Firstly, Im not talking about his team, Im talking about what he switches in.

I started watching some of it, and Ive almost finished the orange league series. I noticed that ash sometimes sent out a smart choice, like pikachu against something water or flying, but sometimes he sends out the most random pokemon, in total disregard to what his opponent is using. I've seen him go completely against the whole super effectiveness thing, and just use something like Charizard against dragonite. You know, that sort of thing. The best part is when he wins by it. Does anyone know how he actually picks what he'll use?

In the anime, the type doesn't make as much of a difference as the trainer.
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I guess he just likes to use his Pokémon equally. Y'know, the "love and nurture" crap, as opposed to the "You're weak! Get outta here!"
crap.

You're only watching some of the earliest episodes...keep watching through the later ones when he starts to know what he's doing!

I do notice that often, if an opponent sends out a Pokémon he has (or another form), he'll try to match it. Common themes include one of the two evolving or learning a powerful move during battle.

I guess he tries to make the show more epic (without knowing he's on one).

Actually the show is half as epic as it used to be. The characters act TOO noobish; even Ash, who is a 'Pokemon Master'.

I think we all agree when we say the show isn't any good anymore.

Meh. I think that the anime is OK now. It was REALLY good up until the voice actor change, in my opinion. Just an opinion, though.

I only really see it when I'm channel hopping in search for something to watch. I never know when it's actually on, ever since Disney took over Jetix.

On-topic: The last case of Ash being stupid was when he was in a Bulbasaur vs Bulbasaur match, with a gym leader. He had some much better matchups with him.

I still watch the anime every week (on youtube)

I'm almost through season five, Ash just got a Phanpy.

EDIT: I just got to episode 238, Rage Of Innocence.(Best one yet in my opinion!)I take it that EP238 is the origin of RageOfInnocence's username...

Is that the one where red gyrados goes on a rampage. If yes thats one of my fav. episodes.