I think there's been some counterintuitive championing of both WATERWORLD and THE POSTMAN as being kind of underrated and fun but I think even people who kind of like them should admit that they are not movies that should be expected to be popular with audiences or justify their budgets.
And of course a huge piece of Costner's bankability that allowed him to make those was from ROBIN HOOD PRINCE OF THIEVES which sucks and has to be the least remembered movie in my lifetime to be the #2 movie in the domestic box office for a year
"an entire generation" confused me until further down Chappelle was named. I thought it meant people too young to have been around for PoT and some other movie I wasn't aware of in the last 20 years had been made making fun of it.
Can confirm that my middle schooler was shown Prince of Thieves at a sleepover this past year, and when asked, "Do you know what that's even making fun of?" responded with "Yeeeessss!" But I'm not sure.