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Gen 1 is good because it started it all and its fun to play for nostalgia. Gen 2 is good because it takes what Gen 1 made and expanded on it. New types, adding gender, the Special stat split, etc. Gen 3 is good because it has really catchy music and brought in the interesting dynamic of two teams, one of which is the "villain" team, depending on which version you play. Gen 4 is good (yes I'm serious) because it brought us the divide of physical and special moves that aren't dependent on type, not to mention Lucario. Gen 5 is good because like Gen 3, it has great music. In addition, the storyline became more sophisticated and connected players from around the world with the Global Link. The moving battle sprites are also a welcome change. Gen 6 is going to be amazing with the completely 3D world and battling. Pokemon Amie looks great; can't wait to spoil my team rotten. Customizable trainers have finally gone mainstream, which is probably my favorite part thus far.
4e is not D&D, but WoW making a Disguise check. Pokemon Black Friend Code: 0605-2800-9952; Trainer Name: Solace; First Pokemon (roleplaying): Snivy (Monty)