This is the Rubesletter from Matt Ruby. I’m a comedian, writer, and the creator of Vooza. Every Tuesday, I send essays, jokes, and videos to your inbox. You’re on the free plan, for the full experience, sign up for a paid subscription.

Q&A about my comedy journey, creativity, standup advice, and more

Also: My Korean Dad, jean style, the black lady therapist trope, David Byrne, etc.

Matt Ruby

Nov 16

I did a Q&A with Teh Chin Liang about standup comedy and creativity (reprinted below). In it, I discuss my comedy journey (love any “journey” talk cuz it sounds like I’m on “The Bachelor”), early/international gigs, creativity, standup advice, and lots more.

Q. In your article “What I’ve Learned From 10 Years of Doing Standup Comedy”, you said the reason you began stand-up comedy was because you wanted to tell the truth and being funny was the best way to deliver it. Tell us about your love for comedy and your journey into stand-up comedy? (How did you improve your skills to get to where you are now)

My therapist once asked me if I do standup comedy because my mom was funny. I replied, “No, I don’t think so. My mom wasn’t really that funny. In fact, come to think of it, she didn’t really smile much at all. So I don’t think that’s why I do comedy. Actually, my mom was pretty depressed. Nothing I did would ever make her laugh. So that’s definitely not why I get up in front of a roomful of strangers every night and try to make them lau– Ohhhhhhhhhhhh, I SEE now.” So I’d say the journey started there. Once I tried standup, it felt like falling into a rabbit hole…

“Alice had not a moment to think about stopping herself before she found herself falling down a very deep well.”

Also, I really like telling the truth and I realized that funny people seem to get away with doing it more than anyone else. A lot of my comedy is me trying to figure out a funny way to say what I actually wanted to say anyway.

Q. What is your recollection of your first gig?

My first few gigs in front of real audiences went surprisingly well considering my inexperience. My guess is I had an enthusiasm and naiveté that went over well during those early days. I miss being clueless; it’s liberating to not know what you don’t know.

At that point, I was delusional enough to think I was some kinda natural. It was only after a few bad sets that I began to see the actual path ahead of me and how much work it would require to get good. Then came the hard part: years of hanging out at open mics in dive bar basements in order to tell a few minutes of bad jokes while surrounded by unstable people because no one loves a microphone more than the mentally ill.

Q. Creativity is the key to comedy's engine. Tell us how you use creativity to construct a joke? How will you create your own version of a joke using the 3 beginning lines below? (Can you write a short joke for each)

1. What would happen to a guy in his 40s and has not been in a relationship ….

2. I used to have a girlfriend with an obsessive-compulsive disorder ….

3. I have been studying the Bible a lot lately, but it is not because I have become a devout Christian ....

Well, I kinda reject the premise of this question because I would never reverse engineer my jokes in this way. I prefer when jokes arise organically rather than via assignment.

My favorite way to come up with bits is to have conversations with friends and wait for something to come up that feels like a fresh take, gets me animated, or feels juicy in some other way. I carry a notebook (and use the Notes app on my phone) to capture those ideas in the moment. “Hang on, I gotta write that down.”

Then later on, I’ll flesh it out as an idea and, if it feels like there’s something there, try it onstage. Most of the time, they’re not actually strong enough to work as jokes.

Every once in a while, a joke comes out fully formed; but that’s rare. Usually, you’ve got to chip away at it for weeks (or even months) before it’s solid. The audience teaches you via laughs which ones are worth hammering away at until they’re actually funny enough to stick in the set.

But since you asked…

What would happen to a guy in his 40s and has not been in a relationship: Sounds like he’s going to join Reddit and either storm the Capitol or leave angry replies to posts from female journalists on Twitter.
I used to have a girlfriend with an obsessive-compulsive disorder: What happened with her? She washed that man (me) right out of her hair. And then washed him out again. And again. And again. And then she locked me out of the apartment. And unlocked it. And then locked it again. Etc.
I have been studying the Bible a lot lately, but it is not because I have become a devout Christian: I’m starting a cult and I want to get some tips about the best way to do it.

Q. There are many comedy clubs all over New York City. What are some of your favorites and what advice would you give to the first-time visitors to the city who are interested in catching a live stand-up comedy show?

I perform most frequently at the Comedy Cellar (including every Tuesday night at Hot Soup) and NY Comedy Club (including every Wednesday night on Good Eggs). Those are the best places to see a quality show that delivers a real NYC standup vibe.

Some tips: Get tickets in advance since shows frequently sell out. And weeknights are your best bet for bigger names to drop-in on a show since they’re often on the road during weekends. And if you sit in the front row, be prepared to answer whether or not you’re dating the person accompanying you. That happens at about 80% of shows. (Note: If you’re with someone of the opposite sex and you say you’re just friends, the host will say one of you is trying to have sex with the other and everyone in the room will explode in laughter because for some reason unrequited love is the funniest thing to human beings.)

