Matt Ruby: “What I’ve Learned From 10 Years of Doing Stand-Up Comedy”

Longtime reader, first-time contributor.

Matt Ruby was one of the first people in New York City to come up to me and email me to acknowledge his support of The Comic’s Comic when I launched the site independently more than nine years ago. Ruby said nice things to me inside Rififi, and got me to notice his own comedy blog, Sandpaper Suit. Ruby since has gone on to perform not just across the city, but everywhere else, too. He co-produces and co-hosts a great back-of-the-bar showcase in Manhattan on Tuesday nights called Hot Soup. He makes and stars in a weekly webseries spoofing technology startups, Vooza, that has even garnered him speaking gigs and more around the world. With Mark Normand, Ruby has co-hosted and produced a great comedy gathering for the past several Halloweens called Schtick or Treat — which not only has spread to other cities, but also a filmed special on Seeso.

But not until now is he recording his first stand-up comedy album. That’ll happen Dec. 7 in Chicago at Timothy O’Toole’s Pub, presented by Comedians You Should Know. You can grab discounted tickets to watch him record it, via Brown Paper Tickets.

So I’ll turn the floor over to Matt Ruby to reflect on his first decade in stand-up comedy.

Note: This essay originally appeared on Medium, and is republished with the author’s permission.

Just realized this:

December, 2006 = I do my first standup show

December, 2016 = I record my debut standup album

10 years. Ten fucking years. That’s what I’ve given to standup comedy. Or did it take it from me?


The questions people usually ask: “Why’d you get started in comedy?” Because I wanted to tell the truth. I was never the class clown type. I’m kinda serious. But I love telling the truth and I realized that being funny was the best way to do it.

Another thing people ask: “Were your parents funny? Is that why you got into standup?” Nah, my parents aren’t why I do standup. In fact, my Mom hardly ever laughed at all. So, uh, oh…wait a minute. I do remember how much my dad loved Groucho Mark and Steven Wright. You could hear his laugh throughout the house when they were on the TV.

And I’d watch Bill Cosby and Eddie Murphy specials over and over. But the seed was really planted when I saw Chris Rock’s “Bring The Pain.” Still the best special ever in my book. It was like watching a magician. I wanted to know how to do that trick. Later, I’d listen to Mitch’s albums and Chappelle’s “Killing ’Em Softly” over and over with a coworker. It started to seep into my brain.

I wanted a taste. That’s why I started. Why’d I stay with it? Because it feels good. OK, it’s goddamn addictive. When it’s bad, it’s humbling. Everyone in the room knows you’re failing. It’s a raw, primal thing. But when it’s good, oh man, it’s really good. It’s like conducting a roomful of people in a symphony of joy. A maestro of laughter.

Either way, good or bad, it makes you feel alive. For someone who’s a bit, ahem, disconnected emotionally, that’s a powerful hit. Also, I crave validation. When it goes well, comedy gives me that. And it feels less selfish than other ways of seeking validation because you’re making people laugh. It feels like you’re giving back.

But oof, the beginning is rough. The open mic circuit. Microphones attract a lot of crazy. But also some really talented, hungry people. I think back to the people I started with. It reminds me of Band of Brothers. It’s a group of people who you share something with that you’ll remember forever. You’re bonded, like you’ve been in the trenches together.

Some of them have gone on to nice success in standup. Others chose different comedic paths, becoming writers or actors. Others quit. I envy all those groups in a way. Yes, even the ones who got out. I see their Facebook posts with their real lives and wives/kids and hobbies. They generally seem much happier. I wonder: What if I hadn’t caught this bug? Then I think about that Bill Burr quote: “Realize that sleeping on a futon when you’re 30 is not the worst thing. You know what’s worse? Sleeping in a king bed next to a wife you’re not really in love with but for some reason you married, and you got a couple kids, and you got a job you hate. You’ll be laying there fantasizing about sleeping on a futon. There’s no risk when you go after a dream. There’s a tremendous amount to risk to playing it safe.”

I get that. But sometimes it feels like a fever dream. Like I fell into a rabbit hole. Like I decided to poke my head into a doorway and I woke up ten years later, unconscious, in a bathtub, with one of my kidneys missing. There’s been a lot of pain that comedy has brought me. Onstage is almost always fun. It’s the rest of it that can sting. The constant gnawing that you should be doing more/better/harder/smarter. Then again, maybe it just highlighted a pain that was already there?

I’m single and I think about relationships that I lost, at least in part, because of doing comedy. But then I think about girls that I never would have met without doing comedy. I think about other life paths I could have taken. Jobs I gave up or turned down. Things I could have done instead. They recede in the rear view mirror as I race to do another spot.

