I liked Heart Gold/Soul Silver the most. The gameplay is a bit slow IMO, but the actual amount content is incredible. If you don't get bored of the gameplay you can spend 100+ hours on this one.

I liked X and Y as well...and I think a lot of the gameplay issues I had with the older games have been resolved in those titles.

I've noticed you enjoy retro games...so if you want to enjoy Pokemon in its original form...waiting for Red/Blue/Yellow on the 3DS might be worthwhile. I just believe those games to be very dated now...as others have said. I think Heart Gold/Soul Silver will be your best choice for that reason anyway...since they're actually remakes of the 2nd generation games, which themselves made tons of improvements over the 1st generation.

Why play Pokemon when there's the vastly improved, mature, Digimon Story Cyber Sleuth? You missed Pokemon when it came out back then? Well, Cyber Sleuth was made to cater to the older fans when Digimon started back then with a mature Digimon game, and actually delivers on the word "mature," unlike Pokemon(specifically, Black/White).

I recommend starting in order of release....or just start with X/Y.

I've been there from the start, and it's the truth: the orginal games didn't age so great.

Between the endless battles that happened if you made the mistake of clicking "Rage" against a ghost type,  the skipped moves if you over leveled a Poke, to the extreme balance issues against the Psychic type, Gen I had loads of issues that make it borderline unplayable now, especially when compared to the newer games in the series. 

Thankfully, it was all fixed in pkmn Gold and Silver, and I think that's by a mile one of the best ones in the series and layed the template for what many newer fans still like about the series today.

And it's not like this is the only series that suffers from aging poorly btw. Try playing GTAIII vs even any game in the series. You'll almost wonder how anyone even played through that game in 2001.

I think those that don't hold the originals as the best pokemon games in the franchise were too young to ever experience it. They were probably exposed to the later generations first.

The originals are by far the best and the most charming. Gold & Silver are amazing as well basically an upgraded version of the originals plus 100 more pokemon. Ruby & Sapphire were good as well. Then the franchise began to get a bit stale.

X & Y definitely pumped some much needed life into the franchise. Such a great instalment in the series.

But yeah playing the originals (Red/Blue/Yellow) and watching the anime...what a time to be a kid back in the day!

How is this a debate...? o: They're from the same gens. Crystal is even just Gold/SIlver, but... more. I get debating between gens, but games within the same gen? Wat..? : I

Yeah, I figure it's got more extras added on, as well as being able to play as a girl. I'm fine with any of the 3 games, as gen 2 was my fav among the pokemon games xD

I would go Yellow and then Gold. That's how I did it back in my day. Also, because yellow has Pikachu!

Indeed. Gen 2 was def the best ; )

Yeeah, Gen 2 just had so many great things about it. I feel pokemon games after gen 2 haven't reached the greatness it had. : ( I hope some day a pokemon game lets you go to different regions like Kanto, Johto, Hoenn, all of them if ever possible...

Best made in the series is HeartGold/SoulSilver. Recent ones worth giving a try are X/Y and ORAS.

Old ones to try are Crystal, FR/LG, and Emerald.

You can try R/B if you want, but if you have no nostalgia for them then by todays standards they're VERY rough games. If you're going to play an old school Pokemon game go for Gen 2 games. Much better polished and overall better quality than the originals