10 Totally Bitchin’ Years in The Comedy Trenches with Chriees

Chris Hudson
14 min readFeb 13, 2023


It’s been 10 YEARS since I started doing stand-up comedy. What a crazy ride so far. I’m pretty sure I still have at least one joke from my first year I bust out every now and then. Read on below for some snippets from a decade in the biz from your old pal Chris (aka Lil’ c-huddy):

on the set of a short film “Cuffing Season” (unreleased) — photo credit: Travis Marshall

· How It Started
· Everything’s Coming Up Chris!
· Had My Mojo Working
· The Lost Years
· The Golden Years
· Keep Movin’ On
· Just Over the Horizon (In Conclusion)

at The Cellar Door in Frederick, MD (2015)

How It Started

I started doing stand-up in late 2011 while still attending the University of Baltimore. I was never a serious fiction writer (although in college I thought I was gonna write the next great novel), and often during writing workshops my classmates would remark that I “seem to care more about fitting as many jokes as possible in than writing a good story.” During my senior year, I had convinced my college literary magazine editorial board that the magazine release party should be hosted by someone who was doing jokes and bits while bringing up the readers and then immediately volunteered myself. I wanted to write jokes and sketches to do during the release party, so I did. I pretended that our literary magazine release party was an episode of HBO’s Mr. Show that I got to work on. I wrote my jokes and sketches down on index cards and created jokes to bring up each serious poet and short story writer. I remember one intro, “Our next writer we have coming up can never tell a lie, Truth Thomas!” I also remember that particular writer not being very happy with that intro. I did a running bit where throughout the release party I was referencing a Subway sub sandwich that one of the attendees could win. The sub, in actuality, was an empty ketchup and mustard bottle wrapped up lengthwise in a Subway sandwich wrapper. I had convinced a sandwich artist at the Subway down the street from University of Baltimore to give me some empties for my “sketch,” after I had won them over with my explanation of it. The bit was that it was a fake sub. I ended up getting booed by one of my senior year literature professors. I went to a proper stand-up comedy open mic shortly after the night of that party. After that, I was off into what would be a lucrative career of collecting drink tickets. It felt magical.

one of my first paid shows at The Yellow Sign Theatre, I’m doing a bit about my acne (2012)

Everything’s Coming Up Chris!

Since I started being paid to do comedy in 2012, I’ve had good years and bad years. And those years were sometimes both creatively and financially good and bad. 2013 really felt like me getting my sea legs. I started a monthly stand-up showcase in Baltimore, Maryland and named it Everything Will Be Okay, which was named after something I had said to myself one day when I was running around Station North tweaked out and sweating from my roommate at the time’s Adderall. I ended up running that showcase a little over 7 years and it was a crash course in what Comedy (with a capital “C”) was really about. It was through that show I got to work with a lot of up-and-coming headliners, many of whom are now pretty well-known comedians with insanely big fanbases.

The perspective that gave me and getting to work with some of the funniest comedians around was my best teacher. I would say if you’re serious about doing stand-up, one of the best ways to learn everything is by running your own showcase and taking it seriously (lol). Ask comedians who you think are extremely funny to do it. I’ve talked to too many newer and even experienced showrunners while doing stand-up that don’t ask certain comics because they’re afraid they’ll say no. And that’s not a way to think. I’ve gotten to do some of the most amazing shows alongside comedians I love and insanely respect simply because I asked. And also, something about getting to work with comedians you like so much is that it sets a standard of business that you step into. You end up rising to the occasion. I had risen to several occasions like some dang artisan bread.

various posters for EWBO, with the very first one in the top left corner (I ran it 2013–Jan 2020)

Anyway, I loved EWBO and The Crown in Baltimore retains some of my all-time favorite memories as far as comedy showcases go (Top Secret, Wham City Comedy, Hot Sets, Baltimore Comedy Festival, Fresh Five, the very first Leave Your Troubles at The Door, so many more [we also did a Roast of Santa Claus that might still be my favorite roast show I’ve ever done]). It’s important to have something like that to help teach you how to navigate this “business.” Plus, you can give fellow comics quality stage time. Everybody likes a good showcase with quality stage time. It’s an easy way to make friends quickly. And friends are how you get a lot of things in Comedy. All of the best things I’ve gotten to do was because of friends. Also, make sure you don’t forget to actually promote it, too.

hosting Everything Will Be Okay at The Crown (2016) — photo credit: Travis Marshall

Had My Mojo Working

2014 was another major year for me, from settling into year two of my own (successful) stand-up showcase to my first headlining show. That’s right: two years in I headlined. That’s usually a little early for a spot like that but I was a ferocious writer who was generating material about anything I could think of, and I ended up getting booked in Newark, Delaware. It was a road headlining gig, something my baby comic mind couldn’t fathom but something I also was insanely excited about. It felt like a huge break. When I tell you I hit as many mics as I could to prepare, by golly. I drove up there from Baltimore with my girlfriend at the time and it felt like a dream. Even the trash that was blowing about right off I-95 to Newark didn’t faze me. The place I was headlining was called Mojo’s and it was across from a Ramada Inn. It was kind of a college hangout type of venue, but it had a nice stage and a neon sign I loved (I’m a huge fan of neon signs). I wrote my whole set out joke-by-joke and made sure to have enough material to fill the time. I remember having a joke about OkCuid. Online dating jokes have been around for a real long time. I also did a drinking joke about blacking out in a furniture store I am still a fan of.

