I don't care if he's 30 by time they take place, it must happen. And he needs to be an even bigger asshole, too. Everytime his theme starts playing the player should recoil in fear because they know that his level 100 Blastoise is about to rape you.
At the end of a cave? Your Pokémon all poisoned with no HP left. Gary appears.
Leaving Team Whatever's HG on the way to the Pokémon center? Gary appears.
Gary should appear in the middle of the credits. Gary should appear while you're healing your Pokémon. Gary should challenge you before you even get your damn Pokémon.
The last sound you hear before you die?
His theme.
Godbless you Gary, a real Pokemon master.
