Because believe it or not but I have never played one I hear all this good stuff about pokemon games and I want to experience it myself.
It depends on how familiar you are with the anime (if at all) and what system you have. If you want to experience the same world as the anime (Ash, Misty and Grey) then I'd recommend Yellow (for the fact that you can interact with your pikachu) or Red/Green. If you're not concerned about that, then Gold/Silver on GBA is one of the best in the series (now remade as HeartGold and SoulSilver). However, if you want to try out the new generation, then maybe get Pokemon X or Y on the 3DS.
Most of the games have contained storylines (Black/White and Black/White 2 aside) so you can really play them in any order. Since you won't have the nostalgia factor, I would honestly go for one of the newer titles. Gameplay, graphics, post game content, online content... its all so much better with the new gen stuff. (Especially since the first games were on GBC!) Pokemon X or Y, or Pokemon Alpha Ruby or Omega Sapphire, all for 3DS, would be your best bet!
All Pokemon games are fundamentally the same. New features have been added as the franchise has aged, but the basics are still the same. I'd recommend you just look at what game appeals to you the most and go with that. When in doubt, just pick up the most recent game (Currently this is Omega Ruby and Alpha Sapphire.) That said, I did really enjoy FireRed, Emerald, and Gold/HeartGold with HeartGold being my personal favorite. I'm not a huge fan of the newer generation of Pokemon games. Especially Black/White and X/Y.
I started a long time ago with Pokemon Blue, but if you are just getting into it at this time, I suggest Ruby and Sapphire for the GBA since it should be really easy to find. Or if you have a DS, I would get Platinum. You get to have a fancy villa and buy expensive stuff to show off to friends that visit you~
Honestly, I started playing Pokemon with Red. It may seem like a really old game, but it's honestly the best way to get into it and become familiar with the game. Plus, whenever you talk with someone about the Pokemon games, the first ones will always pop up in discussions so you'd want to have some background knowledge on the game. The best part is that they don't have as much Pokemon or any other additional features so you get to play a somewhat, simple game with just the story line. This is useful if you want to get used to the game mechanics.
I don't think it matters which version you start with. You can pickup any version that looks cool to you and try it out. That's what I would do anyway if I never played Pokemon before. Most of the games contain different story lines so you won't be missing out on much if you start with the most recent versions. However, despite what I said earlier, I'd recommend the older versions to familiarize the controls and since the older versions are less complex than the newer ones (more items, more pokemons, more weird effects, etc..), it is better to familiarize with all this before learning some of the new stuff.
Each Pokemon game have their own storyline and you don't need to start somewhere specifically to know the game. Any one you start with is fine although some games have different features like beauty contest. If you want to see how Pokemon have changed over the years, start with the older games and work your way through the different series
Thats hard. I grew up with pokemon, and so I just started from the beginning. If you are familiar with the anime, then just start with whichever season you are familiar with. It also depends on what type of system you have. All pokemon games are pretty much the same though, and I think that although they are enjoyable, a lot of that enjoyment comes from nostalgia.
You should buy one of the newer DS handhelds and wait for the re-release of Pokemon Blue, Red and Yellow on the new devices! That way you can experience everything right from the beginning. On the other hand, you won't have running shoes, so maybe start with the first generation remakes; FireRed and LeafGreen.
I'd recommend starting with Pokemon Emerald (or, with the newer handholds, maybe Alpha Sapphire). It wasn't the first game I played, but it's still my favourite after all these years. While keeping the classic look, it has so many additional features and the landscape is beautiful! This is making me nostalgic; it has some of the best music, in my opinion, as well as actual Pokemon.
