Here is the audio, video, and transcript.  In the first half of the episode we discuss Shakespeare’s Measure for Measure, and then move on to other topics.  Here is the episode 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.

Excerpt:

COWEN: Now, before doing your current work, you were in advertising for almost a decade. How do you feel that work in advertising has shaped how you read literature?

OLIVER: [laughs] I try to keep them very separate. I try not to let advertising—

COWEN: You try, but I’m sure you fail.

OLIVER: —pollute my readings of literature.

COWEN: Why is it a pollution?

OLIVER: Because advertising is not a great art, and to apply the principles of advertising to literature would be a diminishment.

COWEN: You don’t have to apply the principles. Advertising gives you insight into what people value, how people respond, and that’s also a part of literature.

OLIVER: It is if you take advertising not to mean headlines and banner ads and things like that, but to mean the calling of attention to some particular thing of importance. You can see that a lot of the great writers were very good advertisers of their own work, of their own ideas.

COWEN: Swift in particular.

OLIVER: Swift is very, very good at advertising. If you wanted to be obtuse, you could reframe his whole career as an exercise in lobbying and PR, and realize that no one’s ever been as good at it as he was.

COWEN: So, your favorite authors are the ones who are best at advertising is what you’re now telling us.

OLIVER: I have a very catholic view of literature, and I admire those writers who are practical and can do a lot of different things. I love Samuel Johnson, and one reason is that he can write a sermon, a legal opinion, an advert—almost anything you want. I think the literary talent can often be turned to those multiple uses.

COWEN: Why isn’t there more creativity in advertising? So much of it, to me, seems stupid and boring.

OLIVER: Yes.

COWEN: You would think, well, if they had a clever ad that people would talk about, it would be better, but that doesn’t happen. Is it a market failure, or it’s actually more or less optimal?

OLIVER: I don’t think it’s optimal. We don’t know how well advertising works, and we’re still impeded in that because of the laws about who you can and cannot target on the internet. I think most people would actually be surprised, if they went into an advertising agency, to learn just how poorly we can target people. Everyone thinks they’re being targeted all the time, but being followed by a toaster advert is really quite basic, and everyone uses the same toaster example because everyone’s being followed by the same bloody toaster. That’s not targeting.

I think they’ve been taken over by bad ideas. There are two competing schools of advertising. One of them is the hard sell, where you put a lot of information and facts, and you name the product a lot. “Buy this aspirin. It cures headaches three times quicker than other brands. We did a study—38 percent of people . . .” And you just hammer it all the time.

The other advertising school is image-based. Arthur Rubicam wrote those wonderful Steinway adverts. The instrument of the immortals. Have you brought great music into your home? The woman in the dress at the piano. You’re buying a whole mood or a vibe. The peak of that is like the tiger on the Frosty cereal packet. You don’t need words. Or the Marlboro Man—you buy these cigarettes. You’re going to look like that cowboy in that shirt, and you’re going to smoke. You’re going to feel like a man, and it’s just going to be great. Coors Light does that now.

Then there was this terrible, terrible thing called the Creative Revolution in the 1960s, where supposedly—this is like the modernism of advertising.

Definitely recommended, and do get out your copy of the Shakespeare.