The Pokémon world is an enormous one, one that spans over 20 core titles (mostly with slight variations) and countless other side stories (30 by my count), but for newcomers into the series, it seems like an overwhelming lot to comprehend. So let's say you're a new player to the series, or an old hand looking to restart on the road to the Pokémon League—allow me to rank the series so you can catch 'em all the best.P
Before I start, I have to point out that this list isn't Kotaku's picks, no—they're mine and mine alone. One extra tidbit: this list does not mean that any one game in the series is worse than the other; if I could, I'd give each game a gold star. I mean I did play them all... all.
P
This post will only talk about the core series of the Pokémon games, spanning from the originalRed and Blue to the current Black 2 and White 2. For the sake of time and arguments I've chosen to eschew myself headaches by omitting the many many spin offs and side stories in thePokémon Universe.P
This list is by no means definitive; in fact I look forward to hearing from you, our readers, about your own rankings of the Pokémon franchise. Maybe you can change my mind in the comments below!P

1. Pokémon Generation IIP

Gold/Silver/CrystalP

P
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Nothing will take away just how special the first generation of Pokémon was, but Generation II was where Pokémon really started to open up. The formal introduction of dual-types (Charizard can now fly! (I know he could in Yellow, but he couldn't inGreen/Red/Blue)), and the implementation of a day and night cycle created different ways to play. For the first time, the time of day mattered—certain Pokémon could only be caught at certain times, for example. This made gameplay more frustrating and more interesting. On top of having day and week cycles, Generation II expanded on the Friendship/Happiness system that was introduced in Yellow, making Pokémon grow via their "devotion" to their trainers.P
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But new elements aside, Generation II had (imo) the longest main game section with the addition of the original Gyms. Bringing back Brock and allowing the player to fight Red was just a dynamite concept of fan service, and giving Red a Pikachu was definitely a great shout out to the Anime/Manga fans. Plus the cell phone system allowed trainers to be battled again, resulting in more replay value.P
On a personal note, 251 Pokémon was just the right amount!P
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Pokémon Crystal, being the extension ofGold and Silver, is perhaps the best Generation 2 game. Adding for the first time the choice of gender for the main character, an additional Suicune centric plot, and the battle tower, Crystal adds more replay value to an already packed installment.P
Don't worry if you can't find a Gameboy to play Generation II; they remade Gold andSilver into HeartGold and SoulSilver in Generation IV for the DS.P

2. Pokémon Generation IP

Red/Blue/YellowP

P
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The games that created a worldwide phenomenon still hold up pretty well today. Capturing all 151 original Pokémon is still a challenge today. Even without the addition of running, and the weird implementation of "dual types", there is always something to love about starting out in Pallet Town, taking down Team Rocket and then beating the snot out of Blue (or Gary). The most gratifying part of playing Generation I is knowing that it directly connects to Generation II.P
The hard part now is finding a Gameboy or a Gameboy Advance (Red/Green were remade in Generation III) to play these games.P
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Yellow is the definitive Pokémon game experience for any Post 90's generation child that grew up watching the Pokémoncartoon. This game was made to closely resemble the Pokémon TV series with the addition of Team Rocket. Most importantly, this game had a Pikachu that would follow the player around. This Pikachu, a mirror of Ash Ketchum's (Red's) Pikachu also said "Pika Pika", which was unlike the regular garbled sounds that supposedly made up Pokémon noises.P
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Yellow also included a fun little mini game that involved a surfing Pikachu.P

3. Pokémon Generation IIIP

Ruby/ Sapphire/ Emerald
Leaf Green/Fire RedP

P
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With the addition of running, better animations, contests, and double battles, Generation III deserves a higher place on this list, but the new focus on the IV and EV value systems, in my opinion, really made the games a little too serious—dropping them down the list to number three. Also,Pokémon contests weren't exactly my cuppa tea, but I can see the appeal they have.P
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The biggest and only issue I had with Generation III is the fact that the Pokémon designs seemed to get weaker—I mean just look at Torchic and its evolution Blaziken(also look at Feebas)! There were also some odd design choices, such as getting rid of the time cycle and focusing more on the weather element.P
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There really isn't a break out title in Generation III, but if I had to pick one, it would be Emerald. Like Yellow, Crystal, andPlatinum, Emerald is an extension to Rubyand Sapphire.P

4. Pokémon Generation IVP

Diamond/Platinum/Pearl
HeartGold/SoulSilverP

P
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The first fully 3D Pokémon games were also the first ones in which Pokémon could be traded and battled with over the internet, without having to use a dinky link cable. So why isn't Generation IV ranked higher even though it contains the remakes of Gold and Silver? Because fundamentally, HeartGold and SoulSilver are remakes (even if I could have my Typhlosion follow me around).P
Generation IV exists as a milestone and a technological stepping stone in the Pokémonuniverse, however as a standalone game it doesn't change the formula in place since Generation II, and it doesn't add much more than what was already added in Generation III. It does however get points for making Pokémon better looking and paving the way for the newer animations that may be found in the upcoming X and Y.P
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HeartGold or SoulSilver, you can't go wrong with either. The extra gym battles and the nostalgia make these remakes a bit more entertaining than the three main games of Gen IV.P

5. Pokémon Generation VP

Black/White
Black2/White 2P

P
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The first time that a Pokémon game has received a direct sequel, the Generation V games in my opinion didn't do much more than just increasing the (already quite large) number of Pokémon. There are now, in fact, 649 Pokémon (excluding the ones seen so far in X and Y). The only thing I liked about Generation V that wasn't found in the previous games was the fact that Technical Machines became very similar to HMs, in that they have infinite uses. This addition was, in my opinion, a double edged sword, making the game easier while taking away from the challenge. I still can't decide if having flamethrower as a TM is a good or a bad thing yet. P
Black 2 and White 2 were my favorites during this generation cycle. The storyline was more accessible for players if they had previously played White and Black, but the games were able to hold their own as individual titles. The additions of the White Tree Hollow and the Black Tower provided hours and hours of extra Pokémon battling with an added "story" extension. These games were fun and engaging, but after playing so many Pokémon games, at the end of the day, Pokémon fatigue sets in. There are just too many to capture and trade in the fifth generation.