Hi everyone. Let me start off by saying that, for starters, I'm old (36). This means that when the first Pokemon craze hit the US, I was roughly 19 years of age. This meant that I would completely miss out because, you know, image, girls... you get the picture. Since I didn't get "hooked" like alot of you early and mid 20 somethings, I never had any interest in playing the franchise. When the second generation was released, I was playing my Dreamcast. When the third generation hit, I was too busy killing hookers in GTA. When the fourth generation hit, I was already completely tuned out of handhelds altogether. It wasn't until literally like, a week ago, that I started to get interest in trying the franchise out. I decided to go on Ebay, and procure an original Gameboy due to having one as a kid, along with a few stellar classics. After that, I did some research on the top games for the system and discovered that the original Pokemon games (Red and Blue) where held in really high regard. So I decided, what the hell. Better late than never... right?

So, I'm 100% going to get Red or Blue, because I have always been adamant on starting from the begining when attempting to play a franchise for the first time. But, I am fully aware that just as with most IP, evolutions DO happen, and usually for the better so, I was just wondering what some of you vets think about someone doing that (starting from the very beginning and working their way forward through time). Do you think it's a good idea? Or should I start with a newer version? Like I said, I am getting Red or Blue, or both no matter what. I just don't know if I should start with those titles as an introduction or if it would be better to come back to them after playing the newer versions. 

You have a 3ds?
Play X and Y it's amazing it brought me back into the series after not caring since 2003

In this case, I'd probably start with the newer titles.

Red and Blue were phenomenal for their time, but they haven't exactly aged well. Although I've heard mixed reactions from completely new players to X&Y also.

So if you don't mind the noticeably dated graphics, then R&B is the best place to start, or Yellow if you can get your hands on it.

Pokemon Blue was good. My favourite is "Gold" - Even today it's somehow more fun than the new Pokemon.
In my opinion, Digimon Story Cyber Sleuth is better then the last Pokemon-Games. It has a awesome jrpg-story with Shin Megami Tensei-Stil, 240 playable Monster and great characters. i have pokemon Blue, Gold and X-edition, the story is so boring -.- So I wish new modern Pokemon-games like Digimon Story. For your question: maybe blue or red, yes : )

Play the originals (Red/Blue/Yellow), play Gen 2 (Gold & Silver) Best games in the franchise.

Then jump to X & Y.

Won't be disappointed.

Also if you hate the small screen I would recommend emulating the originals on a phone or computer. The game runs 100% accurately so no worries about emulation giving a different experience, at least no more than not being a kid experiencing the novelty of trading and battling over a link cable. There are some nostalgic factors which cant be experienced today with our technology, expectations, and age. Nevertheless the games are stills pretty amazing. Starting from the beginning is a good idea because it will allow you to appreciate some of the evolutions(pun intended) the series has made.

I'd go FireRed or LeafGreen > HeartGold or SoulSilver > OmegaRuby AlphaSapphire > Platinum > Black or White > Black 2 or White 2 > X/Y just to be able to get a feel for all 6 generations.

Hmm, for first game to dive in, maybe you should try the remade version of Red/Blue. While Red/Blue was great for its time, it hasn't aged well. Without the running shoes, walking through that game is painfully slow. Silver/Gold is better in my opinion, so if you can get the DS remake, try that too. Otherwise, you can try Pokemon X/Y or Omega Ruby/Alpha Sapphire. Those 2 are on the 3DS and are the most up to date, so that may be better for you.

Also forgot that if you have a 3DS, you can actually get Red/Blue on the VC soon. So that could make it easier for you to play the first pokemon.

I'd say that FireRed and LeafGreen are better games to start off with, as Red and Blue haven't exactly aged well, but they far from hard games, and the originals are still decent starting points IMO.

I know, I've been there xDDDD. I feel very stupid right now, because I missed some great games just because of coolness. It took me a while to admit that I'm not cool and not designed for the popularity, and I prefer to play Pokémon at home than go out on dates and parties XDDDDDD.

OT, I think you can start with the new ones (X or Y), since you have Pokémon from each gen, and then, if you're interested in a particular gen, move to those games.