The David Cross Episode
Aug 15, 2026 · 54m
Summary
Ryan Holiday interviews comedian David Cross, exploring how Stoic wisdom intersects with humor, free speech, and social responsibility. They discuss Cross’s new special, the ethics of "punching down," and the danger of rationalizing bad behavior within flawed systems. The conversation also covers parenting, entitlement, and maintaining character amidst modern societal pressures.
Topics discussed
Intro: Italy vacation and sponsors
Guest intro: David Cross and Stoicism
Stoic philosophy in fiction and daily life
Rationalizing slavery and historical complicity
Modern rationalizations: Factory farms and travel
Environmental hypocrisy and 'rolling coal'
Punching down, comedy, and free speech
Privilege and the limits of Stoic advice
Social boundaries and stranger interactions
Sponsors: NetSuite and BetterHelp
Raising kids without spoiling them
Entitlement, character, and bad behavior
Customer service rage and economic fairness
Sponsors: SoFi and Dell
Politics in comedy and audience expectations
Heat waves, AC, and urban planning
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