headlining at Mojo’s in Newark, DE (2014)

I also remember it being one of the first times I felt free enough to be loose and riffing up top because I knew I had time to. I’ve always found the longer the set, the more a comedian can kind of relax and, sure, do material, but also not have a need to load another joke in the chamber so quickly. Look around a little, make some observations, feel the room. We’re all just hanging out. I remember it being a glorious showcase, but I’m sure if I had video (didn’t have any forethought to tape it) I’d watch it now and cringe. That’s just due to the natural progression of a comedian and an *coughs* artist. We’re usually disgusted with our early work. What really sealed the deal with me that night thought were the meals and drinks that were included with my pay. It really gave me an early taste for not only the road but the possibility of what you could do if you put enough work put into your act. You could be doing stand-up in the middle of New Jersey at a punk bar, or you could be in Newark, Delaware at Mojo’s makin’ it happen.

The Lost Years

Like I said in the first part of this self-indulgent essay, I’ve had good years and bad years. Honestly, 2015 is a bit of a blur and it wasn’t due to Comedy but more Life things that affected me personally and eventually extended to my own comedy. I got so depressed that I started getting very obsessed with western pearl snap button-up shirts. My material started getting very jokebook jokey and I just wasn’t feeling good as a person. My sets were uninspired. A lot of the other comedians and even non-comedians hanging about in the scene started referring to me as the “sad cowboy.” It definitely was a time I felt like even through the detached jokebook jokes I was performing on stage, you could peek under the veil and see I wasn’t doing well. It affected my stage confidence and stand-up at the time a lot. I remember setting up one EWBO showcase with a guest host so I could do a non-host set and get some good video. A bunch of friends and people I knew came out. I got violently heckled at one point and didn’t know how to handle it. The experience was so painful I wrote a different Medium essay about it. That’s how intense I felt. I wouldn’t count that year as a good year.

rare cellphone pic of me during my “Sad Cowboy” year (2015)

2016–2017 was me getting back on my feet: I started traveling to L.A. (after properly tending to my 2015 wounds), I got interviewed in The Baltimore Sun as an up-and-coming comedian, I got to actually go up at The Comedy Store, had multiple showcases including a stronger than ever EWBO and I hit the road again seriously whenever I could (D.C., parts of Virginia, Philadelphia, the Southern PA circuit, etc.). Those years were formative for me, especially getting out on the road more than I ever had. It really taught me a lot and helped sharpen my comedic chops. I remember going to an audition for America’s Got Talent in Richmond, VA and auditioning as a stand-up comedian. I was contacted by one of the executive producer’s assistants and asked to drive over to audition for a shot at being on national television for my stand-up. Only three of us had made it in front of the producers and the comedian who was supposed to go first said he couldn’t do his jokes until he was introduced by a host, so I pretended to be the host and brought him up. Comedy is truly something that is so funny in the way it happens; it has helped bring me out of a deep pit of despair many times. I have a lot of stupid, funny stories. That’s always been a major upside of Comedy: the fact that it brings you into strange, hilarious situations.

on stage at The Comedy Store (2017)

The Golden Years

After completely getting back on my feet in mid-2017, 2018 to early 2020 (around January) were what I’ll refer to as “The Golden Years.” They were years I was truly stepping into my own. The Baltimore, D.C. and Philly scenes were booming. I got to be a part of opening a comedy club with my friends and fellow comedians in Baltimore City proper. Shows were raining from the sky like some kind of rain that books you. I was finally writing jokes that I actually liked. Not to say there wasn’t my fair share of lessons, both personally and professionally. I learned a lot more about the nature of comedy relationships getting to feature and open for road headliners out-of-town. About how to work with headliners and really do your job of giving the audience a great show. I also learned about the business side of comedy clubs. I did my fair share of barking a dozen and a half people to see an early show wherein since you had barked them up there, you better be fucking good! It’s all part of the work, though. It’s part of the journey. 2019 was a peak good year for me. I had a fantastic regular rotation of shows I was doing, I was being cast in things again (after having been in HBO’s Veep in 2014 and 2015), I recorded my first album (which also has a companion video special) and I really started crafting a great act.

