t nice.
I managed to tell her to shut the fuck up in a way that was funny. Not so much to her or the people at her table, but to everyone else in the room. I know because I got an applause break and a half dozen compliments on that specific moment after the show. I also told her to shut fuck up in a less funny way a few minutes later, and Hailee told her she was one comment away from being kicked out, which seemed to finally shut her up.
I probably won’t use the footage of the more serious “shut the fuck up” moment because it wasn’t very funny. I almost certainly will use the footage of the funny “shut the fuck up” moment. Looking back, if I had it to do over, I could have blended the two together into a meaner version that would have still been funny, but I suspect what we ended up with is still good. It may not be as mean as I was hoping George Carlin would be with that potential heckler at the show I saw when I was 14, but if 14-year-old me could have seen his 36-year-old self interacting with this heckler, I think he’d be proud.
And at the end of the day, even though she messed up a joke or two, that’s why we filmed two shows. Between the two them, I’m sure we have a working version of everything, and I have no doubt it can be compiled into a special I will be proud of.
The Comedown
Performance is a drug—as all comics, actors, and musicians know. The bigger the show and the better it goes, the longer it takes to come back to Earth. And these were two of the best shows I’ve had, not to mention the culmination of three months of hard work, or four years depending on how you look at it.
Afterward, there was an open mic at Mad Swede, and I hung around and chatted with the other comics. I hadn’t planned on doing a set, but another comic told me he always thought it was important to do an open mic as soon as possible after a big show to humble yourself. I decided that was fair enough, and I did a quick set for the eight or so people in the crowd at 1:00 AM, using material I hadn’t put in the special. It went fine. And as great as a huge show feels, “fine” isn’t bad either.
I have two shows booked later this month, telling jokes on a trolley for a comedy bar crawl. I’ll probably have to use a few of these jokes a couple more times on those shows. I probably won’t have enough new material by this weekend to phase it out completely just yet. But very quickly, that’s the plan.
I’ve got pages and pages of premises, and a couple of half-decent bits I didn’t put in the special that might work well with some spit-shine on them. I’m not sure if I’ll start hitting the open mics with new material right away or if I’ll rest for a few weeks. I’m kind of playing it by ear, seeing how I feel.
Plus, I have a lot of work to do editing the special.
There’s a lot I don’t know yet. I don’t know for sure when the special will come out, but later this year seems likely. I don’t know for sure where it will be, but my YouTube channel seems likely.
I also don’t know what material I’ll be doing in my live shows by then, but I’d like to think I’ll be well on my way to a brand new hour.
I've been hoping you would put a video special together--your work seemed like it had reached the point where it would give you a boost.