I haven’t seen the first two. Judge Dredd is okayish, but essentially it’s the same movie as Demolition Man but with inferior directing, special effects, comedy, and pretty much everything. Just watch Demolition Man.
Cabin Boy only had one funny moment in the whole film, and it wasn’t worth it (though that one line, “These pipes are clean!” is now permanently engraved in my brain.)
Why would you want to watch this again?!? Wasn’t it crappy enough the first time?
It all depends.
I tried to watch apocalypse now for several years. When it came on I would turn to it, and invariably fall asleep about half an hour in. So I had a roomie tape it. Unfortunately it was on 4 different tapes as we were poor and didnt have enough space on 1 tape to keep it alltogether.
So I watched it, halaf an hour at a time. It took me totally not understanding a damn thing to figure out that I must not be watching it in order. So we bought a used tape of it, and I watched it half an hour at a time. I would wake up and start from where John turned the tape off when he noticed I was asleep. It still didnt make any fucking sense.
I could have taken the whole movie, cut 75 percent of it away, and made a fantastic movie. Most of it is stultifyingly boring and should not have made it into the film.
And I happen to really enjoy war movies 
Talk about a total waste of time and effort.