789 The 25 Greatest Books of All Time (with Mike Palindrome) | My Last Book with Cass Sunstein

The History of Literature

Jacke Wilson

History, Arts, Books

4.6 • 1.3K Ratings

🗓️ 2 April 2026

⏱️ 73 minutes

🔗️ Recording | iTunes | RSS

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Summary

In 2025, Jacke began a countdown of the top 25 greatest books of all time, as part of a series called "25 for 25." In this episode, Jacke reveals the #2 and #1 entries on the list. Then Mike Palindrome, longtime friend and President of the Literature Supporters Club, joins Jacke to discuss the books chosen, the relative merits of the list, and propose some alternatives. PLUS Cass Sunstein (How to Become Famous: Lost Einsteins, Forgotten Superstars, and How the Beatles Came to Be) stops by to discuss his choice for the last book he will ever read. The music in this episode is by Gabriel Ruiz-Bernal. Learn more at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠gabrielruizbernal.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Help support the show at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠patreon.com/literature⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠or ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠historyofliterature.com/donate⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. The History of Literature Podcast is a member of Lit Hub Radio and the Podglomerate Network. Learn more at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠thepodglomerate.com/historyofliterature⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	The History of Literature Podcast is a member of the Podglomerate Network and Lit Hub Radio.
0:08.8	I'm Alan and I'm Sean and together we host the prancing pony podcast.
0:12.9	Every week I explore Middle Earth with Sean or with other co-hosts lately with in-depth analysis and plenty of nerd humor.
0:18.5	From The Hobbit to the Lord of the Rings and more,
0:21.1	it's a great way for first timers to experience J.R.R.R. Tolkien's captivating world. And for
0:25.7	long-time fans, it's a deep dive into their favorite stories. So if you're ready to take
0:29.6	the next step into the most beloved world in fantasy literature and become a part of a vibrant
0:34.5	active community of listeners, then look for The Prancing Pony
0:37.9	Podcast, wherever you listen.
0:40.1	Hello, the 25 greatest books of all time.
0:43.4	What are we even doing?
0:45.4	Mike Pallandrum joins us for a discussion today on the history of literature.
0:50.3	Music literature. Okay, here we go. Welcome to the podcast. I'm Jack Wilson. It's nice to have you here.
1:07.8	It was a great idea when I started. It was 2025. That's a couple of nice
1:13.4	round numbers. And halfway through the year, I thought, let's do something to celebrate. How about
1:18.4	25 books? The best 25 books of all time. The greats. Why not? Well, here's a reason why not.
1:27.0	Who gets to choose such a list? Me?
1:30.6	I would ordinarily rise to the challenge, but I thought, well, is that really great for listeners
1:35.6	where they get to hear all about Boswell's Life of Johnson again, and James Joyce's
1:41.6	the dead again, and on and on. Me, me, me, me, me, me. Check off.
1:47.6	You know all my favorites. So I thought, well, I'll find a list. Find one that others have done.
1:56.3	But what list do you choose? Any kind of selection is going to be subjective. So I go through all of this
	...

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