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Health warning: if you start trying to work out how the movies fit into that continuity, you will go mad.
I never thought that fitting in most of the movies within the anime's continuity was that hard. Aside from the Victini movie, I Choose You and the upcoming movie, the movies are canon to the anime series. They don't really heavily contradict the anime to the point where they couldn't be set within the anime's continuity at least. I never quite understood the whole debate over whether or not the movies are canon, especially when the anime has made references to some of the movies in the past.
As for the Pikachu Shorts, I think that the first few could fit given that there's at least some reason as to why Pikachu and the other Pokemon are separated from Ash and his friends. I don't know about the rest of the shorts due to how they just have the Pokemon on adventures meeting new Pokemon without any explanation as to where Ash and his friends are.
Movies could be considered like very long fillers, most of the times.
Just like you could grab a filler and slap anywhere in a certain period of the timeline of the current saga, you could slap a movie in certain periods of the timelines of their respective sagas, while looking at the different factors that could determine more or less when they happened (for example, current Pokémon of the gang).
I'm currently rewatching the anime - Ash is about to get his final XY gym badge - and I think it is quite enjoyable. Of course, as others have said, it is quite possible to start with any series as all pokémon apart from Pikachu will be new, and since Brock left, the travel partners will be new for each region as well. I like how the episodes are (often) self-contained stories (unlike for example Naruto where several consecutive episodes may be about essentially the same thing, like one battle, or Naruto trying to learn one specific technique). I don't care that much about most movies, though. Some are good, but many seem to be based on a general formula (legendary pokémon wakes up after having slept for centuries and is attacked by evil humans or by other legendary pokémon, starting an epic battle that threatens the very existence of the universe, until Ash comes in and befriends the legendary pokémon and everything goes back to normal, and then there is some sort of festival and that's it).
@Hidden Mew M14 is canon, but only one version of it (and we don't know which one).
The thing with M14, besides the two versions thing, is that Ash is completely oblivious to who or what Reshiram is in Episode N. Like he never met it, even though he meets it in both versions of the film. But I suppose that has happened before. The rest of the movies are definitely canon though. M01 and M16 have direct connections to the main anime, and the other films are sometimes loosely mentioned. The events of M02 for example were mentioned during the Lugia Whirl Islands arc. And in one episode of DP, Dawn still had the Lunar Wing she bought in M10.
To be fair, Ash is pretty forgetful. In OS, he pokedexed every Pokemon, even after having met it once.
Truth to be told, Ash seemed to be even more forgetful in BW, where he dexed Pokémon he already had (Buizel and Corphish).
However, he does that for the audience’s sake, so that’s somewhat excusable.
I've seen the anime when I was a child when the Season 1 first aired, but just some bits and pieces. Also, I've seen the very first movie, Pikachu's vacation and Mewtwo Strikes Back. Since then, I haven't seen any of the succeeding episodes and titles. I've played the games until Black and White era. Now I want you guys' opinion if it's worth it to start over and watch everything from the beginning, including the movies in a chronological order or is it not worth the effort?