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What Pokémon would the characters have?

All three forms of Lycanroc.

Kakashi Hatake.
The way he’s described as on Wikipedia (laid back, apathetic, teacher,) makes him sound a bit like nanu. So a dark type cat. I think I’ll go with purrloin both because of theft/ninja and their shared half open eyes. It’s shiny coloration looks like him mask as well.

Naruto
 
Mind if I post a character instead?
Hercules (your choice as to which version of the character, doesn't matter if it's the Disney version, the version of him depicted in Smite, or something different)

No it's all right, thank you. I think Gallade combines very well with him.

Sakura Haruno.
 
Oh my favorite character! (unpopular I know) Anyway I'd say it's a tie between Medicham and Blissey, for the obvious fighting type and one being a healer, but also because both have pink on them and it's fits her theme pretty well.

Well that happened, uh Grimmsnarl I guess?

Atsushi Nakajima (Bungou Stray Dogs)
 
Man, the rest of the Kung Fu Panda series has been rotting on my bucket list for a while; I've only watched the first movie.
How about Togekiss? One with a ParaFlinch moveset, at that to reflect the disabling tactics?

Tsukasa Yugi (Toilet-Bound Hanako-kun)
 
Ribombee

Samus Aran
Only know her from smash, but considering she’s in space which doesn’t have oxygen, and battles a dragon regularly, she needs a ghost type that has super effective attacks against dragons. She also was good friends with pikachu in smash. So I’d go with mimikyu.
Steve? From Minecraft
 
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