@EricLawton Another one for your list: Anything by David Runciman (historian of political philosophy).
He's done a number of different podcasts through the LRB (London Review of Books). Present venture is Past Present Future. Also a few appearances on IQ2 as noted, some YouTube appearances, and a few standalone single-episode lectures (climate change, and IIRC conspiracy theories).
He's one of those sort-of-dry Brit types, but is incredibly insightful on almost everything he covers. Some of that is material I've some expertise in myself, and I'm impressed that he doesn't appear obviously wrong, often brings new concepts to bear for me, and where our knowledge overlaps he frequently strongly reinforces and supports my own interpretations and conclusions.
An example of that latter was an episode covering Max Weber where he deconstructs (and corrects popular misconceptions of) Weber's so-called "monopoly on violence" definition. (Spoiler alert: that's the wrong interpretation). I'd reached similar conclusions a year or two before hearing the episode, and listening to Runciman spell that out was both illuminating and validating.
I hesitate to mention Rand, but his coverage of her book(s)? (I know he did A.S., I think he mentions but doesn't cover FH in detail). I'd gone through a phase and was quite familiar with the plot and story line. Runciman's anything but a fan, but still gives insights on the book, particularly in the real-world figures her villains are based on. Which was kind of staggering for me to realise. (One I should have known, the economist. The second, the physicist, I hadn't and wouldn't have guessed. I'm avoiding mention to prevent spoilers.)
For someone who finds most current news, tech, and political discussion quite tiresome and dispiriting, he's a breath of fresh air. I'd contrast with someone like Ezra Klein, whom I find quite good, but takes some steeling of myself to get into an episode.