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

Conversations with Tyler

Education, Society & Culture

4.8 • 2.6K Ratings

🗓️ 4 March 2026

⏱️ 59 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 vi deo 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

Transcript

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0:00.0	Hi, listeners. This is Tyler. We're hosting our next Conversations with Tyler listener meetup at the Vault Gallery in Chicago, Illinois, on Friday, April 10th.
0:15.2	This is your chance to meet me and the members of the Conversations with Tyler team to connect with fellow listeners
0:21.2	and enjoy some great conversation
0:23.4	over light refreshments.
0:25.3	We'll have a Q&A session along with plenty of time
0:28.1	to mix and mingle.
0:29.3	Space is limited and it fills up quickly,
0:31.8	so registration is first come, first served.
0:34.9	Click the link in the show notes to register to attend. Plus ones are welcome. Just be
0:40.1	sure they also register separately using the same link. Hope to see you there.
0:50.0	Conversations with Tyler is produced by the Mercatus Center at George Mason University,
0:55.2	bridging the gap between academic ideas and real-world problems.
0:59.4	Learn more at Mercadis.org.
1:01.6	For a full transcript of every conversation enhanced with helpful links,
1:06.3	visit Conversationswithtyler.com.
1:11.9	Hello, everyone, and welcome back to Conversationswithtyler.com. Hello, everyone, and welcome back to Conversations with Tyler.
1:15.9	Today I am chatting in person with Henry Oliver.
1:19.0	Henry is a research fellow at Mercatus.
1:21.8	He is author of a wonderful book called Second Act about late bloomers, which has been very popular. He writes a wonderful
1:29.0	substack. You can just Google to that, Henry Oliver substack, and he has a new joint substack
1:34.5	with Rebecca Lowe on the pursuit of liberalism. Henry, welcome. Thank you very much for having me.
1:40.6	Now, the premise of this episode is we're going to discuss Shakespeare's Measure for Measure,
	...

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