Henry Oliver on Measure for Measure, Late Bloomers, and the Smartest Writers in English

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Henry Oliver is the preeminent literary critic for non-literary nerds. His Substack, The Common Reader, has thousands of subscribers drawn in by Henry's conviction that great literature is where ideas "walk and talk amongst the mess of the real world" in a way no other discipline can match. Tyler, who has called Henry's book Second Act "one of the very best books written on talent," sat down with him to compare readings of Measure for Measure and range across English literature more broadly.

Tyler and Henry trade rival readings of the play, debate whether Isabella secretly seduces Angelo, argue over whether the Duke's proposal is closer to liberation or enslavement, trace the play's connections to The Merchant of Venice and The Rape of Lucrece, assess the parallels to James I, weigh whether it's a Girardian play (Oliver: emphatically not), and parse exactly what Isabella means when she says "I did yield to him," before turning to the best way to consume Shakespeare, what Jane Austen took from Adam Smith, why Swift may be the most practically intelligent writer in English, how advertising really works and why most of it doesn't, which works in English literature are under- and overrated, what makes someone a late bloomer, whether fiction will deal seriously with religion again, whether Ayn Rand's villains are more relevant now than ever, and much more.

Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.

Recorded January 12th, 2026.

This episode was made possible through the support of the John Templeton Foundation.

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Timestamps:

00:00:00 - Intro

00:01:40 - What Shakespeare is really saying in Measure for Measure

00:29:17 - The best way to consume Shakespeare

00:32:26 - Jane Austen, Adam Smith, and Jonathan Swift

00:39:29 - Advertising that works

00:44:37 - Things that are under- and overrated in literature

00:51:24 - Late bloomers

00:58:36 - Outro

Image Credit: Sam Alburger