Artscape 2019 at The BIG Theater in Baltimore, Maryland

I was getting into a good groove, but I was also noticing the limitations around me. I lost the last car I owned in 2016. Having no car can completely cripple a comedian unless you live in New York City. Without a car, it was very, very difficult for me to keep a presence in D.C. or anywhere else on the circuit I was used to doing. I would do road gigs with friends who were also booked on the same show and multiple times was able to book myself on an out-of-town show and bring an opener (who had a car) with me. But schedules change, comedians shift around and sometimes, they quit. I did as many shows as I could if I could get there. I convinced people I was dating to go on a weekend with me so I could do shows. That can be a real mixed bag depending on what your relationship is like (but that’s for another essay). It really took a toll on me as someone who was raised Roman Catholic and who wouldn’t ask for water in a desert. I’ve said it a billion times before: having a car is a legit Comedy credit.

the cover for my 2019 album, photography by Travis Marshall

Keep Movin’ On

In mid-to-late February 2020, I moved to Portland, Oregon. I had done a week of showcases there in 2019 and liked the scene a lot. I still maintain it’s a strong joke writing scene and I felt like I had stayed in Baltimore / D.C. too long and wasn’t moving forward. Of course, y’all know what happened in March 2020. Right after I got here, a global pandemic hit. Nice. I’m going to admit it, I don’t count 2020 as a Comedy Year for me personally. I did a crapton of Zoom Comedy showcases and I did start a new podcast (might as well since I had the time) but that year for me as well as probably for a lot of other people was just shit. We all did what we could to get through that year with our sanity intact. And my 2021 was me (and everybody else) getting back into the swing of live comedy shows post-COVID. That was a mess: masks, hand sanitizers, sanitizing the mics, unpolished jokes about COVID, it was very messy. It was like swimming again after you hadn’t swum in over a year. And if the water you were swimming in could potentially make you sick. It was gonna take a hot minute to get your stroke back. But oh boy, was it fun getting back into stand-up. I even cherished the live shows I got to do in empty parking lots to cars that would honk their horns for our illegal nighttime outside speakeasy stand-up comedy jamboree. By the end of 2021, I felt like I was right back into the thick of it.

a less than 15 minute supercut of me getting back into stand-up in 2021

Just Over the Horizon (In Conclusion)

I’m happy to say 2022 was my best year of doing stand-up comedy yet. That’s a good thing for so many reasons. I got to do multiple shows at what I think is one of the best comedy clubs in the country (Helium Comedy Club PDX), got to go back to Baltimore and surprise close out a Baltimore Comedy Festival showcase to a packed, sold out crowd at The Lou Room Comedy Club and I restarted a showcase I had only done once which ended up being the most fun and successful shows I’ve ever done (Leave Your Troubles at The Door, check it out if you’re ever in Portland (Oregon) or if you suddenly see it’s coming to your city). That being said, I do want to make clear: this business is full of NOs and A LOT of failure. I’ve had more than my fair share of obstacles. I remember one particularly painful “no” I got was outside a comedy club one night, after years of trying, I finally got to audition for the manager of a club I so badly wanted to work. After I had a very good set, my friend and fellow comedian who already worked at the club said “So, how about Chris?” and the owner looked over at me and went “Ehhh, I don’t like his shirt.” I was wearing a plain grey sweatshirt. That was it. I wasn’t given a go ahead to even get the chance to work the club. I was devastated. The reason I’m even bringing it up is because throughout all the peaks and valleys, my worst shows and times where it felt like no one was booking me, I continued on. It seems that is what is required in almost all things if you wanna be successful.

I can say I’ve been lucky enough to hang out with and do shows with some of the best, most successful comedians and even some of my comedic heroes and they all pointed to Comedy being more of an endurance sport than anything else. You have to endure. It’s easy when it’s good and everyone loves you. But it’s harder when you’re wearing a pearl snap button-up cowboy shirt, and no one talks to you because you’re in a corner writing a joke about married peanuts discussing 9/11 (a real joke I was doing back then). We all have to continue, strive for improvement and be a better comedian and (hopefully) person than we were the day before. That’s the goal, anyway. There is no finish line. I’ve always said to myself, “If I’m not having fun, I’ll quit” but I’ve always found a way to have fun. Even when stand-up is bad it can be fun. So, since it looks like I might be doing stand-up until I die, I’ll see y’all just over the horizon. Thanks for reading. You can follow me on Instagram. I wouldn’t be a good comedian if I wasn’t plugging. Let’s do some more of that since you’ve read this far. Check out where I’m at and what I’m doing now below:

Leave Your Troubles at The Door promo video
opening Leave Your Troubles at The Door, Funhouse Lounge (2022) — photo credit: Emily Ulsh

If you’d like to support me in my next big thing (and you live in the Portland, Oregon or surrounding areas), please come out to a ONE YEAR ANNIVERSARY Leave Your Troubles show the first weekend of March. We’re doing a special double header with a 3/3 10 PM show at Funhouse Lounge and a 3/4 4 PM Helium Comedy Club PDX debut show. I’ve linked the tickets above. I’m hosting both. I also couldn’t be more excited for the future. Here’s my website if you’re interested in finding my upcoming dates, more stand-up clips, etc. Thank y’all again for reading!

Here’s to another 10 years. [clinks glass]