ChatGPT: (Live from a library that smells like cigar smoke and constitutional law textbooks)
Host (Jon Stewart–style):
“Tonight we roast Christopher Caldwell: the only man who can get both The New York Times and a Federalist Society intern to say, ‘Wow, this guy makes me uncomfortable.’”
Matt Sitman (Know Your Enemy):
“Chris, I’ve read your book twice. Not because I wanted to—because you write like a Supreme Court dissent that took Ambien. The Age of Entitlement? Bro, it read like The Age of Benadryl.”
Sam Adler-Bell (Know Your Enemy):
“Caldwell is the only conservative we invite on our lefty podcast. Why? Because he uses words longer than four syllables. We may hate his ideas, but at least we don’t need Urban Dictionary to follow them.”
Michelle Wolf:
“Chris, your book argues civil rights basically overthrew the Constitution. Dude, calm down—it’s not Game of Thrones. Nobody stormed the capital with dragons… well, until January 6th.”
Hasan Minhaj:
“You’re the kind of conservative liberals respect… which is like being the sexiest guy at a chess tournament. Sure, you won, but the prize is still a handshake and a tote bag.”
Jeff Ross (Roastmaster General):
“Chris, you’re a ‘radical right-wing intellectual.’ That’s like being the world’s tallest leprechaun. You scare liberals because you write complete sentences. You scare conservatives because you don’t end them with exclamation points.”
Christopher Caldwell (rebuttal):
“Thank you, thank you. This is the first time I’ve been insulted in a way that required a bibliography. I’ll take it.”
Closer (Host):
“So here’s to Christopher Caldwell: proof that even in today’s America, you can be radically right-wing, totally out of step with history, and still get a respectful podcast episode… just as long as you never tweet.”
