I'm sure we've all heard about Pokémon on some level. It'd be pretty hard to not have. However, hearing is one thing, and seeing is another thing, but maybe as you watch the internet explode with mad bouts of violence over these upcoming remakes (remember when "HOENN CONFIRMED!" was just a joke?), you're thinking you want to know what all the fuss is about yourself.
Maybe you've seen some of the anime. Maybe you've just seen internet videos parodying the series. But you've never played the games.
Well, if you're sitting down and thinking about starting the series, then maybe I can give you an answer. Or about seven hundred of them, at least until the next generation comes out.
So you think you want to play Pokémon. It's a huge series though, spanning nearly two decades now. Naturally, that means there's a whole lot of games, with all kinds of spinoffs and side games to boot, and you have no idea where to start!
First, we need to ask an important question: Do you want to play Pokemon because you want to play Pokemon, or just because you've never done it?
If the latter, look into the series in general until your answer becomes the former. If it never does, you probably shouldn't play Pokemon - I will never tell people to buy things they don't think they want/will enjoy. Money doesn't grow on trees, and Nintendo games in big franchises like this rarely drop to a price that makes them worth it if you end up not liking the game at all.
Okay! So you want to play Pokémon. To start, let's set aside all of the spinoff titles, like Mystery Dungeon and Conquest and focus on the main games.
Now, a lot of suggestions people usually give are based on having experience in the series already, though this isn't necessarily always the case - it may well be everything I'm about to say is completely off base with the opinions and experiences of others, but for the sake of sharing, I'll share it all the same.
For instance, I think HGSS is probably the worst set of Pokémon games (which does not make them bad games exactly), but it does provide a lot of nostalgia for the first games - and if nostalgia isn't your thing, if you won't think it's super awesome to go back to that one place you were at in another game a long time ago, then a good deal of that will be lost on you. HGSS also has other flaws to it, flaws I'll bring up further down, but for now let's just leave this as an example of the whole suggestions based on experience thing.
Personally, if you want to start the series fresh, with no experience at all, I would say you have a few options here - though you probably already know that.
If you think you might like the series and just want to try it, not worrying too much about things beyond basic aspects like collecting and battling, then I would grab X or Y to try it out. It's got all the updated mechanics and features, plus you'll be able to experience all the current online stuff (whereas going into any older game cuts you out of that). X and Y is really good for this because it's quite a bit easier than many previous games, makes breeding and battling competitively online more accessible than ever before, and it has a ton of Pokemon in it... though that could be overwhelming! X/Y's Pokedex uses 400+ Pokémon altogether, and that's not including the Pokémon you can get through other means in the game, though that's for another time.
Another option is the remakes of the first games. Very, very solid games that still hold up, but they're missing a lot of the mechanics that have been added since (being over ten years old and all). You might get a very enjoyable game there and really have a lot of fun, but then if you jumped into a current game afterwards, you could, again, get overwhelmed. That shouldn't stop you if you want to see where this all began, however, but do keep in mind a lot has changed since then, and those remakes went for accuracy in a lot of places, meaning certain features even from games up to that point weren't included.
Next, there's Black and White, which I personally find to be the best games in the series - which could be a bad thing for newcomers, because if you end up agreeing, you'll be biased against everything else forever if it doesn't hold up. Now, B/W has very up to date mechanics (only a couple of years old, being of the most recent generation before X/Y), a great story and cast of characters by Pokémon's standards (comparatively, X/Y's isn't even there for most of the game), and only uses the new Pokemon it introduced until the post-game - for old players, this was either great (I'm in this camp - I want the new games to be all about new things like this) or terrible (others don't like venturing outside their comfort zones and using Pokémon they aren't comfortable with, which is understandable enough). It's also pretty challenging, like the original games, and it and their sequels have a hefty amount of post-game content, which will make up for the lack of online. However, the designs can be hit or miss with fans (I love them) - as a newcomer, this may not be an issue with you, but you probably won't recognize most of them since marketing of the series tends to be of the ones they can bank nostalgia on, so keep that in mind. However, there is one thing to consider with these games: These games are good, and another thing you could think about doing is saving them, BECAUSE they're good. Save them for if/when you feel "done" with the series. Many fans were brought back to the franchise with these games. They give a new and "fresh" feeling that games that rely on older Pokémon and older regions don't have. Of course, this will partially be lost if you play games that came after it anyway, but it's something to keep in mind.
Then, of course, your last option is waiting for the upcoming Ruby and Sapphire remakes - I can't comment too much on them since they're not out yet, but I can say that these games (the original versions anyway) are pretty great, and it looks like they'll be adding a ton of new features for online (so if you don't like some parts you can at least entertain yourself with that) and offline, plus you'll be able to talk about it with everyone else once it comes out (socializing is always fun), whereas you've missed the boat for the most part with X and Y. They'll also, of course, be the most current games, so any of the advantages getting X/Y had will also apply here, with the added bonus of the game not being super easy (like X/Y) if it's an accurate enough remake, and if it adds in elements of their followup game (Emerald), there's going to be a lot of post-game content to look forward to as well.
Of course, with the good, there is the bad. There aren't many I would say to flat out avoid, but there are some.
As I mentioned earlier, a popular choice is Heart Gold/Soul Silver. Ignoring the whole "nostalgia" thing I mentioned earlier, these two games (and the original versions) are unique in that you can travel to two regions (a new one and then the original from Red and Blue) and fight two sets of gym leaders - on the tin, that sounds like it would therefore be a bigger and better game. However, this is just simply not the case. Because this game was made to be playable on an original Gameboy (and because the remakes prioritized being accurate over fixing the game's flaws), the new region is really, really small. This wouldn't be so bad if there was a lot to do in the second region in the game (the one from the first), but this isn't the case either. While the remake stuffed in some legendary Pokémon to go after, ultimately, the "big" region is devoid of much of anything to do at all. You dash to a few towns and fight the gym leaders in them - and with how the levels are scaled to account for there being two regions, despite the maximum level having not changed, your journey through these 16 gyms will still ultimately not be too far from a journey through 8 in another game, and I would argue the first game is much more satisfying as that bigger region is filled with adventure and challenge and things to do in that version. The Pokémon distribution is also rather messed up, among other things, but in my opinion, considering the staggering amount of flaws this game has, I have a hard time telling people who like the series to go for this game, so I just can't in good conscience tell people who have no experience at all to go for it - except perhaps if I instill the knowledge into them that it'll be only up from there if they choose to continue.
Moving on, the original Diamond and Pearl had a lot of flaws, such as only one Fire type Pokémon outside of the starter and a lot of lag in battles, that Platinum later made up for. Now Platinum is considered one of the best in the series, so while that might be another place to start, it got really annoying with HMs (so-so moves you put on Pokemon to use effects in the overworld, such as moving rocks or traveling across water), which can be off putting, so I would hold on that one too for now. Also, obviously, don't go for the original Ruby, Sapphire, or Emerald since you'll have updated versions of them in a few months for... about the same price, given Nintendo game prices and all.
All in all though, it's a huge series with a huge fanbase, and there may well be someone out there who disagrees with everything I've said here. The easiest thing might be to just ignore everything you've just read, and instead go look at which Pokemon are available in which games. From there, pick the one that has the most ones that you think you'd like, and get that.
If this helps you, I'm glad! If this confuses you, then I wouldn't be surprised. Sorry about that! If you vehemently disagree, as I said, it's quite possible. Regardless, I do hope someone out there could get some use out of this, and if that happens, then that's good enough for me. Take care everybody!