About Funny How: Letters to a Young Comedian

“Love this!”
-Gary Gulman

“Great.”
-Judd Apatow

Hey, I’m Matt Ruby and this is my newsletter about doing standup comedy. It’s inspired by Rilke's Letters to a Young Poet. Well, as inspired as you can be by something you’ve never read. It’s advice for new (and veteran) comics about the art and craft of doing standup – mostly from comedy legends like Jerry Seinfeld, George Carlin, Steve Martin, etc.

Why should I listen to you? You don’t have to. But here’s my latest standup special if you want a taste of my style of standup:

And I know trying to teach standup is like skiing about architecture or whatever. But that attitude is why there’s so little good info out there for newer comics. I’m just writing the kinda stuff I woulda liked to read when I was first starting out.

If you want some background on me: Here’s my comedy site and some links to more of my stuff. I also write a weekly newsletter called the Rubesletter about tech, politics, comedy, culture, etc.

“But you’re not big or famous. Why should we listen to you?” Well, who else ya gonna listen to? Also: If I was big/famous, I probably wouldn’t write this because I’d be on a private jet yelling at my publicist. Sometimes you gotta drink water from the well you find.

Also, I did spend years writing a blog about the art of standup called Sandpaper Suit and it was pretty popular among comics back when blogs were a thing.

Timing: Every Monday/Wednesday/Friday, I send another email. I deal mostly with evergreen stuff about the actual craft of writing jokes, going onstage, and making a roomful of people laugh (as opposed to algorithm trickery and/or whatever else Zuckerberg/the Chinese government wants us all to focus on).

If you dig it, please post about it, tell a friend, and/or subscribe.

In the meanwhile, here are all my standup specials: