Brady O'Callahan TALKS ACTING, writing, comedy, and being true to his roots 

By Dyon Pumes

Photographs by Ian Stroud

November 22, 2017

Brady O'Callahan is an actor, writer, and improviser based out of New York City. He can be seen performing at the Upright Citizens Brigade Theatre on Tuesday nights with the Harold team Mermaids, as well as a grab bag of other comedy shows around NYC. Brady is a features contributor for The Onion and stars in the web series "Business Work” as well as “Roommates Making a Web Series About Roommates Living in New York City: The Web Series”, which have been featured on Funny or Die, A.V. Club, DailyDot, & Splitsider.

Brady works in fashion and regularly gives his fellow comedians advice on what they can wear to weddings. He also writes about culture/music for The Indypendent as well as his occasional concert newsletter “A Show Sometime”. He’ll talk to you about clothes or music forever, either one.

Jacket, $900, by Gant Rugger / Sweater, $80, by Club Monaco / Pants, $70, by Levi / Boots, $365, by Wolverine / Sunglasses, $150, by Ray Ban

Jacket, $900, by Gant Rugger / Sweater, $80, by Club Monaco / Pants, $70, by Levi / Boots, $365, by Wolverine / Sunglasses, $150, by Ray Ban

Brady's had a landmark year of coming into his own. Between his work on stage, his writing online, and anything else that pops up in between, he's had no trouble staying busy. You sort of have to, though, in New York City, if you want to have any chance of staying afloat. For Brady, it's sink or swim, though he still finds opportunities to ride the tide every once in a while.

As autumn draws to an end and winter quickly approaches, we thought we’d take Brady and photographer Ian Stroud to some of our favorite Brooklyn spots: The Rooftop, Prospect Park, and The Good Ol’ Shuttle Train Between. Then we sat down with O’Callahan at his favorite neighborhood coffee shop for a cup of jo and a raw conversation about Midwest identity, country music, and the challenge of standing apart in a sea of talent.


Brady O’Callahan is done with caffeine, at least for the time being. “I just found myself struggling to get up in the morning,” he tells me. “I used to go through three, four cups of strong coffee a day, and I just felt myself needing it to survive.” No more of that, he implies as he sets down a pair of mugs filled to the brim with what I had before assumed was coffee.

“Decaf,” he assures me. “You’ll be surprised, I swear.”

Jacket, $1500, by Gant by Michael Bastian / Shirt, his own, vintage The Hustler Collection / Pants, $70, by Levi / Boots, $365, by Wolverine / Sunglasses, $295, by Saturdays NYC

Jacket, $1500, by Gant by Michael Bastian / Shirt, his own, vintage The Hustler Collection / Pants, $70, by Levi / Boots, $365, by Wolverine / Sunglasses, $295, by Saturdays NYC

Down the hatch it goes, and while I don’t necessarily feel the same rush I get from a standard cup of mud, I’ve got to respect his control. Brady’s recently been trying to focus more on bettering himself, in every kind of way, really. Caffeine’s just the kick off. The almond croissants in front of us, a minor deviation. “Can’t get hung up on everything. I’ve learned to let myself enjoy the here and now a bit more, which, without getting too hippy dippy, necessitates taking care of your soul just as much as your body, you know?”

He punctuates many of his statements with this phrase. Some might see it as just a verbal habit, but even from spending a moment with the comedian, you get the sense that he really wants to communicate, connect. He wants us to understand each other, and in those moments where I didn’t “know”, he was eager to reach back and pull me onto the same page, where we were of the same mind. He tells me that his work on the Upright Citizens Brigade Theatre stage in New York tries its best to do just that: “I just want to make people laugh at things they see in themselves.”


He's been performing at the New York comedy institution for six years now, and he has no plans of slowing down. "I've poured a lot of myself into my work there, and I want to pour more and more. I want to try new things, take bigger risks." When asked what comes after, he cracks a smile. "I have no idea. Isn't that terrifying?"

The fear doesn't scare him, if that makes any sense (it only partially does to me). "I'll do stuff outside of UCB, but it's always nice to know I've got a home to come back to. I've met the most intelligent, funny, talented people at that theatre. It's intoxicating to be around." Intoxicating is an interesting way to put it. You get the sense that Brady gets wrapped up in moments. He seems significantly present in a way to most people struggle to be. For him, conversation and social interaction, even just joking around, is a drug. "I go a little crazy if I haven't had the chance to goof around with friends or on stage. Doing comedy keeps me sane."

