I'd actually even go so far as to say 5 is better from start to finish than 3 from start to finish. At World's End has some amazing sequences, the maelstrom battle being one of the best of the franchise, but there are also some sequences that get muddied by the overly convoluted plot of people making deals with each other and figuring out who's playing who, etc. Pirates 5 has a much more straight forward story and you get a consistent experience from start to finish. My issue with 5 is the portrayal of Jack.
Here's how I'd rank the franchise.
1. Curse of the Black Pearl - This movie is just great from start to finish. The story is straight forward and feels like a classic adventure based around pirates of the era, the characters are written and acted wonderfully, and the music is fantastic.
2. Dead Man's Chest - This movie does a great job of continuing the overall tonal quality of Curse while introducing more supernatural and mythical elements. Davy Jones is an incredible new character with an amazing performance. The story is a bit more complex than Curse, which does hurt it at times.
3. Dead Men Tell No Tales - This movie was wise to go back to a simpler story like Curse, however, it goes so far as to be almost identical in the supernatural element. The new characters were interesting end entertaining and the returning characters were used quite well. With it being a movie about Pirates, the inclusion of adventures and battles at see was a big leap forward after On Stranger Tides and really made this entry feel like it belongs in the series. For me, this movie is brought down by the manner with which a down on his luck Jack Sparrow was portrayed. The drunken aspects to him were over the top with a lot of ridiculous dialogue and jokes that just don't work. It feels like the greatest departure from his character in the entire series.
4. At World's End - Like Dead Man's Chest, this film did a great job of keeping the feel of it's predecessors and the characters continued to deliver quality performances. The action sequences are fantastic, the music adds some great new themes. If this movie had more time in the writing room, I think the end product may have been much better, but writing on the go really hurt it and the plot is really hard to follow at times. It's easier on repeat viewings, but I still remember walking out of my first viewing in a very confused state and not really knowing how I felt about it.
5. On Strangers Tides - I rank this last as a Pirates movie because it honestly feels more like a Captain Jack Sparrow solo film that didn't commit to being that type of film, and in trying to work other Pirate characters and plot into the film, it weakens the overall film. It lacks sea battles, the music is heavily recycled, the new characters are lacking and even some of the call back characters aren't their best. As far as Jack Sparrow goes, I love this movie for the spotlight it puts on him and he is still very much classic Jack. The impostor sword fight at the beginning of the film is great, both in choreography and score, and I wish the franchise had more of those 1 on 1 type duels where you just focus on the fight and not cut back and forth between that and a larger battle going on elsewhere.
I disagree, I would still put the first 3 movies above the 2 that came after, and while I do agree that CotBP is the best of the franchise I personally enjoy Dead Man's Chest a lot more. That movie had so many things going for it, an amazing villain realized with groundbreaking CGI that holds up to this day, amazing set pieces, beautiful locations, memorable fight scenes, arguably the best sea monster in cinema and a banger soundtrack.
At World's End gets really messy and sluggish at times, which is no surprise when one takes into account they were still writing the 2nd and 3rd movies when they began filming but it has way better action and character moments than OST or DMTNT. Not to mention so many iconic scenes, the opening with Hoist the Colours, Elizabeth's speech, Up is Down, the entirety of the maelstrom fight, which is still the best fight in the entire franchise.
The first 3 movies feel like a cohesive experience, sometimes messy for sure but **** Verbinski brought an undeniable style and tone to the Pirates movies that's completely missing in what came after.
OST feels the closest to the first 3, Johnny Depp is still at the top of his game as Jack, there's really amazing character moments, nice additions to the world with the mermaids and beautiful locations but the movie completely fails at being a Pirates movie once they get on the island, it begins to feel closer to Indiana Jones.
The priest and mermaid romance subplot felt like something the studio demanded because it felt so out of place and rushed, it sticks out like a sore thumb, I really didn't like it.
Ian McShane was such good casting as Blackbeard but absolutely wasted as a character, whatever villain they had lined up after Davy Jones had BIG shoes to fill but it feels like they didn't even try with Blackbeard, the movie instead treats Penelope Cruz's Angelica as Jack's villain and she too is an unremarkable character, to the point they completely dropped her whole arc and the voodoo doll plot in DMTNT.
Dead Men Tell No Tales to me is the one that feels the least like a PoTC movie, it has that modern over sharpened, fake, CGI look of every other Marvel and fantasy movie that has come out in the past 10 years. Johnny Depp lost the ability to portray Jack, likely because of what was going on in his private life while he was filming it and it comes across on screen.
Not only that but it's the first time they brought a new writer in and it's clear they had no idea how to write Jack or what the established lore was, so many blatant retcons and plot holes that break the continuation of the previous movies, especially in regards to the Dutchman and the compass. And how Jack reacted to the miniature Pearl sinking? His beloved ship, his freedom? That's the best example of how badly the script fails Jack and the entire franchise as a whole.
I guess Salazar was a better villain than Blackbeard, his ship was cool but Javier Bardem was wasted as well, he spends the whole movie basically grunting "Jag Sbarro" lol and while it was cool to see Will and Elizabeth return for some cameos it did feel tacked on and turned the Dutchman into a curse and not a job from Calypso. Let's not get started on the post credits scene, the trident supposedly broke all sea curses but "Somehow Davy Jones returned." The entire script is a mess.