Funny How: Letters to a Young Comedian

Funny How: Letters to a Young Comedian

How to do comedy forever

Thoughts on success, crowdwork, "the hang," mental health, Mae West, and more.

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Matt Ruby
Apr 08, 2026
∙ Paid

🎙️ The way to keep doing comedy forever is to never stop doing comedy.

🎙️ Comedians make art for people who think they hate art.

🎙️ Many comedians treat their audiences as if they’re morons. In fact, we have a name for them: Millionaires.

🎙️ Riding the subway home after a rough set...

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🎙️ The biggest thing NYC comedy has lost is the hang. I’m talking Kabin on Wednesdays, Rififi after Invite Them Up, The Creek, etc. These were places for comedians of different levels to interact socially IN PERSON. Now, we’ve traded all that for posting “😂😂😂” emojis in each other’s IG comment sections which is no substitute for actual conversation. It’s making comedy feel even more lone wolf-ish – and that’s saying something.

🎙️ The reason I don’t do crowdwork is because I couldn’t care less what people do for a living or how long they’ve been dating. I chose to do standup because I think my ideas are more interesting than Dave in accounting. If I wanted to make insincere small talk with some boring bro, I’d work in a cubicle.

🎙️ A younger comic said I seem pretty mentally healthy for someone who’s done comedy for so long. And I told him the secret to my mental health is my lack of success. There’s simply no way for me to let fame go to my head. Honestly, I would love to let fame go to my head.

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MATT RUBY@mattruby
Literally impossible for a standup comedian to do...so I'm gonna complain about THAT.
4:28 AM · Jan 25, 2026 · 49 Views

🎙️ New comedians: You can try out bits on your friends. Just ask them first. Civilians love that kinda thing. Note: They probably won’t laugh. But just gauge if they 1) even understand your point & 2) think it’s interesting. That’s most of what you’ll get out of an open mic anyway.

🎙️ I like to think about historical figures who would have been great standup comedians. Mae West is definitely up there. Also: Mark Twain, George Bernard Shaw, Yogi Berra, and Oscar Wilde.

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🎙️ Calling hunger “food insecurity” reminds me of that Carlin bit about shell shock vs. PTSD. Maybe if we still said people are “going hungry,” we’d do more to feed ‘em.

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