I personally have soft spots for Gens 2 and 3, as they helped me understand gaming and the franchise in general, but as far as genuine greatness goes, Gen 5 is the best for me. It really tried to break the mold for Pokemon games in general and do new things with it that previous games just didn't do. Plus, it introduced me to a lot of what would become my favorite Pokemon ever, so I guess I'm kinda biased.
Gen V is my faaaavorite, omg. The region, the characters, the story, the music, the Pokemon, everything about it. I've loved every generation thus far, but I'm especially fond of Gen V. I love it so much.
Gen V, no question. I love the story, I love the design of Hilda, and most of all, I love the Pokémon. Unova gave me Golett, Golurk, Pawniard, Bisharp, and Sawk. I fell in love with Ghost types, Dark types and Fighting types due to this Generation.
My favourite generation... that's always a hard question, because Gen III, IV and V are pretty much tied, for me. I love all 3 of them...
Gen III has the most wonderful, vibrant graphics, and introduced 2 of my 4 all time favourite Pokémon (Metagross and Salamence), Abilities, the Battle Frontier (best feature of all time), Secret Bases, Contests, the Hoenn region... and started the whole remake trend.
Gen IV was the most balanced generation, and pretty much perfected most of the things Gen III did right. It introduced the physical/special split. And it's the generation that finally made justice to Johto with HGSS.
Gen V is cool in its own way. I value it because it is the only Generation set outside of Japan that I like. It gave us the PWT, Funfest Missions, and a more mature lore and Villain Team, which felt fresh.
But, if I had to pick just one... it would be.... Hmmm... If I picked with my heart, I would pick Gen III. But if I had to pick with my brain, I think I would have to pick Gen IV. It is the most complete and balanced generation.
Gen V is on a lone height here. Excellent story, nice music, good characters and really good Pokémon. I also actually like that, for once, it wasn't nostalgia pandering by putting older Pokémon into the storyline part of the game.
They also have excellent character designs and their sequels actually aren't just rehashes of the previous pair but with some small changes added to them.
I also solemnly believe as to why Gen VI and Gen VII suck as hard as they do is because Gen V set the bar extremely high and those other two have never come close to even a quarter of Gen V's quality.
Through the years I've found Gen V and II to stick out the most. In the end, I sat aside nostalgia and give it to Gen V. Although Gen II was legitimately great in its time and I enjoyed it so much. Gen V just hit it out of the park for me by making me use new Pokemon. I had settled on the same Pokemon over the years, and needing to look for new Pokemon made it a very refreshing experience. Plus, Gen V has a number of my top favorite Pokemon designs.
Special mention to Gen VI, mainly for having the best OST and the best region so far. Also Fletchling. Fletchling is so cute.
the most developed region, the most dynamic overworld both in visual and audio, death to third versions, pretty good story, great gym puzzles, based funfest missions and pokestudios (and musicals! i <3 them too). the pokemon all have such character and fit into the region so nicely and often take advantage of the moving sprites in creative ways. i can elaborate on any of these at length but that's basically what ive spent my internet career doing already
it also gave us the scraggy line. come on man you can't beat that
Definitely Gen IV. With the Sinnoh games, we got a huge, very diverse region, a great story, some of my favourite Pokémon and my favourite starters, amazing music... as someone already said, it was all very balanced and those games perfected what the previous generation already did right. With HG/SS, we also got the best remakes so far (and perhaps even the best games overall), plus some amazing spin-off games were released in Gen IV. I mean, the Mystery Dungeon: Explorers games simply did that. Close second would be Gen III for me, although that's mostly thanks to Emerald and FR/LG and not because of the original Ruby/Sapphire.
I think I'm gonna have to go with gen 3. Kanto and Hoenn have most of my favorite Pokémon which is the main thing. I also really like the "feel" of both of those regions, including the Sevii Islands which I think are really cool even if there's not much to them. I sort of miss the game mechanics of that era too, although the physical-special split was probably a good change overall. Johto is still my favorite region, and gen 4 comes in a close second.
It's hard to say, really. I think Gen V is probably the best overall, but I also have really soft spots for Gen III and IV. IV started out rough, but I'd say HGSS is maybe the best game in the series. III lacked some of the quality of life changes brought later but it was really enjoyable especially if you include spin off titles.
Ask me a year ago and I would have said Gen III above all others. But I think that was just the nostalgia talking since Ruby and Sapphire are what brought me back into the series after GSC bored me out of it. These days Gen V has taken the mantle as my favorite of the series as it probably should have eight years ago. After all, it was around Gen V's release that I made an OC for Unova to use in RPs. I haven't done anything like that for any other region and I still jump at any chance I can to use the character even to this day. What's more, BW and B2W2 have the best story out of any other Pokemon game as well as the best music. N's Castle is by far my favorite track in Pokemon so much so that I wish you could create save states in Pokemon games so I could have a backup file to replay that particular part of the game over and over again. B2W2 had the most expansive post-game with exploring the rest of Unova, the White Tree Hollow/Black Tower, and of course the PWT. Knowing me, Gen III will probably reclaim its crown once I do anything Hoenn related but for now Gen V is my number one.
I very hard choice, that I don't think I can make, as it constantly switches.
A good tie between Gen 2 and Gen 7.
Gen 2 because along with nostalgia, I really loved the region of Johto, and a lot of the Pokemon in it. I loved a good handful of the characters. It felt like it had a lot more story than Gen 1 (I usually don't mind simple stories in Pokemon games, but gen 1 basically had nothing). It was a really fun generation to get introduced to the Pokemon games with. I also loved the anime a lot.
Gen 7 because I absolutely loved the story, the characters, and the Pokemon. Sure, there were things about the games I don't like, but for the first time in a Pokemon game I felt a dire need to complete the story because I wanted to help Lillie and Gladion. Sun and Moon has some of the best characters in the franchise, and that alone puts these games up high for me. The Pokemon, though not too many new ones, were really well designed and I loved them.
And while it is too early to judge as the games are not even out yet, I think Gen 8 is going to be really high on my list.