6 - Generation IV. The first stages looked kiddie and forgettable, and the final stages were garishly decorated with spikes, stripes, and markings that didn't belong there. Oh, and a Fire/Fighting starter that didn't even come close to living up to the fantastic design of Blaziken.
5 - Generation V. Yawn. That's how I can best sum up the designs (as well as the usefulness) of the starters. A third Fire/Fighting starter emerges, and this one's the worst of the bunch. Even the garish Infernape was cooler than this loser. The water starter was... there..., and while Snivy was extremely cool and showed potential, its evolutions were only meh.
4 - Generation VI. This is a mixed bag for me. For the first time in a while, the starters all have interesting type combinations. Chesnaught is especially cool, and is a nice Grass/Fighting defender. Greninja is... okay, I guess, if not a bit overrated. The reason this is so low is that I really don't like Delphox. First off, it's odd to see a Pokemon that's 85% male wearing a dress. And then there's the weird head shape. Weird eyes, huge ears, just an odd design overall, and not really in a good way.
3 - Generation I. This is a meh generation to me. Yeah, they're decent, but honestly, neither of the three stands out to me that much. While I quite like Venusaur, I'm indifferent to Charizard and dislike Blastoise. This nudges out Generation VI because I prefer Venusaur to Chesnaught, I guess.
2 - Generation II. Yeah, the lack of secondary types is unfortunate. But the designs themselves are so damn good. Well, Typhlosion's and Feraligatr's, at least. Meganium's not my cup of tea. Bayleef's okay, though. But seriously, a badass alligator and a fire weasel.
1 - Generation III. In what other generation does every starter become a complete badass? I mean, Sceptile resembles both a king and an assassin, Blaziken's a fire eagle that kicks the crap out of opponents, and Swampert looks like some kind of mutant reptile. Plus, they are all at least decent fighters. This, to me, is the best of the best.