I think he genuinely just doesn’t see anything odd with any of his answers. Think about how different a world he comes from. I have a vaguely positive impression of Jann Wenner because of his association with the golden age Hunter-Thompson era of Rolling Stone and the genuinely good journalism that it still does today. But at the same time, the landscape of what’s permissible behavior from a big white guy in charge has changed so much that we can lose track of how much of an asshole it used to be okay to be.
My sister’s worked in a male-dominated industry for basically her whole life, and now that I’m thinking about it the stories she tells have gradually been transitioning from stuff that’s genuinely horrifying to now being simply upsetting and wrong. I think people who lived during that era are just starting to sound like everyone’s segregation-era grandparents did back in the 90s. I mean, for a lot of his adult life, women basically did live under a segregation system. In one way it’s a good sign for how much progress has been made. Not to excuse him for being an asshole - I’m just saying that it kind of makes sense that the system didn’t filter him out back then, in the way that it would today if he didn’t learn to keep quiet about what he thought about these things.