Brady relaxes a bit back into his chair. He appears comfortable in his blue jeans, grey henley, and Wrangler western shirt. His down home look sings of his Midwest roots, but his long blond hair (this is new for him) and beat up slip on Vans (these are very much not new for him) hint at a California longing. When I ask him what he likes about this particular coffee shop, he replies, quite simply, “It’s close, it’s cozy, and they’re kind.”

Jacket, $1095, shirt, $225, pants, $395, tie, $145, by Michael Andrews Bespoke

Jacket, $1095, shirt, $225, pants, $395, tie, $145, by Michael Andrews Bespoke

Dyon Pumes: Let’s start with home. You’re from Ohio, Cleveland specifically. How do you think the experience of growing up there shaped your comedy?

Brady O’Callahan: I think growing up there gave me a lot, but I also think it kept me from a lot too. I think it taught me a lot about losing, and how that's good to do, because at least you're trying and learning from it. I mean, I was raised a Cleveland sports fan, which, up until recent years, was an oft told story of tragedy and heartbreak. I don't want to be one of those comedians or artists that say that heartbreak and sadness and all that stuff is necessary for comedy. I think that's a really dangerous and harmful attitude. There's nothing fucking wrong with taking care of yourself and trying to be happy, but I do think experiencing your fair share of blows grounds you a little bit.

You've got to lose sometimes.

Yeah, exactly. I mean, I fully admit that what I'm talking about is crazy. I also don't like sports fans who get so wrapped up in the whole thing that their happiness lives or dies by what's on the scoreboard, but growing up in Cleveland at the time that I did, that was at least a little true about everyone.

This is the 90's?

Yeah, 95 and 97, when Cleveland was in the World Series. I loved those teams. Regardless of the outcomes, I think it's great to care about things, to a healthy extent. I think growing up in Cleveland taught me that, and that's definitely influenced my comedy. I like playing people who care. Whether or not it's too a healthy extent is up in the air. [laughs]

Honestly it's probably just me projecting. It's probably moreso that my aunt lived in Cleveland and would put on the SNL "Best of Chris Farley" tape every time we'd visit. I fell in love with him and comedy.

The other side of it is that I grew up mostly around people exactly like me, so I was only ever really exposed to one slice of culture and comedy. That's why I love New York so much. There's so many people here with such different backgrounds and voices that it's easy to get inspired. I'm a much better comedian, and person I think, just because I didn't stay in one place telling jokes into what may as well be a mirror. I don't know. I feel like I'm learning a lot about comedy from a lot of different people right now, and it's just really refreshing to experience comedy from new perspectives.

So is your comedy changing now?

I hope so! I'd like to think I'm always learning and refining and trying new things. I'm still always going to have my tastes and my experiences, though.

You like playing the loser who cares.

[laughs] Yeah that sounds right. I think there’s a sort of humility that goes with it, not necessarily in that I’m humble about anything, but I love being the butt of the joke? I spent my whole life not trying to get in trouble, trying not to offend anyone, trying not to inconvenience anyone. I think taking that sort of personality trait where we minimize ourselves out of subjection and playing with it is super funny. I love low status. There’s nothing funnier to me than an earnest idiot, someone who wants so desperately to understand but just never will.

"There's nothing fucking wrong with taking care of yourself and trying to be happy..."

Jacket, his own, vintage Wrangler / Shirt, $165, by Gitman Vintage / Pants, $70, by Levi / Boots, $365, by Wolverine / Hat, his own, vintage Country Gentleman

Jacket, his own, vintage Wrangler / Shirt, $165, by Gitman Vintage / Pants, $70, by Levi / Boots, $365, by Wolverine / Hat, his own, vintage Country Gentleman

Nothing funnier?

Few things! Honestly, the funniest thing in the world to me is saying “ok.” It’s the same sort of thing, really. That response is pure acceptance, and yet it’s not completely blind. The person completely recognizes the situation and appreciates the fact that nothing can be done to change it for the better or worse. All they can say is “ok.” It makes me laugh so much. My friends have started commenting on all of my social media posts with “ok” because they know this about me, and, I’ll be honest, it hasn’t gotten old.


