About Funny How: Letters to a Young Comedian

“Love this!”
-Gary Gulman

-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 newer (and experienced) comics about the art and craft of doing standup – mostly from comedy legends like Jerry Seinfeld, George Carlin, Steve Martin, etc.

I know, 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.

“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.

Joe Pesci Goodfellas GIF

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. So let’s see if we can’t run that idea back in this new age of newsletters.

Every Monday/Wednesday/Friday, I’ll post another edition. I’m going to 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 to focus on).

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

In the meanwhile, here’s some of my standup:

Subscribe to Funny How: Letters to a Young Comedian

Comic Matt Ruby offers standup comedy philosophy, advice, and inspirational quotes from great comedians. Some praise for posts here...Judd Apatow: "Great." Gary Gulman: “Love this!”


Comedian/writer/filmmaker. Creator of Vooza. NYC.