Imagine someone like this British comedian woman, unfortunately I forgot her name, who (on purpose) asks these really absurd or stupid questions during interviews with scientists etc. in an interview with Trump.
Like when he mentions this “Democrats because many people don’t know dumb ends with a B” and then going like “Wow, I never new that, you’re so smart. Please explain how you came up with that”.
I guess he wouldn’t be defensive about it because he got called smart and really expose himself.
I think you’re thinking of Philomena Cunk or however it’s written.
I think Dan Toomey / Good Work could also work.
I also think the underlying idea of your post is a great way of thinking about it: clearly traditional interviews don’t work because he is finding ways to circumvent criticism. The best way we could do it is non-traditional interviews.