The fact that comedian Jon Gabrus is thriving should not come as a surprise to anyone. The host and creator of the wildly popular Headgum podcast, High and Mighty, moved the show to his home studio during quarantine, and it’s where he’s been recording for over the past year. In fact, his first podcast has been so successful, it spawned a second: The Action Boyz, which he hosts along with Ben Rodgers and Ryan Stanger, “breaking down, discussing and ruining all of your favorite action movies.”
When we connect by phone, Jon is enjoying a weed-and-chocolate cold brew, purposely consuming cannabis earlier in the day so that his high will coincide with his High Times interview. Our conversation touches on Jon’s foray into comedy, his relationship with weed and how he quit toking in high school to focus on becoming an FBI agent.
Comedian Tells All
You started pursuing comedy after hosting your high school talent show. Was comedy something you were always drawn to?
I’m sure I have a traditional X-Men origin story in that I was always the class clown and always enjoyed making my classmates and teachers laugh. Anyone who seemed like a hard laugh was my favorite person to try to crack.
I really wanted to go to school to be an FBI agent, and my plan was to major in science, get into the FBI and become a special agent. I’d actually smoked weed in ninth and tenth grade and then quit because I’d heard somewhere that the FBI wants to make sure you’ve never done drugs before.
When the opportunity to host the talent show arose, the teacher producing the show was like, “Nah, you want to be an actor or a comedian or something. You should host the talent show.” I was like, “Oh, I don’t know.” This was my AP Psych teacher whose class I was taking because, again, I wanted to be a profiler or some shit—and she was like, “No, you want to work in entertainment. Trust me.” I was already set to perform a segment at the show with some friends, lip-syncing to Michael Jackson songs in stupid costumes, so I was like, “Okay, whatever.”
Performing on and hosting the talent show made me feel so fucking alive. My portion of the lip-sync was “Smooth Criminal.” It was 1998 or 1999, so I now understand the problematic issue around Michael Jackson, but, at the time, we had no idea. Screaming, “Annie, are you okay?” while the entire crowd sang along was such a fucking experience. It was like, “Oh, I get it now. I didn’t understand it before, but now I get why theater kids go crazy.”
So, that was sort of the catalyst for me, and while I thought I’d still pursue biology and join the FBI, I knew I now liked comedy. I didn’t realize all those times I was making my teacher laugh or making my brother laugh when I wasn’t supposed to, how much juice I was getting off that. With the talent show, it solidified how much I enjoyed performing.
Flash forward, day two of college, there’s an activities fair, and I was being a wise-ass, goofing off with everybody, and someone from the theater company asked me to sign up for the comedy group. That was it for me. I switched my major to Communication and focused on figuring out a way to work in comedy. I didn’t even know what it meant at the time to work in comedy, I just knew that’s what I wanted to do.
What was the experience that occurred along that path which made you realize a career in comedy would actually be possible?
If I’m being honest, it’s probably like a death of a thousand cuts or whatever the opposite of that is: A life of a thousand loads. It was born out of a lot of small events.
After college, I was a PA at VH1 for a little while, working on the show Best Week Ever. I would also transcribe comedy tapes and take comedy classes at UCB. I was surrounded by a lot of comedy, but was trying to get more into writing, producing and being in comedy. My friend Kevin [from VH1] was like, “Everyone here is going to think of you as a PA forever, because that’s how they met you. You’ll have to leave to become a comedian.” Whereas, I thought, “Maybe they’ll just let me be on camera on Best Week Ever.”
Kevin was like, “No, that’s not how it works, you 24-year-old idiot.” Which was completely fair. At the time I was like, “Paul Scheer, Doug Benson—these guys are pretty funny. I’m also pretty funny,” not realizing they had put in the 10 years of working in comedy. Kevin sat me down and told me I could leave, collect unemployment, find myself and start performing on shows and helped send me on my way. That was the last time I ever had a real “full-time” job in 2006 or 2007.
I went off, started coaching and teaching improv and took weird freelance jobs at everything from temping, to dressing up as a main character from Balls of Fury, to taking photos of people at bars. I took on the kind of weird jobs you see in these tv shows where they’re handing out fliers on the street—I just did the dumbest shit. I took psychological tests at Long Island College, anything I could do to make money living in Brooklyn. At the time, I was performing comedy, watching comedy, writing comedy, studying comedy – that was my real grad school, the couple of years I lived in Brooklyn, broke as fuck, eating rice and beans four nights per week.
When I’d go out with friends, I’d put all the drinks on my credit card and then collect cash from everyone so that I could have cash for the week. I’d then put that credit card bill onto a different Discover card and pay the transfer fee until I eventually moved in with my wife. Both of us had racked up like $30,000 in credit card debt trying to live in the city on full-shift, entry level jobs. I look back at that period of my life and see how from 22 to 27 is when I was learning how to be an adult while simultaneously learning how to be a comedian.
