Like, I wholeheartedly agree, he doesn't achieve good interviews by the quality of his questions.
Except... that he kind of does, in a weird way. Experts on the show are happy to use those questions as a launching point to correct whatever incorrect assumptions he had in asking it.
He's very good at getting people to open up and talk. Perhaps dumb questions play a role in that? Perhaps they make people feel comfortable by validating their expert status in the room or something, I don't know. But I do know that it seems to work. I also know he's a comedian. Comedy is fundamentally a weirdly manipulative art form... You carefully craft a set of jokes and then practice over and over again to make it feel like an organic, albeit funny conversation. Every little pause, intonation, turn of phrase, it's all intentional. So, being that he is a practiced comedian, it's possible some of that interview style is pretty intentional too.