I've seen some of Flint Dibble's stuff on social media. He does seem like the kind of person one needs for that job.
I think most academics, and I don't know if they're wrong about this, shy away from that sort of engagment because it really does need a particular set of skills. Like, you need to be carrying a very wide arsenal of facts with you because it's so easy for someone to shoot out some bit of information you didn't know and, when you're in a live interview, it's much harder to look up some citations for why they're wrong. I think that's the thing that would terrify me about doing that sort of thing: I'd like to be the sort of person who could do it, but I worry I'd flail when people started shooting facts at me about things I know I don't truly know well enough to contradict them (because the "pop culture knowledge of the past" stuff is so much broader than most individual academics actually look at, myself included and I'm a relatively broad-brush historian).