[laughs] You get it.

It's really funny to me that the smallest thing in the world tickles you that much.

Yeah, me too. I just think that real life is funny. Sometimes people try really hard to invent new unusual, crazy things for characters. A lot of the time I think we're weird enough.

That can be tough for some people to come to grips with.

They've got to get over it. Being weird is great. Weird is interesting, at least. People try to hide that sort of stuff in a lot of ways, especially online. Social media can be so performative, you know? In good ways and in bad.

Does social media ever interfere with your life? I hear a lot from people in creative fields that it can be a bit of a black hole.

Oh definitely, it’s the worst. But it’s also the best. I love that I can connect with like-minded people across the country. I actually keep somewhat in touch with friends that, if I had been born ten years earlier, I probably would have lost touch with long ago. But, yeah, you can waste a lot of time on Facebook and not even realize it. You can post jokes to Twitter and get quick reactions to it, and it feels like you’re accomplishing something, but sometimes I wonder if I really am? Some people treat Facebook and Twitter like an art, a comedic platform in itself, and I think it’s super fucking cool, but I don’t know how you turn that into anything, especially when you’re trying to break into the industry.

Everyone’s looking for their entry point.

That’s the thing, it’s got to be their entry point. It’s an entry point for you and you alone. No one method is ever going to be the way to do it as soon as it’s been done. Abbi [Jacobson] and Ilana [Glazer] made a web series that ruled, and they put it in front of the right people. Boom, they’re comedy royalty these days. That one dude wrote that 9/11 Seinfeld spec and gets hired by Family Guy. I think those ideas are done, and you can try your best to replicate their method, but it’ll only ever be your version of their method, you know? And who knows where that will lead?

So what’s your method?

Honestly have no idea. I’m figuring everything out right now. I’ve considered trying to leverage my love for music into something for a while, but I’m not sure what that looks like yet. I’ve been writing about music a lot recently, not comedically, but from a journalistic approach. Reviews and profiles and stuff like that. It’s been really refreshing to have a creative outlet without a sense of a finish line looming over you, you know?

Then again sometimes I worry that I have too many interests, that I’m spreading myself too thin, and I should really just drop all of this extra shit and focus only on writing thirty minute sitcom scripts or workshopping a character reel.

Even the thing that you do to relax can cause you to worry.

Yeah man, but that’s the thing: everyone worries about everything all the time. I’m a pretty zen guy for the most part, and even I get lost in my head. Sometimes I just need to tell myself to shut up, throw on a country record, and kick back.

"Being weird is great. Weird is interesting, at least."

You’re a big country fan, and to be honest, I’ve never really understood it.

Me specifically being a fan? Or country music?

I guess both.

Well I grew up with it a little bit. None of the old school folks like Johnny Cash, Buck Owens, Loretta Lynn. My parents listened to country radio in the 90s, so I was raised on John Berry, Vince Gill, Mary Chapin Carpenter, who I guess would be considered old school these days. I loved it, because I loved music, and that was the music that was most often played in the house or car on the way to school.

I fell out of love with it as I grew older, but a few years out of college I found bluegrass music, and it just rekindled the fire. I found stuff like Sturgill Simpson and Chris Stapleton and Chris’s old band Steeldrivers. They brought an energy and grit to country music I’d never heard, so I just dove deeper and deeper into it. It’s a music that feels very familiar to me, but there’s so much good country music coming out these days. It’s really incredible. Have you heard of Nikki Lane?

Can’t say that I have.

She’s incredible. Just this badass woman making phenomenal, exciting music. I read somewhere that she’s been called the First Lady of Outlaw Country.

Like Townes Van Zandt?

Townes, Merle, Waylon. All those guys! There’s a bunch of incredible women making country music right now, and most people have no idea. Margo Price, Whitney Rose, Lilly Hiatt, Jaime Wyatt, Kacey Musgraves, Miranda Lambert. I mean, people know Miranda, but I don’t think people know that she’s putting out the best records of her career right now.

Nikki's probably my favorite right now, though. I just saw her recently when she came through town. Her voice is unstoppable, and her band, The Tennessee Dirtbags, are unreal.