It’s a life though. I do tons of shows for hipsters and tourists. And I do shows for dudes who work on an oil rig. I do jokes in London and Alabama. I travel alone a lot. I take a train to Canada to do jokes there. I get a ride from a stranger from Nashville to Chattanooga to do jokes there. I take a Greyhound bus from Portland to Seattle. I realize they call it Greyhound because that’s the only animal that’s been abused as much as the passengers. The guy who runs the show in Seattle hangs himself in the alley a year later. I follow a comic who explains why white people suck for ten minutes. I’m introduced by a host who talks all about a dead soldier friend who died in Afghanistan before bringing me up. I perform in a college cafeteria at noon in front of six kids playing Magic The Gathering and the school mascot. I do shows for black people in Harlem. I do shows for Jews in a synagogue. I do show for Christians in a church. I do shows for gamblers in a casino. I do shows where there are little kids in the front row. I’m constantly talking to people I would never talk to in “real life.” It drives me crazy and keeps me sane. I do shows. It’s what I do.


Standing in front of a roomful of people who are judging you every night changes you. Those people might be idiots as individuals, but together they have a wisdom. They see through you. They tell you every night if you’re being authentic or if you’re just reciting some lines. They shrug at things that excite you. They lose it at the things you think are nothing. They make you question yourself all the time. They’re right. Even when they’re wrong, they’re right. They are your partner in creation.

You can’t do standup alone. You can’t practice in a room. That’s what makes it so amazing and terrible. The analogy I give to civilians (that’s what we call you people who don’t tell jokes): Imagine trying to win the gold medal in swimming. But you can only get in a pool for 10 minutes every night. That’s what it’s like trying to do standup.

Plus, I’m doing it in New York City. It’s the best place to get good at standup. But that means I live in one of the most abusive cities in the world (I kinda think everyone who lives here is in an S&M relationship with New York City). Then add on pursuing one of the most abusive professions there is. It’s a recipe for getting beat up. There’s a reason many drop out or turn to substances. I’m trying to do the mindful path: therapy, meditation, etc. But you’ve really got to keep your hands on the wheel at all times.

You can’t help but get jealous. Why’s he getting that instead of me? But the answer is usually that he works harder. I don’t know if I’ve worked as hard as I could. I’ve had other jobs while doing standup. I’ve prioritized other things in my life while others are single-minded. I’m trying to be a whole person. In comedy, that’ll hold you back. But then I think about the foolishness of trying to do this sort of comparison. A question I prefer: Would I choose to trade lives with that person? Because I’m pretty happy with the life I’m living. I’m pretty lucky. I know it. (I just knocked on wood.)

And I know others look up to me and see me as doing well. Due to the video stuff I do (Vooza, etc.), I’ve been able to make a living making funny stuff and working with people I like. That’s fucking amazing.

It’s so easy to focus on those ahead of you instead of those behind you. Or to even think ahead/behind exists. The truth is we’re all somewhere in the middle. Getting by. Trying to get to that next rung. And sometimes things click for different people at different times. I’ve always been a late bloomer. Maybe I just need to be patient.

Photo by Mindy Tucker.


You get into comedy because of the laughs and then you realize it’s often quite miserable. Talk about a bait and switch. You get rejected. You lose contests. You don’t get auditions. Bookers won’t reply to emails. Festivals turn you down. You interact with shady folks. People shake your hand while looking the other way. You try to be part of a community but it feels like this community is just a bunch of hungry wolves gathered around a table waiting for a scrap of meat to fall to them. It’s not that they don’t care about you, they’re just fixated on their own survival.

They don’t know me. About my life. They don’t know I was in a band. That I made albums. They don’t know I lived a life before standup. That I’ve written books. Where I worked. They don’t know about girls I’ve dated. They don’t know what my parents were like. They don’t care. They just know whether or not I got Montreal. The only question they ever ask is “Who books that?”

The whole thing gets to you. It wears you down. You start thinking about all the things you’re doing wrong. All the ways you are wrong.

I started too late.
I’m an old, straight, white dude. No one wants that.
I’m too low energy.
I care too much about making a point.
I’m not likable enough.
I don’t work hard enough.
I don’t ask for things.
I’m bad at networking.
I’m bad at faking it (onstage and off).
I want to have a life outside of comedy.
I’ve tried to be a decent boyfriend.
I maintain friendships outside of comedy.
I don’t write enough.
I’m not mainstream.
I should have a podcast.
I’ve focused on other aspects of comedy (writing, acting, producing) instead of standup.
I do that joke about my mom being paralyzed which goes ok instead of that joke about 69ing that kills.
I think about this stuff too much.
I write too much on Facebook.

And then there’s the scariest of all: Maybe I’m just not good enough. No matter how hard I work, I won’t ever be good enough. And I’ll look back at this as some wasted period of my life.

But I don’t think that’s true. Comedy has changed me. How I look at the world. How I think. How I examine things. It makes me want to pick up rocks and turn them over. It makes me want to play devil’s advocate. It makes me want to look at the consensus and search for holes. It makes me want to find the part that people aren’t talking about. It makes me obsessed with finding things that are truthful and yet surprising. That’s where the juice is. It’s given me a different way of seeing the world. I love that and wouldn’t trade it for anything.


