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WARNING: This answer may reveal plotline(s) of some seasons, old and new. Read at your own risk.

The Pokemon Movies are NOT canon (meaning they do not follow the storyline or flow of the series). However, some contain references to seasons, and should be viewed at certain ideal points in the series in order to maintain a sense of continuity.

This broad question will be gradually answered as I watch each Pokémon movie. There have been 11 Pokemon movies made to date - seemingly 1 movie for each season in the series.

Pokémon: The First Movie:

This movie revolves around Mewtwo and shows some similar footage to that of parts in episode 63 - "The Battle of the Badge", as well as episode 67* - "Showdown at the Po-ké Corrall", which feature appearances of Mewtwo. It is recommended to watch these two episodes, both found in season 1, before watching Pokémon - The First Movie. Pokémon: The Movie 2000: This revolves around the Orange Islands. Ash and Misty are travelling with Tracey, who has a Scyther, and Ash's Charizard has a bad attitude. This movie should be watched in Season 2 sometime after episode 99* - "Tracey gets Bugged", where Tracey captures a Scyther and before episode 107* - "Charizard Chills", where Ash restores Charizard's loyalty. Pokémon: Spell of the Unown: In this movie, Ash has a Totodile and Brock only has a Zubat. In the accompanying Pikachu short, Misty has a Poliwhirl. This movie should be seen sometime after episode 153* - "The Totodile Duel" in season 3, where Ash attains a Totodile and Misty's Poliwag evolves into Poliwhirl, but before episode 167* - "Hassle in the Castle" in season 4, where Brock's Zubat evolves into Golbat. Pokémon 4Ever: Celebi - The Voice of the Forest: In this movie, Ash has a Bayleaf and Brock has a Crobat. This movie should be seen sometime after episode 201* - "Current Events", where Ash's Chikorita evolves into Bayleef and Brock's Golbat has evolved into Crobat (from episode 198* - Control Freak). Pokémon: Heroes: In this one, Misty is still travelling with Ash and has a Politoed. This movie should be watched sometime after Episode 249* - "Outrageous Fortunes", where Misty's Politoed evolves, but before episode 275*, "Gotta Catch Ya Later!", where Ash, Misty and Brock split.

* Episode numbers from some sources may be 2 episodes off, compared to episode numbers here and at http://bulbapedia.bulbagarden.net/wiki/, due to two episodes ("Holiday Hi-Jynx" and "Snow Way Out") being aired considerably later than originally intended. See http://bulbapedia.bulbagarden.net/wiki/Holiday_Hi-Jynx.

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Q: At what point in the Pokemon series should you watch each Pokemon movie?
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