Q. You have performed throughout the US and outside of the US - England, France, Holland, Israel, Canada. How do you make adjustments to ensure your comedy approach is relevant to the audience from different backgrounds and cultures? Will you do a show in Asia one day?

First off, I’d love to do a show in Asia. Asia, ask me to perform there (travel expenses included, please)! As for adjustments, I try to throw out anything that relies on pop culture/American references for my (occasional) foreign gigs because they’re likely to fall flat. And then I try to do material on universal topics like dating, technology, aging, etc. It’s a good challenge because it forces you to examine your material and figure out what’s relevant to everyone. Also, I make fun of the country that’s next door. Everyone always hates the people next door.

Q. What is one thing that you wish you had learned earlier in your life?

I wish I had realized the interconnectedness of the universe and that ego death is essential for becoming an enlightened human being. That and you should buy one of those trays that makes big ice cubes. They’re super cheap and people are irrationally impressed by large ice cubes.

Q. Tell us about the stand-up show that you co-produce – Hot Soup at Comedy Cellar in Manhattan. How did the Hot Soup name come about and why is it a fun show not to be missed?

The other show producers and I were at a diner spitballing name ideas and one of us ordered soup and then someone said, “How about Hot Soup?” And we all agreed because there’s something about diners and comedy. It’s now the longest running independently produced comedy show in NYC. We always book hilarious lineups with some of our fave comics. Plus, we encourage comics to try new material and take chances so it’s a great show for comedy nerds who like to see the process and can handle a few clunkers.

Q. If you have your own stand-up master class, what are the tips would you give to a beginner?

Well, I wrote a blog during my first few years all about standup and lessons I learned so I recommend checking that out: SandpaperSuit.com. Some tips: Perform as much as you can, watch/listen to great comedians, align what you talk about onstage with what you talk about offstage, make friends with your peers, think like a craftsman, figure out a healthy relationship with alcohol (because you’ll be surrounded by it), don’t be afraid to take a harder/longer path instead of seeking shortcuts, and don’t be jealous of other people’s success because everyone’s on their own path.

Q, Tell us about your life outside of stand-up comedy? (I know you love traveling photography too. Tell us about your unforgettable travel stories if you have any)

My life outside of standup involves writing, art, video production, music, meditation, psychedelics, photography, travel, and just trying to be a seeker in general. The challenge is talking about any of that without sounding like a pretentious douche.

As for travel stories, here’s one: I once went on a trek outside of Chiang Mai, Thailand and we visited a hilltribe community in the middle of nowhere. They were dirt poor but seemed very happy and it was a fascinating look at how most people around the world probably live. They woke up at dawn when the roosters crowed. And before they went to bed at night, they gathered round a campfire and drank moonshine whiskey and passed a guitar around. I remember being surprised that, despite knowing no English, their song choices were western staples like “Wonderful Tonight” and “Country Roads.” What really blew me away was how every one of the locals sang beautifully. Like *gorgeous* voices. And that got me thinking about how, in the west, we think you have to learn how to sing. But perhaps the real problem is that we’ve forgotten how to sing. Maybe we’ve gotten so far away from our circadian rhythms, we’ve lost our ability to harmonize. Our voices are pitchy because our lives are pitchy. The other thing I learned: Moonshine whiskey really packs a punch.

Q. What is one big breakthrough you want to see in your career?

Big breakthrough? Well, I’d love to careen through a brick wall while carrying a large pitcher of a juice-like drink while screaming, "Oh yeah!"

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Quickies

🌀 Morning shows are a great place to learn about our country's slide into authoritarianism from men who used to play professional football.

🌀 NFTs are commemorative plates for tech bros.

🌀 As soon as you bring herbs home, take the rubber band off so they can breathe. Think of it as the plant version of coming home and taking off your bra.

🌀 Seduction is a lost art because persuasion is now a form of violence.

🌀 I keep seeing photos of Emily Ratajkowski looking hot while plugging her book about how it's not important that she's hot and if only there was a phrase to describe this feeling that lines are being, I dunno, fuzzed?

🌀 Why are Jews so anxious and neurotic? We weren't always this way. There used to be relaxed, chill Jews. And they were like, "I'm just gonna stick around and see how this all plays out." And that's why there are no more calm Jews.

🌀 The big lesson of Sex and the City is if you're a slut and you hang out with people who are even sluttier, then you'll be considered "the prude."

🌀 Top reverses: 4) mortgage 3) image search 2) osmosis 1) cowgirl.

🌀 My AirPod case looks just like my dental floss and that's how I wound up charging my teeth.

