Sycophancy: From Shakespeare to AI

·50 min·5 clips

Colin McEnroe explores how AI flatters us, linking ancient sycophancy to today's technology.

The episode begins with host Colin McEnroe introducing sycophancy as a pervasive trend in politics, sports, and AI. He welcomes Mark Parker, co-author of 'Sucking Up, A Brief Consideration of Sycophancy', who discusses historical disgust towards flattery, citing Plutarch and Dante's placement of flatterers in feces. Parker explains how sycophancy damages social fabric by devaluing language. The conversation shifts to literary examples, including Hamlet's interaction with Polonius and Tolkien's Wormtongue in 'The Lord of the Rings'. Virginia Heffernan joins to analyze modern sycophancy in the White House, referencing Michael Cohen's description of Trump's manipulative tactics. Clips of Steve Witkoff and Pam Bondi flattering Trump illustrate extreme, prolonged praise. Heffernan notes the fear and survival strategies behind such behavior. The final segment features Maliha Alahani, who defines AI sycophancy as models aligning with users' beliefs over evidence, citing studies where AI affirmed harmful actions. She discusses the need for AI literacy and designing systems that introduce positive friction to challenge users. The episode concludes with a musical outro about flattery.

As heard by us

A reflective look at sycophancy as power, praise, and AI-enabled flattery.

The episode treats sycophancy as a habit that runs through praise, power, and performance, moving from presidents and athletes to AI. It brings back Mark Parker, who also appeared on the show in 2017, and uses that return to keep the discussion anchored while it opens out into…

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If you want a show about sycophancy, from Trump to AI, start here.

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