7. Gary Oak (Pokémon Blue)
When you look into the whole Pokémon story, it's a lot darker than it seems on the surface. There are a lot of theories out there - the main one being that Ash is merely dreaming the entire thing or that there was a war in Kanto that killed off most of the adults. When I first picked up Blue as a child I didn't see any of this, I just wanted to collect and battle Pokémon and at the time Gary Oak was nothing more than an annoying rival who ruined my chances of completing the Pokémon League many a time. When I look back at it now, though, I realise that Gary Oak's story is a pretty sad one and I fully understand his attitude towards everyone. One of the theories out there is about why Gary Oak acts the way he does towards you, always popping up at those crucial moments. Every time you battle Gary, he brings out his Rattata/Raticate until the battle on the SS Anne. After defeating him on the ocean liner you don't see him again until Lavender Town, which is the final resting place of Pokémon. When you battle him again, his staple Pokémon is nowhere to be seen and it seems his sudden motivation to beat the elite four. When he finally manages to defeat the elite four, the player turns up and crushes him (after a few tries anyway), making his victory short-lived. Gary Oak may have been annoying, yet he lost his favourite Pokémon, his grandfather prefers you over him, you snatched victory in the Pokémon league away from him and his parents are dead. Turns out Pokémon wasn't exactly the happy game it claims to be when you mix this theory with a few others out there.