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Cass was in top form, and so we went on for almost two hours.  In his Substack he described it as “The most fun interview I have ever done.”  Here is the audio, video, and transcript.  Here is part of the episode summary:

Tyler and Cass discuss whether liberalism is self-undermining or simply vulnerable to illiberal forces, the tensions in how a liberal immigration regime would work, whether new generations of liberal thinkers are emerging, if Derek Parfit counts as a liberal, Mill’s liberal wokeism, the allure of Mises’ “cranky enthusiasm for freedom,” whether the central claim of The Road to Serfdom holds up, how to blend indigenous rights with liberal thought, whether AIs should have First Amendment protections, the argument for establishing a right not to be manipulated, better remedies for low-grade libel, whether we should have trials run by AI, how Bob Dylan embodies liberal freedom, Cass’ next book about animal rights, and more.

I will reproduce the section Cass pulled for his own Substack:

COWEN: Now, we started with the topic of liberalism. How is it you think about or characterize the liberalism of Bob Dylan?

SUNSTEIN: Bob Dylan is a liberal. His liberalism is captured in the line, “He not busy being born is busy dying.” I hope he’s immortal, but if anything is on his epigraph, that would be a good candidate.

The notion of self-invention, of freedom, is central to basically everything. His refusal to keep singing the same song — you can hear him talking about it in some of the interviews. He said, “I could do that. I could just do that forever. I knew how they’d react.” He said, “What’s that about?” He said, “I needed to do something else.” But of course, the line, “I needed to do something else” — that’s my line. How he would put it would be much more vivid and surprising than that.

His “Like a Rolling Stone” is an anthem of freedom. I heard it, actually, in concert a few years ago. It was a great performance. It wasn’t young, but it was a great performance. The audience went wild when he did “Like a Rolling Stone.” That was the final song. It was the encore. It wasn’t just because it was the greatest rock song ever written. It was because of how he did it. I thought, “What’s going on in this song? Why is everyone exhilarated?” The song, which he described when he wrote it as vomit, hatred directed at somewhere that was real — it wasn’t that, or it was a little bit that, but it was a song of liberty.

“How does it feel to be on your own with no direction home, like a complete unknown, like a rolling stone?” Everyone felt like they were flying. He makes that — “Like a Rolling Stone” — be a song of freedom. If you look at his angry songs — “Positively 4th Street” — there’s a freedom in being, of course, uninhibited, able to say things, but also a freedom of disconnection.

When he’s asked why did he change his name, I have an account of why he actually did. I think he gave it exactly once, but in his more characteristic way, he said, “This is America. You can change your name.” Then he said, “I was born. I didn’t think I was born with the right name. I could make it up. I could say that sounds more like I was.”

Making rootlessness not be a curse, but instead something that is . . . the word joy is too clichéd for Dylan. If you look at his love songs, like “If You See Her, Say Hello,” which isn’t one of my favorites, but it’s good. There’s a connection with the one he loved, who got away, but you can feel the sense of freedom.

COWEN: “Visions of Johanna”?

SUNSTEIN: Yes, completely. He’s torn. That has the great opening line. “Ain’t it just like the night to play tricks When you’re trying to be so quiet?” Did Yeats write better lines than that? Probably, but he was Yeats.

COWEN: Blood on the Tracks — a liberal album?

SUNSTEIN: Oh, yes.

COWEN: How would you express that?

SUNSTEIN: Well, I’m thinking “Buckets of Rain” is the closing song. Right before that, there’s a song, “You’re Gonna Make Me Lonesome When You Go.” That’s it, which is, I think, one of his greatest songs. That’s a liberal song of freedom and separation, that she’s going, but he’s going to see her everywhere, and there’s smiling at impermanence. That is a big liberal theme — smiling at impermanence — because impermanence makes things not routine and also makes for freedom.

COWEN: “Idiot Wind” is the angry song of the batch, right?

SUNSTEIN: Yes, it’s pretty mad. He said about that song, “I don’t know why people like it. There’s so much sadness and distress in it.”

COWEN: Do you see your own liberalism or just yourself in the liberalism of Bob Dylan?

SUNSTEIN: I think so.

COWEN: Reinventing yourself, not quite wanting to be pinned down, doing a lot of stuff.

SUNSTEIN: He likes, I think, abandoning and going on to something that’s very different. I wish I’d gone electric or had some equivalent of that. But doing something quite different — I do share a little bit with him. I like it when I think something I thought was wrong. I now am very enthusiastic about the Austrian economists and Hayek. I’ve always admired them, of course, but I didn’t feel that they were on my team. Now I feel I’ve gone to their team. I don’t feel ashamed that I was wrong before. I feel excited that I’m less wrong now.

Definitely recommended, I could have pulled out many other parts as well.  Again, I am happy to recommend Cass’s new book Liberalism: In Defense of Freedom.