Is Gen X Funny? Spy, the Daily Show, and more!

Stupid Gen X Tricks

Emmy-winning Daily Show writer Daniel Radosh joins us to talk Spy Magazine, snark, satire, and the fine line between irony and belief.
What made Gen X humor so sharp, so snarky — and so influential? In this episode, we talk with Daniel Radosh, senior writer and producer at The Daily Show, about his career arc from the legendary Spy Magazine to one of the most iconic satire shows in TV history.
We dive into:
How Spy changed magazine journalism forever 📰
Why Gen X humor leaned so hard on irony 😎
The evolution from Suck.com to Gawker, and the generational split
A hilarious Daily Show segment on Chelsea Clinton and diarrhea (yes, really) 💩
Whether humor still has the power to shake people up
And if it's still possible to have your mind blown after 50 🧠✨
Plus: wormholes featuring The Wayback Machine and some unsung woodblock percussion.
Whether you were a Spy reader, a Jon Stewart fan, or just a Gen Xer wondering what happened to our sense of humor, this one’s for you.
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00:00 – Hello Little Rock, Hello Pittsburgh
01:20 – Separated at Birth: Jaws, Dino & Darryl Strawberry
03:40 – Welcome to Stupid Gen X Tricks: Game Changers
05:00 – Our Game-Changing Moments: Spy Magazine & Clinton ‘92
08:30 – Introducing Daniel Radosh
10:00 – Daniel’s Gen X Comedy Career Arc
13:00 – Spy, Snark, and Satire: A New Magazine Era
16:00 – Gen X vs. Millennials: Suck.com vs. Gawker
18:00 – What Made *Spy* So Influential
21:00 – Daily Show, Diarrhea Jokes, and Breaking Jon Stewart
27:00 – Is Satire to Blame for Cynicism?
30:00 – Does the Left Lack a Sense of Humor?
33:00 – Twitter, Humor, and the Age of Overreaction
36:00 – Do Jokes Really Change Power?
38:00 – Can We Still Be Surprised in Our 50s?
42:00 – Radosh on Taylor Swift, 100 gecs & Joyful Discovery
44:00 – Wormholes: The Wayback Machine & Woodblocks
51:00 – Next Time on Stupid Gen X Tricks…