Rank the Pokemon Generations!

[Jarlaxl]

So I dug up my old Pearl cartridge recently, since I realized that I had never beaten it and I really wanted to take a crack at taking down Sinnoh's Elite Four.

I'm a lifelong Pokemon fan, and, since I haven't booted up a Pokemon game in a while, this got me mentally ranking my most to least favorite generations.

I'll even share the fun with the wacky, fun-loving Escapist community - rank them on whatever metric(s) you see fit.

1.

Spoiler

1. G/S/C (2nd Gen) - I'm generally a sucker for sophomore acts, and I'm wondering if, deep in my psyche, this might be why. They gave you Johto and Kanto to explore, there was a great mix of old and new guys, the designs felt very similar to gen 1 while having their own distinct feel, and they added a *TON* of new (and, most importantly, relevant) content - babies, breeding (my personal favorite), berries, a day/night system, held items, dedicated genders, 2 new types, my favorite legendary trio (Entei <3), a memorable amount of side-quests and content, the feeling of a continuous world - overall, it was basically everything there was to love about Pokemon with a big fat bow on top.

2.

Spoiler

2. B/W/etc. (5th Gen) - So where do you go after making Arceus, God of the Pokeverse? You start over. That's exactly what happened in Unova, but, more importantly, it really shows that they brought 4 generations of expertise to bear on this one - it's just so polished. True, a lot of the new stuff felt kind of tacked on (triple battles...), there are way too many legends, and I could definitely critique some designs (but absolutely no critiquing Darmanitan, Bisharp, Sawsbuck, or Bouffalant), but it just feels like they learned how the game should work, how to build a region, and how to start sort of caring about the plot of the universe beyond, y'know, kid takes on villainous organization while becoming a Pokemon master. In my mind, they improved a lot, trimmed out a lot of the fat, and added relevant new stuff. Plus, they limited who was present in this universe to new guys - but if you look at them carefully, many of the new guys mirror the first gen pretty neatly, so everything's different, but everything's the same. Add in the fact that it's damn good-looking, and I was ruthlessly impressed by this game.

3.

Spoiler

3. R/B/Y (1st Gen) - Technically (and when I say technically, I mean in terns of technology), this game was the weakest. But...come on, I can't really let it dip much lower than third. You never forget your first, and Squirtle will *always* be my homeboy. Me, Blastoise, Butterfree, Beedrill, Raichu, Allakhazam, and Pidgeot roll deep. Memorable gym leaders, an anime that was basically a third parent, the scary-as-balls Mewtwo, that freaky Lavender Town MIDI, the first movie, rumors of the truck and Mew, MISSINGNO...there's too much good in this generation and there are too many positive experiences with this generation to let the flaws detract.

4.

Spoiler

4. D/P/Pt (4th Gen) - I hate to rank this one so low, but I must. Let's ignore the fact that contests are back and there's a bunch of superfluous nonsense in this one (Poffins? Go away). This game did one thing incredibly right but two things incredibly unforgivable. What they got right: new Attack/Special Attack Split method! Good Lord, I had wanted them to do this since Gen 2. Suddenly, the game started making intuitive sense, and dudes who were bad for all the wrong reasons started being much, much better. I wish I could say that was all this gen added and the world was at peace, but, alas, that is not the case. What was unforgivable is only really so if, like me, you're primarily interested in Pokemon for the single-player game (to hell with competitive battling, Smogon is for dorks): (1) the distribution of Pokemon over the course of the single-player game NECESSITATED you take Chimchar or risk having a team so underpowered it hurt (no, Ponyta is NOT a viable fire-type), and (2) ZUBATS AND GEODUDES?!? ASDFGHJKL; AAAAAAAAAAH

5.

