I've tried listening to a whole shit ton of podcasts; I nearly always lose interest within a year.

I re-listen to only two (and re-listen a shit load): The old Pilkington pods (XFM radio recordings, Gervais show, Guide To's, etc.) and TESD. I first starting listening to the Karl stuff around 13 or 14 years ago, still re-listening consistently today. I started listening to TESD after discovering it through CBM probably around 5 years ago, still re-listen to old episodes all the fucking time. TESD and the old Pilkington pods have the same "feel" to me in terms of re-listenability, I've been drinking quite a bit so I can't articulate what that is exactly.

I have no idea if it'll "hold up" in terms of a random future college kid, but I can almost guarantee you it'll hold up for me (which, to be honest, is all I really care about).