If he’s someone that’s normally good at being funny - that is good at finding humorous observations and wording things that get people to laugh - then I’d say he’s messing with you.
I would mess with him right back by acting like I’m very seriously trying to understanding the joke and ask increasingly dumb questions until he realizes that yes, I knew exactly what he was doing. Or a knowing smirk if that’s too much.
(Yes this comment is very revealing about my childhood)
Honestly, I’d be more curious what topics where the media does nail the nuances of. Are there any at all?