1. Black / White
After Gen 4 allowed GameFreak to become familiar with the Nintendo DS, Gen V entered the scene and delivered a near flawless Pokemon experience. More new pokemon were introduced in these games than any other while no previous pokemon returned, and this was also the first generation to not have any references to previous regions, giving it a stronger sense of identity. So many areas of the game's overworld have unique and memorable visuals, and each area feels alive and full of life. Your rivals in addition to N also made for some of the most well written characters weve had in the series. and you can not deny that Black / White had the best story of any generation. It supposedly took them two years just to write the dialog script for these games, and it shows. but my overall favorite feature was the Entralink, and being able to send your character to your friend's game and interact with them. It was overlooked by many, and ironically is a feature a lot of people seem to beg for in the recent entries.
2. X / Y
These games felt more like a series reboot than anything else, and I was okay with that. These games just seemed to take a step back, bring a new dimension to the pokemon series, and focus on just making the game accessible to all players old and new. The introduction of the Fairy type and some changes to the type chart also brought a lot of much needed balance to the games. Mega evolution was fun until they decided to try and forget it existed. And not to mention it also brought the introduction of the Pokemon Timeline, and canonized that some games take place in a universe where Mega evolution never existed, while others do.
3. Sun / Moon
These games just took the entire Pokemon formula, threw out half of it, and did who-knows-what to fill in the gaps. We got the introduction of Ultra Beasts, being creatures that arent even pokemon but still behave as them. Z-Moves were introduced as a simplified form of Mega evolution, which i was not a fan of. This game also had a pretty good story to it, with the whole mystery of the Aether Foundation and the main villain team being nothing more than a group of thugs. There were also no gyms, and instead had island trials, which were a bit lackluster to me, but still an appreciated change of pace.
4. Diamond / Pearl
these games were so sloooooow. These are the only games to be limited to 30 fps while all the others run at a smooth 60, not to mention the animations take up about thrice the time as other entries. These games also had more HMs than any other games, and was the only one where I felt obligated to have an HM slave just to make progressing a bit easier. But one thing I really did like were the starter pokemon. Empoleon and Torterra both have some of the best designs to date and both have exclusive type combos. Infernape on the other hand did not, but it is still a cool design.
5. Gold / Silver
These games suffer fro ma serious case of bad pacing. Everything runs smooth up until you get your fourth badge, and then from the 5th onward its just rapid fire badge collecting until you have them all. I have heard the argument that a lot of main flaws of the game only exist today because they were designed for connecting with your friends, which was only prominent when the games were first released. Thats fine, but it still doesnt help me enjoy the game. I love that the entire Kanto region is also available after beating the Elite Four, making this the best post game content in any game. But a weak story on top of bad pacing, and reaching the initial end of game around level 45 just isnt my cup of tea.
6. Sapphire / Ruby
I just wasnt a fan of these, and thats no ones fault but my own. I just cant get into the region, or find any real sentimental value in the story of characters. It also doesnt help that with ORAS, the games were dumbed down and removed a lot of the personality of the games, meaning there will never really be a definite version of these games. But really thats all I have to say. By no means are these bad, but they simply did not resonate with me.
7. Red / Blue
There are so many features that just were not introduced in the first games that it almost makes them unplayable. sure, its enjoyable to see how different it was, and that Gen 1 music is some of the best, but these games simply did not age well.