Spoiler

5. R/S/E (3rd Gen) - Look, I'll grant that Gen 2 was a tough act to follow, bu this was NOT the way to do it at all. They gutted damn near all continuity with the prior games (gen 2 led us to believe that they wouldn't), any additions they made felt very tacked-on (contests, natures, and poorly implemented 2-on-2 battles, oh joy - but abilities were pretty decent once they went beyond kind of silly tacked-on things and actually gave Pokemon a lot of flavor, like Shedinja or Kecleon), and a general feeling of "we're not sure what direction to take this franchise in!" really rubbed me wrong. Add in the fact that there was just too. Much. Water., and the problems compound - there was one point in this game where I had 3 water-types in my party just because they offered decent type coverage and I desperately needed spots for water-based HMs. Still, most of my favorite designs are in this generation - Absol, Altaria, Sableye, Volbeat, Illumise, the fossil families, Aggron, Medicham, Camerupt, Spoink, Flygon, Cacturne, Breloom, and Seviper - I just wish that they came in a better package.

 

[Smeggs]

This is extremely difficult. To note these are based not on something just like Pokemon design, but overall design of the region, story, feel, etc, and mostly this is dependent on how I connected with the games on whole, not just "DIS ONE IZ BETR!"

Spoiler

Johto In General

Second generation has some of the best designs in the series, but that's not what I'm going to talk about. I think that the Johto region was just better in general. It felt more organic, I suppose is the word I'm looking for. Next to every other generation, Johto feels the most like a natural place, followed closely by Hoenn. Kanto, Sinnoh, and Unova are all very industrialized to varying degrees, while Johto is filled with small villages and towns and large (in game terms) expanses of natural wilderness, except for Goldenrod, but even then Goldenrod has its own National Park for the preservation of nature, and is surrounded by forest on both ends. I've never really been big on huge cities, so Johto's more country-style design fits me perfectly.

Spoiler

Generation 3

Like I said, I have a soft spot for more open, rich locale. It might just be that this was the last game I'd played back when I still had that magical childhood splendor of mine. To be honest Generation 3's designs were quite a bit ho-hum. There were some good and some bad, but mostly they seemed...bored? Don't get me wrong, I love me a good Shroomish or Tailow, but they just seemed sort of bland. However, the story in these games was the most adventurous so far, and the music reflected that nicely with its riveting (sometimes slightly overused) french horns. Taking you from your little quiet village to the bottom of the ocean. This is also the only game that has really shown what will happen should evil win, causing horrible floods and rainstorms or a vicious, unforgiving drought. Even though Team Aqua's was a bit derp when compared to the slightly more sensical ideals of Magma. Also, Blaziken 4 Life.

Spoiler

Generation 5

The map was still great, even if I don't quite like huge cities, it was saved by the dynamic camera angles that it took.

And they finally stopped doing that thing in the GAMES where all of the IMPORTANT WORDS and NAMES were CAPITALIZED for EMPHASIS. So now when I have a LOWERCASE NAME it doesn't look weird like in OLDER GENERATIONS where everyone's names are in ALL CAPS.

Story Rant:

I don't care if someone wants to complain about the Pokemon designs right now, but if anyone actually tries to argue that generation five did not have the best writing or story out of the competing four generations...just stop. The writing and story of Black and White were on a new level compared to any of the previous games, and this should be plainly easy to see by anybody with an attention span of longer than five seconds. This generation has set a bar that will need to be either met or raised in writing for any games following it.

They even dealt with the long-beaten idea of whether or not it was morally right to use Pokemon to do battle and other things, and the notion that it may not be the best idea to let your child who has never been away from home/just moved to this region go off on their own for a country-wide adventure, along with some other things. Bianca was still annoying, though. Cheren was finally a good mixture of Gary Oak and Silver. Finally we had a rival who was not simply an angry douche, but not just some annoying child/best friend. Cheren was driven by the player, and the player was driven by him, to grow stronger. The champion of the region himself even recognizes and acknowledges this at one point in the game. At one point Cheren loses sight of anything but becoming stronger, and it basically becomes your job to show him that that way of thinking is bullshit.

You run into the antagonists a lot more, and you actually see the gym leaders DO SOMETHING about the evil organization rather than sit on their asses. You also get to see Team Plasma's plans nearly come to fruition, as their castle base destroys the Pokemon league while they try and take control of the region from atop the league plateau.