That's a hell of a name.

Right? I love it so much. I think country music can be smart and powerful, but it's almost never pretentious. I can't even imagine what a pretentious country record would sound like.

Me neither, I guess.

If anyone out there knows, please let me know. But, yeah, I feel like I'm doing street team work here for all my favorite artists. [laughs] I just get riled up by good music.

I’ll have to check it out. The other guy you’re big on right now is Colter Wall, right? You wore one of his hats for the shoot.

[laughs] Yeah. I’ve never been a big trucker hat kind of guy, but I saw it at the merch table when I saw him recently and picked it up. He was out of records. I should’ve bought one when I saw him in Columbus a few months back, but didn’t want to have to travel with extra baggage, you know? Anyways, yeah, I got it. I love it. I wear it! I just love his music so much. He’s a hell of a performer too. Definitely recommend checking him out if you ever get the chance.

Jacket, his own, vintage Wrangler / Shirt, $165, by Gitman Vintage / Hat, $25, by Colter Wall

Jacket, his own, vintage Wrangler / Shirt, $165, by Gitman Vintage / Hat, $25, by Colter Wall

I'll keep my eyes open, though i think the last concert i ever went to was in 2004.

Oh really? Who was it?

I have no idea, honestly. A friend of a friend.

Gotcha. I love live music. Try to get out and see it as much as possible. I have no musical talent whatsoever, at least that I've explored, so I find that gluttony is my way of filling that hole in my life. I don't have a ton of friends that were ever in bands, at least while we've been friends. Been to a small handful of friend's concerts, though, and I love seeing people in that element. I perform at one of the coolest comedy theaters in the world, and I still feel like the lowest tier opening band at any given show is so much cooler than I'll ever be.

that's wild. Do you ever feel cool?

Yeah sure sometimes. I don't place a whole lot of stock in it, though. Look, if you leave this interview and decide to frame this piece as an exploration of a cool person, I'm certainly not going to be upset at that. I just don't need it, you know?  I feel like once you make it to 25, no one gives a shit how cool you are. People just care that you're nice. Anyone who isn't an asshole is cool in my book. Anyone who finds something they care about and works hard at it, that's as cool as you can get. Passion is cool. I don't know, it all goes back to that same sort of thing I was saying before. I just like it when people care. About something. About others.

Jacket, $1095, by Michael Andrews Bespoke / Shirt, $27, by Wrangler / Pants, $70, by Levi / Boots, $365, by Wolverine / Pocket Square, his own, vintage Polo Ralph Lauren

Jacket, $1095, by Michael Andrews Bespoke / Shirt, $27, by Wrangler / Pants, $70, by Levi / Boots, $365, by Wolverine / Pocket Square, his own, vintage Polo Ralph Lauren

About yourself.


You've been fairly vocal about making more concerted efforts to do that sort of stuff.

Yeah, I guess I sort of have. I think there's something powerful about accountability, and I think vocalizing your desire to take care of yourself to others will make you more likely to follow through. There's a little bit of the fear of letting someone down in there too. I don't know if that's a healthy source of motivation, honestly, but I do think it works. That's why classes work. And writing groups. You don't want to let anyone down.

So what have you been doing to hold yourself accountable? What are you working on getting better at?

I've been hitting the gym pretty regularly. It's amazing to me how much better I feel mentally just from doing something physical. It's one of those things that everyone always says, and for some reason you never expect to be true. It is, though. On days when I miss the gym, I feel a marked difference in my mood and overall productivity. I'm not, like, model fit or anything, but I feel good! And I like that enough to keep it up.

Other than that, I guess I'm trying to get back into meditation. I'm going to sound like one of those people right now, but my limited experience with meditation has been great. It just helps me process everything in a healthier way when I sit down for 10 minutes each morning.

You said get back into it. You're not doing it regularly right now?

Woof, no. I fell out of the habit. Honestly it's been months. I really need to get back into it though. I paid for the damn app! [laughs] I guess I'm doing that thing again where I'm vocalizing it to you in hopes that I'll force myself to sit down and do it. If you could pretend to care that I do, that would help me a lot.

I'll follow up tomorrow.

[laughs] Good!

