So what exactly is an asshole? Is it a settled character type, or just a way of behaving that anyone might fall into on a bad day? Why does asshole behavior provoke us as it does, and why does it seem so much harder to resist now than it once was? If assholes are produced by social conditions (and they appear to be), what conditions produce them, and which ones might produce fewer?

This episode takes Aaron James’s 2012 bestseller, Assholes: A Theory, as its central provocation. James defines the asshole as someone (almost always a man) who “systematically allows himself to enjoy special advantages in interpersonal relations out of an entrenched sense of entitlement that immunizes him against the complaints of other people.” The HBS co-hosts work with this definition and push on it where it falls short. Bob makes the case that contemporary capitalism, supercharged by the compare-and-contrast machinery of social media, has transfigured a vice into a virtue: in our current moment, assholery is increasingly mistaken for strength. Jen draws on Rousseau’s distinction between amour de soi and amour-propre to ask what social conditions cultivate the asshole disposition. And Leigh asks what we can do, practically, in our classrooms and in our daily encounters, to make environments less hospitable to assholes in the first place.

Grab a drink and join us as we try to figure out what makes an asshole an asshole — and what, if anything, can be done about the apparent abundance of them in our current moment.

This week’s jukebox picks:

From Jen: “Goodbye, Earl” by The Chicks
From Leigh: “Yakety Sax” by Boots Randolph
From Bob: “Asshole” by Dennis Leary

In this episode, we discuss the following thinkers, ideas, texts, etc.:

• Aaron James, Assholes: A Theory 
• The “Karen” as a contemporary type of asshole
• The sovereign citizen movement
• The manosphere and figures like Andrew Tate
• QAnon
• The “Am I the Asshole?” subreddit
• The American Association of University Professors (AAUP) and the defense of academic freedom
• Aristotle, Nicomachean Ethics — particularly the doctrine of the mean (Book II)
• Virtue ethics (Stanford Encyclopedia of Philosophy)
• Jean-Jacques Rousseau and his distinction between amour de soi (self-love / self-care) and amour-propre 
• Jean-Jacques Rousseau, The Confessions 
• The Cartesian subject and the Enlightenment conception of the self
• Ayn Rand and Objectivism 
• Stoicism 
• Cancel culture 
• John Dewey, Democracy and Education 
• Michelle Obama, “When they go low, we go high” (Democratic National Convention speech, July 25, 2016)
• The Scott Jennings / Adam Mockler CNN F-bomb incident (April 30, 2026, NewsNight with Abby Phillip)