By "most fun" I would actually say gen 6. Not because they're good, but because they were exciting and new and they didn't reveal their evolutions so we were speculating for the longest time how they would turn out. It's hilarious but also kind of typical how the girly furfag one turned out to be shit, the tough grass yolo kid turned out to be shit and the nerdy loser butler frog turned out to be a force of nature.
But my favourites are still gen 1.