Pokémon Gold and Silver

Best: The post-game
It’s been over 20 years since Pokémon Gold and Silver launched on the Game Boy Color, and its post-game is still something the series has yet to replicate. When you finish the initial adventure in Johto, the first games’ Kanto region opens up, giving you what is more or less a second game in the back half. As more regions have been made in each game, the idea of a Pokémon game that includes every region has been a pipe dream for fans everywhere, and that seed was planted by Gold and Silver. It was ambitious, and now that there are more than nine regions in the Pokémon series between the mainline and spin-off games, it seems unlikely we’ll ever see something like it again.
Worst: Chasing legendaries
With Entei, Suicune, and Raikou, Gold and Silver introduce one of the most frustrating Pokémon mechanics by requiring you to chase these legendary beasts all around the Johto region in order to catch them. This would be repeated in multiple games in the series with a few quality-of-life changes that made it easier, such as showing their location on the map or making it so they don’t immediately flee a battle once found, but Gold and Silver started a real annoying trend that took several generations to get to a tolerable point.