Today I’m talking with Andy Haynes — stand-up comedian, writer, podcaster, and sharp cultural commentator whose work blends humor, honesty, self-deprecation and social critique. Andy has appeared on Jimmy Fallon, Conan, Comedy Central, Roast Battle, and more. His comedy often explores politics, culture, identity, and the uncomfortable truths we don’t always want to say out loud. In this conversation, we break down how comedy has changed, why some jokes “land” differently today, and how comedians navigate the tension between free speech, responsibility, and backlash. Andy offers a candid look at punching up vs. punching down, the post-Trump comedy landscape, the rise of “culture-war comedy,” and what comics owe their audiences in an era of rapid political polarization.
We also talk about:
✔️ When jokes have real-world consequences
✔️ Why certain groups became “off-limits”
✔️ Comedy’s backlash to wokeness ✔️ How free speech became a political weapon
✔️ What it’s like to perform for veterans, working-class crowds, and online audiences
✔️ Why comedy became more divisive — and whether it can course-correct
✔️ How social media changed what it means to be a comedian today
Andy’s honesty, depth, and perspective make this one of the most insightful conversations I’ve had about the state of comedy, culture, and America.
Tell me in the comments: Do you think comedy changed for better or worse — and why? —
ABOUT ANDY HAYNES Andy is a stand-up comic, writer, and actor based in New York. His credits include Jimmy Fallon, Conan, Comedy Central Presents, The Pete Holmes Show, Adam Ruins Everything, and multiple digital series. He hosts the podcast Beautiful Boys with Mike Cannon. —
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