🌀 I don't understand how employers get qualified people to jump through all the hoops of job postings. Who has time to fill out 75 questions and then write an essay to maybe get past the first level!? It's like being a grownup who’s forced to take the SAT again.

rubymatt

A post shared by Matt Ruby (@rubymatt)

🌀 This whole "Would you like to leave a tip?" while handing over a screen and maintaining eye contact thing we're doing now feels less like a tip and more like a shakedown. Fine, I'm tipping you...but this is NOT enthusiastic consent.

🌀 "Now the largest living generation, [millennials] control just 4 percent of America’s real estate equity; in 1990, when baby boomers were a comparable age, they already controlled a third." (From Will Real Estate Ever Be Normal Again?) Boomers have run a helluva generational scam!

🌀 The hardest part of being a serial killer now is convincing your siblings to never do a 23andMe test…
Killer: "You can't give them your saliva...it's, um, an invasion of privacy."
Sister: "C'mon, you sound crazy."
Killer: "Oh sis, you only know the half of it."

🌀 My dad was a prosecutor and my sister was a cop and my mom smoked weed and I took shrooms so, y'know, it was THAT kinda family.

🌀 I prefer weed people. Cocaine people never seem to realize they're going to want cocaine...
Cocaine people: "It's 1am. We need to find blow."
Weed people: "It's 1am. We need to find a taco bell that's open."

🅼🅰🆃🆃 💎 🆁🆄🅱🆈 @mattruby

I’m a little Korean boy now

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Misguided Meditation debuts!

Thanks to everyone who came out to the debut performance of Misguided Meditation last week. The show went great and it was awesome to see some Rubesletter readers there. More performances to come in NYC and hopefully elsewhere too. Just email me to get notified.

🅼🅰🆃🆃 💎 🆁🆄🅱🆈 @mattruby

The debut performance of Misguided Meditation was amazing! (It's my meditative comedy show about death, therapy, and psychedelics mixed with a live ambient soundscape from @StevenPestana). Another one coming soon. DM me if you’d like to get notified.

5-spotted

1) What kind of jeans are in right now? (Haley Nahman)

Set foot in any store where denim is sold, and you’ll find among the racks a panoply of silhouettes and styles: mom, dad, boyfriend, girlfriend, skater, stovepipe, 1990s, sculpted, cigarette, puddle, patchwork, contrast, slim, split. The question of what’s stylish may be better formulated in the negative: What isn’t?…
Such a landscape, where nothing is “in” or “out” so much as chosen or not, presents some clear wins for fashion as a form of self-expression. But what else may the smorgasbord of jeans being sold today say about this moment in history? Denim, after all, has always been a cultural weather vane.

2) Write for One Person. (David Perell)

I heard that Warren Buffett addresses the early drafts of his shareholder letters to his sister, Dorothy.
Once he finishes it, he replaces her name with "Shareholders."
The lesson: Writing for a huge audience is a fast track to getting writer's block, so write for one person instead.

3) ‘Mama Ayahuasca told me to invest in crypto.’ (Jules Evans)

I have the same attitude to them as I do to other religious movements — sceptical ecstasy. No religion is perfect, they are probably all wrong in their cosmic predictions and all have flaws and shadow sides. That's why I have, as it were, a balanced portfolio of religious ideas, rather than going 'all in' on one particular religion.
We can nurture the same sort of ‘sceptical ecstasy’ with crypto and psychedelics: be open to the new, have hope that things can and do get better, but don’t let your animal spirits carry you away completely. Or plant spirits.

4) The Black Lady Therapist trope. (Aisha Harris)

The Black Lady Therapist is a trope I named a few years ago in an essay for Slate, after observing Hollywood's growing trend of casting Black actresses to play psychiatrists/counselors to (mostly) white protagonists. The performers are usually older, established character actors inhabiting bit roles for an episode or two (sometimes more); rarely does the audience know anything about this therapist beyond their name – they serve the narrative only as a vessel through which the protagonist can reach an epiphany about whatever trauma or personal conundrum they are dealing with at the moment. The B.L.T. is the sounding board and sage giver of advice, a 21st century incarnation of the broader and much older Black Best Friend trope.

5) David Byrne on the importance of collective rituals:

CBS Sunday Morning 🌞 @CBSSunday

Musician David Byrne discusses the importance of collective rituals, such as concerts, which have been denied us during the pandemic lockdown, and how their return is part of our healing. cbsn.ws/3ALlhUb

Thanks for being a read-to-the-ender!

-Matt

The end stuff

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About the Rubesletter: Weekly musings from a standup comedian and startup veteran. If you like my comedy or writing, if you dig tech, politics, art, wellness, & pop culture, if you enjoy smart/nuanced takes & hate BS, if you’d like me to turn you on to other people making cool stuff, then subscribe.

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