>>37589550Those memories you speak of come from the OS, which is when the writers had a lot more leeway with how Pokemon can be depicted compared to Johto onward, where the executives and TPC both started keeping watch on them to make sure they don't go too far off the rails, leading to a gradual homogenization into the usual formula we're stuck with today that they only recently broke with Gen 7 to play copycat with ANOTHER formula altogether, Yokai Watch.
If every season had its own truly unforgettable moments that weren't related to League Failures, like the episodes you mentioned, Ghost of Maiden's Peak and Island of Giant Pokemon, people wouldn't be so inclined to just ignore everything EXCEPT the League.
Not only that, Ash himself wasn't a complete block of wood compared to what he is now which is another result of homogenization, if you take away the meme faces, you still have the same Ash we've had for a long ass time.