Probably! I'm still getting jokes on reread now, in my thirties. But if you don't have any gen X brits who are also Pterry fans close to hand, may I present to you L-space? It's quite an older site, built out of the old Usenet alt.fan.pratchett listservs, and it includes quite a lot of helpful metadata on everything Pratchett published.
In particular, L-Space contains the Annotated Pratchett File, being a repository of all the references anyone could suss out from about 1992 on, usually verified by asking Pterry himself if he'd meant to do that or not. There is also a set of annotations available in a crowd-sourced format through the Lspace Wiki.
Annotations make getting the jokes funnier and you get to learn more about the layers of meaning in the work, plus you can chase weird rabbit trails off them in your own time. I highly recommend anyone who enjoys Discworld and knowing stuff spend some quality time with one of the book annotations at some point.