"I think there's something powerful about accountability, and I think vocalizing your desire to take care of yourself to others will make you more likely to follow through."

Can you describe where you've been living? what's your space like?

Sure, yeah, I've been living in Crown Heights for the past two years. Got a handful of roommates, love them all. We all keep to ourselves for the most part, but every once in a while we all find ourselves in the common living room area just chatting and catching up. It's a really nice balance.

I used to live in another apartment and thought that New York City apartments were super temporary, so I never invested in my space. I never even put art up on my walls. It was stark and bleak and essentially a place to sleep. I lived there for 6 years.

That's a long time for a New York City apartment.

Tell me about it! By the end, I just couldn't wait to start over somewhere else. And that's what I did. I tried to make my room a place where I'd want to spend my time, because the fact is that I spend most of my time there. I write there. I got a new record player and set up all of my records there. I love my room now. Oh my God I got a few plants! Those things will do wonders for a space.

First time plant owner?


They're nice as long as they don't die.

Oh I got the ones that you'd have to actively try to kill. They've come close for sure. I'm still learning.


So you've been in new york for a while now. feel like the question most comedians get asked is if they're planning on moving to los angeles any time.

Yeah, for sure, I've been asked a million times.


Eventually, probably. I've been out there a bunch. I like it a lot. I've got a lot of friends out there, and I'm sure I'll have more and more friends out there as time goes on. I think the answer is probably yes, but definitely not yet. I've still got a few things I want to check off on my New York list first.

The weather isn't half bad out there.

Oh hell I know. I grew up on the east side of Cleveland, where we had terrible lake effect snow storms. It snows in October there and stays til May. I can't help but feel like I'm a little over winter. I wouldn't mind waking up and not having to check the weather every morning. People say it gets boring, which I barely understand. I'm of the mind that I can travel to experience other weathers the way most people travel to experience weather like LA. Why wouldn't I want my default to be sunny and beautiful? That's crazy to me.

Who knows, though? The way climate change is going, New York could be the new LA in 10 years. For all my hang ups with winter, I still love having snow around Christmas. It can piss off after December, but it's necessary for me that month.

Last year on Christmas it was 60 degrees in Cleveland. I was so bummed. That doesn't feel like Christmas to me.

Well Christmas in LA is going to be sunny and beautiful. Will that feel like Christmas?

Ehh. I'll go to Disneyland, and that'll pick up the slack.

You're a Disney fan?

I adore Disney. Those parks are unbelievable.

Sweatshirt, $115, hat, $50, by Saturdays NYC / Pants, $70, by Levi / Shoes, $90, by Adidas

Sweatshirt, $115, hat, $50, by Saturdays NYC / Pants, $70, by Levi / Shoes, $90, by Adidas

What's the one in Florida? Is that Land or World?

That's Disney World.

I've never been to that one.

I don't want to be that person that says you have to, but you have to. It's incredible. It's interactive theatre, the whole thing. It's a show, and it's damn fun. There's something about being in a place where you know thousands of people are having the best day of their life, guaranteed. It's magical.

It is pretty wild that they've built this enormous empire that seems to have a monopoly on happiness.

I’m reading this Disney biography by Neal Gabler right now, and it’s super incredible. He was a really interesting dude. Super motivated and absolutely reckless for most of his early career. He was so close to losing it all so many times. I had no idea. I’m a pretty big Disney fan, and I love the lore of early Hollywood, so this is a real good read.

Jacket, $398, by Club Monaco / Shirt, $109, by Portuguese Flannel / Tee, $28, by Buck Mason / Pants, $70, by Levi / Shoes, $90, by Adidas

Jacket, $398, by Club Monaco / Shirt, $109, by Portuguese Flannel / Tee, $28, by Buck Mason / Pants, $70, by Levi / Shoes, $90, by Adidas

Have you listened to "You must remember this?"

The podcast? Yeah, I've listened to a few. It's great. I love hearing those old stories from that era of the entertainment industry. Admittedly, I'm not a huge podcast person in general. I have my favorites, a few, that I listen to, but I only ever listen to them at the gym. I can't do anything that's too educational, if that makes sense. If I can't glaze over and jump back in, it's probably not going to work for me.