Ghetsis is easily the most evil of all the organization leaders of the games. Let me break it down for you:

-Tries to con people out of their Pokemon with guilt trips, all the while actually planning world domination.
-He took in N and kept him more-or-less locked in a room for most of his childhood.
-During this time, he only had human contact with two beautiful women, one acting as sort of a mother and one there as a "comforting figure," which honestly could be taken in MANY different, very depraved ways.
-The only pokemon that he met were selected by Ghetsis, and were ones that had been abused by their trainers, to make N believe that all regular trainers were hurting their Pokemon.
-He BRAINWASHED this child and sheltered him from the world, ruined his life, and all just to further his own heinous goals of using his purity to gain control of one of the two legendary dragons.
-At the very end, when N fails to defeat you with the power of the dragon, Ghetsis disowns him, pretty much calls him a failure and disappointment, and then tries to KILL you-the player only being saved as a spiteful N steps in and throws you a full restore. And let's be serious, every other evil leader just didn't have the same threatening, coniving, decietful, vile attitude that Ghetsis did. They would not have been able to kill a child, they were just too goofy. Even Giovanni had morals, he lead a gym, and after being defeated put himself into exile (And, according to some rumors, may have committed suicide after you defeat him in the HG/SS event he was in, drowning himself when he realized that you had again stopped Team Rocket).

TL;DR

The story is the best draw of this game, though I do like many of the Pokemon. More exciting designs than Generations 3 or 4, in my own opinion.

Spoiler

Generation 1

"WHAT?! GENERATION ONE IN 4TH?! RAWR-RAWR-NOSTALGIAFAG-"

No. Because Generation One was the first I ever played.

This is not here because I think it is bad, it is here because, honestly, its age shows. I'm not going to speak on the classic Pokemon, some are great, some are bad, some are derp, just like every generation has. It's just that the map is kind of boring. I mean this game was the bare bones that all following generations have been built upon, so it shouldn't come as a shock, and honestly this generation gets props for being the grandpappy of all Pokemon games.

It's still fun to play, but the gen one games are more of a, "I just feel like a runthrough," as that's all there is to the first generation. Just the basic training, grinding, and leveling. There really is nothing more to it. Bare Bones Pokemon experience. Not a bad thing, but the formula was improved upon.

Spoiler

Generation 4

Hate Ahead-Turn Away, Sinnoh Lovers.

I still dislike this one. It may be a bit biased, as I feel I may have ruined it a bit for myself by looking at some of the Pokemon before it came out, but still. The dialogue was horrible, obviously in this gen specifically aimed toward the child demographic, as it honestly made me feel like GF thought I must be some sort of moron who drooled from the mouth with some of it. Not only that, but the game felt somewhat dead. I dunno if it was the color palette or just what, I think it may have been the fact that it seemed like most of the map was dirt/rock brown or boring city-gray. Team Galactic also had to have the dumbest outfits and hairstyles of any of the evil organizations in any of the games, even topping Team Magma's goofy cult robes.

Nothing says evil like cyan bowl-cuts and...oddly go-go dancer outfits. Don't get me started on the execs.

This generation may be the reason I loved Gen5 so much, as in my eyes it would not have taken much to improve on Generation 4.

The fact they had a large group of previous generation (mostly one and two) Pokemon in the game bored the hell out of me. Seriously, of all things, why did you have to bring back the cave-swarms of Geodude and Zubat?
When people want to talk about stupid Pokemon design I'm surprised how most want to complain about the newest gen and not the attrocities brought to us by the 4th gen. Bidoof, Cherubi, Bronzor, Chingling...I dunno, most of the 4th gens just didn't resonate with me. I also disliked the starters, Turtwig was the only one I could stand to look at for more than five seconds. I will admit there were some gems; Shinx line and Starly were okay, among some others (Snover/Abomasnow FTW), but it just seemed like the 4th generation was solely aimed at the children with its designs, like GF just went, "Fuck all of our other fans, what do the little boys like...DRAGON-SHARKS! Now what do the little girls like...PINK CHERRY-BLOSSOM CHIBIS, DESUUUU~"

 

[Khazoth]

I watched the first one when I was a child in the 90's. That one is best.