I’m even hesitant to use the word “comedian.” I’ve been performing comedy for 15 years, and I am still afraid to say I’m a comedian because it feels it’s a title owed, earned and applies to stand-up comics, not so much what I do. Even though I have performed stand-up, I don’t consider myself a stand-up comic because I’m such a fan of art, and I’m embarrassed to say that what I do is the same thing that Chris Rock does.
That’s why I always say that I “do comedy” and not that “I’m a comedian” because I feel like stand-up people own that. I “do” comedy in a bunch of ways, so maybe I am technically a comedian? I don’t know. These are all my issues that I’m unpacking.
So your “win” was really you going through the grind and betting on yourself.
There’s been so many other victories along the way, and a lot of them are weirdly tied to financial freedom. For example, me no longer needing to be an improv teacher felt like a victory because I was just performing without worrying about other survivor jobs. Podcasts are my “day job” now, as of a few years ago, and every step of the way has felt like a tiny victory.
What was the inspiration behind your podcast, and what do you think has helped propel its growth?
I was having a lot of fun guesting on my friends’ podcasts when people started Tweeting at me that I should have my own podcast. I started to think, while I’m doing all of this work on other people’s podcasts—and having a blast—I’m not making any money. I didn’t know what show I’d even want to do.
Luckily, my friends Jake and Amir—who I’d known in New York from doing bits for College Humor—said they were launching a podcast network and thought of me as one of their funny friends who didn’t have a podcast at the time. I told them I’d love to, but there was a catch: I didn’t want to do anything beholden to a premise and would want it to be as self-serving as possible without knowing at the time that pretty much every podcast is self-serving.
I ended up launching my first podcast, High and Mighty, as a less agro, less masculine Joe Rogan show—five years ago, and it’s now over 250 episodes and is as self-serving as possible. I haven’t stuck with anything for five years except podcasting and smoking weed.
Speaking of weed, how is it part of your life now as an adult?
As I said earlier, I quit smoking in high school. In college, I was a big-time party animal, but my roommates were potheads and were sort of annoying when they smoked weed, so I never really wanted to get high with them. Somehow, I also made it through college without getting into weed.
When I was 25 or 26, I smoked at my buddy’s bachelor party for the first time in a long time. I was a pretty heavy drinker then and was like, “Man, this is so much better than drinking.” At the time, I was only looking [at smoking] as an excuse to get a little lit, but over the past 13 years, weed has become part of my life. I named my podcast “High and Mighty” because it’s a quadruple entendre of how I’m a big boy; I’m a strong boy; I’m frequently stoned, and I’m high and mighty about my beliefs.
Cannabis is part of my creative process, and it’s part of my bonding experience. I often get lit with my guests on the podcast—though it’s entirely up to them if they want to get stoned or not—but for me, weed is something I use as a carrot. I don’t need it to get through the day, but it does help me get through the day. I’ll use it as a carrot in that I’ll get some work done, get in some exercise and not blaze until three o’clock. Part of me is like, “Just wait,” so I can have something to look forward to each day.
So cannabis for you is a means to relax, but also a prize for doing what you set out to do.
I also use it for pain and stress management. Weed is anti-anxietal for me, and one of the ways my anxiety manifests itself is in GI distress. The way my GI anxiety manifests itself it’s in poop anxiety, in that I have to poop before I leave the house because I’m afraid I’ll have to poop elsewhere. I’m afraid to go to the gym and have to poop there. Smoking or ingesting cannabis settles my stomach, and it’s such a freeing thing.
Also, the things I enjoy in life are video games, movies, conversations, eating, cooking—all the shit for which cannabis is a performance enhancer. I know it’s hack and that a lot of stoners don’t want to get caught saying this, but when they say that most cool stuff to do in life is better when you’re high, there’s a reason.
People aren’t just making it up.
That’s the only thing that bothers me. Whenever a non-stoner is like, “Oh, let me guess. You think we should get high because you think it will make the movie or the restaurant better?” I’m like, “Why are you judging me? Most people believe it makes food taste better. Why are you looking at that as a negative?”
Regardless if you’re getting high or not, if you’re both enjoying the experience in your own ways, that’s what matters.
That’s exactly my point of view. I’m also in my late 30s now. I can’t really be hungover anymore; I don’t have kids, and I don’t have that much responsibility. But I do like the ability to get up and exercise every day. Turns out, some of my previous GI distress was probably from alcohol and gluten, so getting rid of that has made me way healthier. Now, I just get stoned and drink soda water, and I feel so much better about myself.
When I’m creating, I like to write some of the day sober, and then get high and revisit and jam out “weirder,” more free-flowing ideas. Part of the reason why I think I have a good relationship with pot is because I didn’t smoke it in college when I had no responsibility and could have easily been the guy who was having trouble at school because it’s way more fun to smoke weed than it is to go to class.
Now, with no class to blow off, it makes it a little easier to get baked on a random Monday morning. Like today, we’re talking on a Monday morning, and I had to start the day with a little weed chocolate cold brew. As I said, I normally start at three, but some days, you just have to start earlier.
Author: Stephen Laddin