2 > 1 > 5 = 3 > 4
Always tough deciding between Gen 2 and 1, but 2 gets the edge because the games were just amazing, and some of my favorite Pokemon are from Gen 2. And I really really want a remake of Ruby/Sapphire. I get so nostalgic when I think about those games and all the cool features they had. Diving, SECRET BASES, that awesome volcano, the weather system, and some pretty cool Pokemon. Gen 3 games were by far the most exotic Pokemon games released.