Books that investigate the absurd seriously

I'm looking for books that pose a question and then reply, "Okay, but hear me out—" or "Well, let's think about this." Not to put a tinfoil hat on but to push learning and investigation. Sort of like a MythBusters-style read but not exclusively science. Absolutely adore philosophy and literature and want to see someone take the time to seriously analyse something like "last thursday-ism" or talking about Dead Unicorn tropes, where some convention is mocked without actually being a thing to begin with. Loved reading Randall Munroe's books before bed just to tire myself out and want to find more. The 2016 documentary 'Tickled' also falls into this category, where it starts off as a fluff piece about the strangeness of a professional tickling competition, but the secrecy of it makes the team dig further. Competitive tickling organisation makes you ask, "How far does this rabbit hole go?" I want to find someone who gets posed strange or absurd questions and actually puts in effort to find a real answer to them.