The Simpsons Writer Who Had to Teach Himself to Be Funny | Brent Forrester
October 20, 2026 · 56 min
Why listen
A veteran comedy writer explains how he taught himself to be funny by reverse-engineering jokes.
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In this episode
- A practical formula for writing jokes that actually land
- Why silly and funny are not the same thing
- What made the classic Simpsons and Office writers rooms work
- An honest debate on whether AI can replace human writers
About this episode
Brent Forrester has written for The Simpsons, The Office, King of the Hill, and The Ben Stiller Show.
So naturally, he says he wasn't born funny.
Brent joins Jay to explain how he actually taught himself comedy by obsessively studying jokes, breaking them apart, and figuring out why they worked — a process that eventually landed him in some of the greatest comedy writers' rooms in television history.
They talk about writing during the classic years of The Simpsons, what made The Office work, Judd Apatow and The Ben Stiller Show, why some brilliant comedy writers aren't particularly funny in person, and whether being funny is something you can actually learn.
Then things get existential.
Can AI replace writers? What happens to art when there's no human being behind it? Why should anyone keep writing when a computer can generate something in seconds?
Brent and Jay don't completely agree.
They also get into the mechanics of writing jokes, why beginning comedy writers should start with sketches, Brent's formula for funny, why "silly isn't funny," writing characters who are broken, and why Brent is now betting on YouTube instead of waiting for Hollywood to give him permission to make something.
Basically, two comedy writers attempt to explain comedy.
Which seems like a terrible idea.
Enjoy.Subscribe to Don't Be Alone with Jay Kogen for more conversations with writers, comedians, actors, creators, and thought leaders exploring life, creativity, politics, and the human experience.
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About Don't Be Alone with Jay Kogen
Don’t Be Alone with Jay Kogen is a comedy/advice podcast trying to fight the isolation of modern life. Each episode, Award winning TV writer/comedian/philosopher Jay Kogen has a conversation with a friend about how to solve the problems on Jay’s mind.
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