I love "Uhh Yeah Dude." It's just these two guys riffing on recent news stories and things like that. It sounds like a terrible idea for a podcast, or at least super unoriginal, but these guys are incredible. They've also been doing it forever, so as far as I know, they called dibs on the whole idea of a riff podcast. They're so fun and funny and charming. They've got this rapport that's so rare anywhere. It's undeniably engaging.

But yeah, I'm not really a podcast a day kind of guy. I try and read on the train, and when I'm not doing that, I'm listening to music. I like to stay on top of those things.

That's another thing that I like about New York. I can just tune out on my commute. Can't really do that in LA. Maybe I'll move when I catch up on all these books and albums I haven't listened to yet. [laughs]

might take you a while.

Yeah that's fine. I'm not in a rush.

Any pressure to make career moves any time soon?

I try not to think about it like that. I feel like as long as I'm happy doing what I'm doing right now, that's good. If success comes down the line, I'd love that too. But I'll get there. I'm not spending my days goofing around, you know? I'm definitely trying to make stuff happen. I'm just not upset that stuff hasn't happened yet.

That's good.

Yeah, I think so. I think you have to feel that way, especially when you see stuff happening for people, peers, around you. You can't get hung up on other people's timelines. Focus on your own shit. Get good at what you like. I don't know. I guess follow up with me in 10 or 20 years and see if I still feel this way. I'm still young and dumb enough to keep plugging away at my own speed.

Suit, $1795, pocket square, $59, by Michael Andrews Bespoke / Tee, $42, by Buck Mason

Suit, $1795, pocket square, $59, by Michael Andrews Bespoke / Tee, $42, by Buck Mason

Any regrets?

What’s that?

Like big life regrets. Stuff that eats away at you day and night.

Wow, this interview’s really going for it now, huh?

Don’t dodge the question. What makes you uncomfortable?

Uhhhh...I think you need to cool it a little. This is getting intense.

"It's interactive theatre, the whole thing."


But I'm you.


Excuse me?

I’m you.

I don’t follow.

There's no one here, Brady. You're me. You're interviewing you. Can you stop yourself?


Uhhhhh I thought you were supposed to be Dyon Pumes [laughs].

That’s a made up name. It’s an anagram for “pseudonym.” You know this. You did this.

Wait, what?

I’m you.

What the fuck, dude?

You know this. You did this.

I, uh, I think I’m going to head home.

You’re already there.

We’re literally sitting in this coffee shop. I got you a croissant!

You’re sitting in your bedroom right now writing this. There never was a croissant.


Oh my God.

What the fuck is happening? WHERE DID YOU GO?



It’s ok, Brady.

No! No it’s not fucking ok! What the fuck is going on? Where are you?

You can’t get rid of me.

Fuck this I’m out of here!

You ok man?

No, I mean, I don’t know. There’s someone in my apartment.

Holy shit, really?

I’m not in your apartment.


Excuse me?

No not you. Sorry.

Oh, I get it. Nevermind, man. I hope you get help.



Let's go

2017-11-16 22.23.29.jpg



You can’t outrun this.

What the fuck what the fuck what the fuck

I told you, Brady, you can’t outrun this.


Oh my God.


What did you think was happening?Did you think you were really running? You’ve been sitting at your computer this whole time.

How do I stop this?

You can stop whenever you want.


I want it to stop.

So stop.


I don’t understand

I’m just you, a different side of you maybe, but you all the same.

Look, can we please just help me out. Can we talk this out? Can you show yourself?

Are you sure?

Yes. Christ, please.

Come find me.



I…I don’t understand.


Look for me in you.


What are you?

Like I said, I’m you.

No, you’re fucking not. I’m me. You’re some twisted fucked up version of me.

I’m you.


I’m you.

Stop it.

You stop it.


You stOP It. I caN'T STop it I dON'T KNOw how to STOP IT I nEEd you to stoP IT PLEAse pleasE I'M BEgging you. I caN'T TAKe this anYMOre this is DRIVINg me inSANE. I JUst wanted tO Do a fun LITTLE BIO THINg and this hAS GOTTEN TOo fucking insane. It’s too much. NO ONE IS GOING TO hire me with ANY OF THis bullshit! AND I DON'T EVen care aNYMORE.




I just want to go home.



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