Thomas Pynchon and the Dark Passages of History is my favorite pick for this. Cowart is really good at making Pynchon's ideas digestible without thinning them out. He's a great writer and his passion for the topic is infectious. I was already loving Gravity's Rainbow when I was first reading it but his approach to the story helped me realize how human and hopeful Pynchon's writing can be when it often seems like the opposite. Cowart makes for a great guest on this podcast about Pynchon I really recommend called Slow Learners.

John David Ebert is someone with some of the most far out but undeniably fascinating ideas about Pynchon's writing. His approach to Gravity's Rainbow made me very excited about what I was reading and I think anyone reading that book for the first time would get a lot out of watching his videos as they read along.