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I don't think I've ever chuckled from an Ash joke post-OS when rewatching the series up to DP a while back. The idiot kid just isn't funny, and his presence sanitized the show making everyone else less funny as well. The only thing keeping me watching as far as DP was the world being so happy and pure that it occasionally brought fourth tears. Which had to do with the world, not to do with Ash. He contributed practically nothing to the show when I rewatched it.
I didn't get far into DP before dropping it, but honestly the only thing I could think about Ash after a while was that show would have been better off if they just got rid of him. There is nothing "funny enjoyable" about him. Which would be fine if he had anything else going for him, but he's not cool like Gary or Alain, he's not wholesome yet talented like Richie, he's not a serious trainer like AJ, he's not a punk like Guzma, he's nothing. Ash is a nothing character. I would have honestly rather watched a sissy ass wimp learning to be a man like Wally than Ash, because at least then there'd be something there.