Whenever you randomize a Pokémon game, battle-wise, it can always become a completely different game, especially so with how much you decide to randomize in a playthrough. However, there are certain instances where what happens is just so wild you can't help but laugh. For example, in a recent randomized nuzlocke I've been doing in Platinum (in which I randomized what moves they will learn), I chose a Ludicolo as my starter and ended having this moveset: Basically a fire-bending Ludicolo. Yes, that was it's starting moveset. It was hilarious. Were there any other funny moments you've had in randomizing a Pokémon game?
In a Crystal nuzlocke I tried once, I was stuck in a battle with Silver, who had a Lapras that knew attract versus my Espeon that knew Lovely Kiss. All damage dealing moves, when they actually landed, hardly did any damage because of their randomized types. It must have gone on for nearly an hour. They were a cute couple, but in the end I guess my Espeon decided it just wasn't meant to be.
Randomized Sapphire locke. After getting a Gardevoir as my starter, my first encounter on Route 101 was a Lugia. The only move Lugia can learn from Levels 1-9 is Whirlwind. I was salty.
I was playing through a randomizer of white 2 and on the first route of the game, kyurem popped up in the grass. He kept annihilating me with dragon rage lol.