Trae Crowder and Jessi Klein

Comedian and writer Jessi Klein (Big Mouth, Inside Amy Schumer, I’ll Show Myself Out ) and comedian Trae Crowder ( The Liberal Redneck Manifesto , Trash Daddy ) join Jameela Jamil to unpack a lifetime of exquisitely timed social misfires, celebrity encounters gone wrong, and the unique horror of realizing you may have accidentally discouraged a bunch of people who later became extremely famous. Jessi confesses to being Clare Danes’ first hater, gently warning a pre- My So-Called Life middle schooler that acting might not be a practical career choice, then doubling down years later by encouraging Mark Ronson to stay in college instead of becoming a DJ. Things only escalate from there, including an Ethan Hawke missed connection that still haunts her soul. Trae shares his own catalogue of humiliation, from confidently announcing “I was on Bill Maher” to Tim Robbins with no follow-up, to screaming his friend GABE’s name across a room full of A-list celebrities, to destroying his kids’ new drone in front of an elderly father-in-law who immediately climbs a tree to retrieve it while silently judging him. Along the way, Jameela recounts freezing into a full-body malfunction while meeting Whitney Cummings, and why sometimes the worst part of a sympathetic interaction is knowing you’ll definitely have to see that person again. No villains. No winners. Just deeply relatable micro-humiliations, permanent psychic damage, and the long tail of regret. Jessi Klein’s book I’ll Show Myself Out is available now, and she co-hosts the podcast Here to Make Friends . Trae Crowder’s stand-up special Trash Daddy is streaming on YouTube, and his books The Liberal Redneck Manifesto and Round Here and Over Yonder are out now. Jameela's Substack is A Low Desire To Please , you can also find her on Instagram , TikTok and YouTube . Our consulting producer is Colin Anderson . Wrong Turns was created and produced by Jameela Jamil and Stewart Bailey. Hosted on Acast. See acast.com/privacy for more information.

You can listen to Trae Crowder and Jessi Klein online on Radio and Podcast. Open the player on this page to stream the available audio.

Trae Crowder and Jessi Klein is an episode from I Weigh with Jameela Jamil by Jameela Jamil.

This episode is 44:34 long.

This episode was published on Jan 15, 2026.

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