What would you say are the Pokémon that best exemplify the five Contest categories?
Well, beauty has to be Milotic, right? ‘cause originally Milotic’s very evolution was tied to the beauty stat, and no other Pokémon has that kind of connection.
I reckon cleverness and toughness are probably Alakazam and Machamp respectively, since in the original games they sort of form an opposed pair of brain and brawn.
Coolness is hard because it’s something that you know when you see it but is hard to define; if you look at the moves associated with it, they tend to be either flashy, dynamic and powerful or quick and accurate, so there are kind of two aesthetics blended in there. I think I can probably appeal to popular authority, though, and say without fear of contradiction that the coolest Pokémon of all time is Charizard.
Cuteness is downright impossible because there are so many Pokémon you quite justifiably could pick. Also I happen to think Dunsparce is the cutest Pokémon ever but I suspect this is a minority view on my part. I might have picked Pikachu for this because of his universal popularity, but Cosplay Pikachu firmly establishes him as being linked with all five categories. The best I think I can do is narrow it down to two – Eevee or Togepi – because I think the concept of ‘cuteness’ implies the potential for growth, and those are both Pokémon for whom that’s a really important design element.