In the past I have listened to Library of Letourneau's "Bits and Banter" videos on my drive. Northernlion is one of my favourite streamers, and his particular conversation style works much like a radio station in terms of covering interesting topics, humour, callbacks, etc.
Unfortunately fairly recently NL has been on a Counter Strike arc, which means the car-listenability of the Bits and Banter videos has plummeted. Youtube recommended me a Freud lecture by Robert Paul Wolff, which I listened to at home. I liked his style enough that I listened to the entire series of Freud lectures, Marx lectures, and Kant's Critique of Pure Reason lectures on my car rides for the past few weeks.
I love the way he mixes in stories of 20th century philosophy, aspects of his life, the way he's proud of his sons, all while cogently formatting the ideas of several seminal philosophers. I'm not going to pretend like I understood all of it. Freud's were certainly the easiest to understand, then Marx's, which required a bit more mathematical thinking, and then finally Kant's, where I felt completely lost through most of it. To be fair, I was not doing any of the reading. I more listened to these to try and get snippets of ideas, to attempt to gain a cultural understanding of what these philosophers did for thinking at the time, rather than every specificity of their theories.
The lectures were given around the time of the 2016 American elections, which provides an interesting context to the content of the lectures. He describes this, and the connection to the time of the Frankfurt School in the introduction to the Freud lectures.
Last year, Wolff passed away. His chess prodigy son is good friends with Peter Thiel and Warren Buffet, a cruel irony for a Marx scholar. To honour Professor Wolff's memory, I highly recommend listening to his lectures. Below I have linked his first one on Freud.
I can't seem to get a video to embed with an iframe on mataroa, so here is the first lecture.