I’ve changed while doing comedy. Was it because of comedy or would it have happened anyway? I feel more Jewish. I’ve started to study my faith more. What is it about Jews and jokes? I still don’t know but I’m trying to get deeper into it without turning into some mindless believer. My thought: If I love Larry, Jerry, Garry, Groucho, and other Jews so much, maybe I need to look into how Judaism makes people think. Basically: If I like running the app so much, maybe I should start looking at the source code. Eh, you don’t care. People talking about religion always sound like kooks.

Speaking of, I started doing therapy after years of standup. It wasn’t just because of standup. But standup certainly helped drive me there. Around the same time, I started taking acting classes too. Meisner. And something interesting happened: My Meisner coach and my therapist were both giving me the exact same advice. I need to feel more. I need to show my feelings. I need to emote. I push things down. My dad never said anything. I thought that’s how a man behaves. But people want to see you access those feelings, not repress them. I’ve gotten better at it. I’m still not there though.

It’s been a tough period in other ways too. I lost both my parents and my brother-in-law. I’ve processed grief through standup. I talk about it onstage once in a while. It feels off. Crowds don’t want that vibe. But I want to be authentic. Because you’re supposed to be authentic, right? But if your true story just brings people down…well, y’know. Maybe I should save it for a one man show.

I was about to go onstage the night my sister called and told me her husband died in a motorcycle accident. “Brian’s been involved in a fatal accident,” she said in a shaky voice. I thought, “So he’s dead or someone else is dead? That’s a funny way to say that.” It was as if my comedian mind could not be silenced. I went home immediately. But the truth is part of me still wanted to go onstage that night. It was a crowd. I don’t know how to turn down a crowd. I want them more than anything. It scares me.

In the past years, I’ve been participating in ayahuasca (hallucinogenic tea from the Amazon) ceremonies on a regular basis. It has given me perspective and clarity. I see where I fit in to the planet. Where we all fit into the planet. We are all so goddamn lucky to experience this life. Even if it’s painful or twisted or doesn’t make sense, we are alive. The sun is shining on us. Afterwards, we’ll go back into the dirt. This is your blossom. You can look down or open wide. It’s up to you.


This year has been good for me and comedy. I’m so proud of our Hot Soup show and the guys I run it with. I think it’s a great show. It feels like a real crowd we get there every Tuesday. We have regulars. That pushes me to write new. Schtick or Treat has become a weird sort of institution and this year it was aired on Seeso and we did it in LA. I’ve toured around the country doing standup. Comics I respect have said nice things about my sets. I’ve signed with a label to release my album. I just taped both a half-hour and 10min sets that I’m proud of and will be submitting to TV bookers. My Vooza show — that I make with an amazing cast and crew — has passed 160 episodes and it’s really good and it’s opened doors for me to perform at tech conferences and other places in character as an idiot startup CEO. I think about what Johnny told Steve Martin once: “You’ll use it all.”

And in the past few months, I’ve been grinding harder than ever at standup. I booked a date to record my album in Chicago and that put the heat on. I want it to be the best it can be. So I’ve been on the road. I’ve been writing more. I’ve been taking that 12:45am spot where I perform in front of drunk tourists who don’t speak English. I did a Week at the Creek where shows would start out in front of 2 people and end in front of 20. You just push through the beginning knowing that eventually it’ll get better.

And you start to see the difference. The engine starts to purr. The rhythm gets tighter. Things start to pop. You come up with new tags. Old jokes work better because you’re better now. Setups get shorter. You get more confident. They trust you more. You climb the mountain one step at a time. There’s still further to go. But I’m trying to remember to turn around and look how far I’ve come too.

I feel like a real comedian. I didn’t always. But I do now. I still don’t know if I’m great at the five minute tap dance set and I get how that hurts me in the industry game. But put me onstage for 30mins or an hour and I’ll get ’em. I have interesting points of view. I’ve got stuff to say. And I’ve got jokes. And it’s good. It’s funny. It’s me. It’s true. Is it going to get me on TV or get me famous or get me whatever else? I don’t know, but I’m proud of where I’m at. I’m a good fucking comedian.

It took me 10 years to get one hour. 10 years = 1 hour. Now that’s funny. Welcome to comedy, it’ll destroy you and make you new at the same time.


1-grmnmscfb91pb7ynhhqiugIf you’re in Chicago on Dec. 7, 2016, you can see Matt Ruby record his stand-up comedy album at Timothy O’Toole’s Pub, presented by Comedians You Should Know.

Sean L. McCarthy

Editor and publisher since 2007, when he was named New York's Funniest Reporter. Former newspaper reporter at the New York Daily News, Boston Herald and smaller dailies and community papers across America. Loves comedy so much he founded this site.

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