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probably drifloon, its a whimsical pokemon with a dark side, and considering it can learn moves like constrict and wrap to act as nooses....
Errr, im sure someone already did this, but jackson jekyl?holt hyde from monster high.
I think Drakloak would be a good Pokémon, since it’s a ghost type, which kinda fits his shadow motif, and it can learn lock on, helping hand and baton pass, which are all good Pokémon moves for basketball.
Jackson Jekyl/Holt Hyde from monster high
Since he’s described as an ambulance chaser, I can’t help but feel like he would have an Audino, Unova’s Pokémon Center Pokémon. It’d also help him in legal work, since Audino have good hearing.
He probably would have a Pokémon that can prank well & can do well in a fight, or at least manage to avoid one. I’d say Grimmsnarl, since it’s fur can act as restraints and it has a decent attack.
A kid serving the tentacled horror Slenderman, I’d probably go with Malamar or Darmanitan, the latter because Ticci’s inability to feel pain reminds me of how darmanitan can turn into a statue at low health.
Italy from Hetalia
I think Grumpig might be a good Pokémon for either Haarlem or Haachama, since they’re warring personalities over the same body, & Grumpig is a Pokémon that can control bodies. It’s also you know, a pig, and can probably tolerate haachama’s odd cooking, and fits with their stitched pig emblem...
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
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.