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Without a doubt Charizard. Not only was it the first one, but Charizard disobeying Ash had the more serious consequences - he lost in the Pokémon League because of it. Dawn and Iris? Nothing that serious. Also, it was only when Ash saved Charizard's life that the lizard decided to finally obey Ash; and before then, it had random moments where it wanted to battle by itself (Like VS Blaine's Magmar).
It's hard to rank either Mamoswine or Excadrill above the other, because quite frankly, they both sucked. Mamoswine's just seemed way too rushed, and Excadrill's was pretty much forgotten about until the Georgia episode.
How was Mamoswine rushed? They even had it cost Dawn a contest.
Swinub-Pilowine-Mamoswine didn't take that long at all. There was only 20 episodes of it as a Swinub (and it hardly appeared during those 20), and only 3 episodes as a Piloswine. Ash's Charmander obeyed Ash for 32 episodes before it evolved into Charmeleon; and during those 32 episodes, unlike Swinub, it was used quite a bit. So we actually saw Ash bonding with Charmander, then BAM, it evolves.How was Mamoswine rushed? They even had it cost Dawn a contest.
Why would they need to advertise an old Pokemon like Swinub? It was clearly just there for a while to show it obeyed Dawn. The Mamoswine story itself was handled fine, the ONLY problem is Mamoswine never got a full battle to itself afterward. It was always in double battles.
Charizard was handled the best, but Mamoswine certainly wasn't handled badly.