Hi! I just watched the first four movies for the first time! I saw the 5th movie in the theaters but I don't really remember it so I am going to watch that one next!
Pirates of the Caribbean has always been one of my favorite attractions at Disneyland! SOMETIMES, I would even call it my number one favorite. I remember when I first went on that ride, I went on it like 4 times in row. I finally decided to watch the movies and they were pretty good!
My favorite: I can not decide between the 1st, 2nd and 4th (basically all of them except for the 3rd).
Least favorite: The third movie (At World's End) was definitely my least favorite because I had no Idea what was going on. After staring at the screen for 2 hours and 49 minutes without knowing what was happening in the film, I had to look up the plot. Maybe if I understood it better or watched it again but paying more attention, I'd like it more.
I think that when watching the movies, I focused most on Jack Sparrow's character as the center of the movies which is what I think determined my ranking for the films. In other words, my ranking of each movie was kind of based around Captain Jack Sparrow in that movie ( if that makes sense). That might have been why I liked Pirates of the Caribbean: On Stranger Tides (the 4th) so much. I enjoyed the first two also though so it is very difficult to pick a favorite. Hopefully Pirates of the Caribbean: Dead Men Tell No Tales (the 5h) is good :).
Also, about the 6th one coming out. I was a fan of Margot Robbie as Harley Quinn and I think she'll do well in the pirate role. However, I am definitely kind of upset about the removal of the original main character. I'm glad that they are choosing Margot and not someone else random, but again, I don't think the original character can be surpassed and it is very disappointing that Jack Sparrow will not return to be the main character of the next movie.
On a final note, I enjoyed the films :D