[Adjusts rose-tinted goggles]

 

[Spambot 3000]

Pokemon Platinum, in my opinion, is the best game (so 4th gen). Why? Because it had the best battle factory. And just the right amount of Pokemon available too. I even remember buying every single item possible for my Villa. Good times ...
The ranking of the others:
Gen 3 - Introduces the amazing Battle Factory and it was fun beating the whole league with just Swampert.
Gen 5 - It was a good step forward for the series I reckon
Gen 1 - Good classic feel, even if there was gameplay problems
Gen 2 - Soulsilver was fun, I guess but I hardly even find the generation memorable.

 

[krazykidd]

For me it's :

Gen 2
Gen 4
Gen 1
Gen 3
Gen 5

I really think black/white are the absolute worst . But that's just me . Maybe i'm getting old and tired . I just personally cannot appreciate it .

 

[Metal_Head]

1st. Gen 2 Only because this is the one I sunk the most time into. I felt the rival was the most "evil" and had the best development arc and Lance's battle music was so epic! Plus I had both Johto and Kanto to explore and Conquer.

2nd. Gen 1,since no one forgets their very first choice. Charmander for life! Although I found it a bit short.

3rd. Gen 3. It had more stuff: double battles, abilities. Although the Team Magma/ Aqua arc was, I found, a little lame. Although it had Breloom and Gallade so all is forgiven.

4th. Gen 4. I thought the designs were a little lame, (some of the pokemon in Gen 3 were a little silly.) It seemed like they were running out of ideas.

I haven't actually played B/W yet, I couldn't be bothered trying to catch them all now, considering that there is over 600 now.

P.S I thought that the HG/SS remakes were the very best games so far. All the nostalgia and old pokemon plus an oppitunity to relive it all in new graphics. *spoilers* (I cant do that click to view thing) Being able to call the gym leaders and challenge them to a rematch is one of the best things, and new Elite Four teams after beating Blue was an added bonus.

 

[GiantRaven]

Yeah I think the original post sums up my thoughts quite well. I'd probably put Gen IV on the roughly the same level as Gen V though.

 

[Odbarc]

Diamond/Pearl? Never played it.
5th/5

The original
Replayability is weak. Why? The path never breaks, it doesn't offer you much other than to redo the entire game with a different pokemon or team. I'm TOO familiar with them and I know exactly where guys are, where to get them, what they do, ect. ect.
4th/5

Currently got Black/White and at first I didn't like not knowing any of these new pokemon, I found a few nice ones. I'm absolutely livid about trade-evolution pokemon. That's just a "You can't have this one EVER" type for me.
I like to choose my dopes based on how 'cool' they look versus statistical strengths.
Rank it 3rd/5

Ruby/Sapphire
Added a lot of good stuff. The bad you could skip (mostly) like the crappy berry planting/mixing/ribbons.
It was had finding a good team seeing as a lot of the guys I got were just BAD and WEAK. Just - everything felt WEAK. All my guys almost died regardless of what I put them up against.
My favorite Metagross. How awesome is he?
2nd/5

Gold/Silver
It was like an expansion and a new game at once. It didn't just mix up the pokemon, it just ADDED 100 more. And while there seems to always be those fodder-pokemon in every game it added some of the best additions to a very stale (albeit complex) game.
Held items, shinies, unique poke-balls. None of the other pokemon games did this quite as well. It was the biggest jump forward. While the other games are technically superior, the jumps forward have never matched up.
Maybe this is because the original was such a low bar to surpass.
1st/5

 

[nuba km]

Gen5 - It just has so much more variety in the pokemon designs and types and has very few designs that are plain bad

Gen1 - Similar reasons to gen 5 though there were some very lazy evolutions

Gen3 - Its very different design to gen 1&2 or 4&5 make for both interesting and unique pokemons as well as ones that make me want to claw my eyes out.

Gen2 - While many would kill me for placing this gen so low I will say that it has way too many single stage pokemon that feel like they should have a evolution and most of their pokemon are just too weak to be reasonable to use.

Gen4 - I wouldn't say this gen has any bad designs, but it also has a major lack of good designs most of which are just evolutions of previous gens (including my favourite pokemon dusknoir).

 

[Techno Squidgy]

1. Gen 1
2. Gen 2
3. Gen 3

I haven't played a Pokémon game since Gen 3 and have no real desire to. I couldn't even catch (and in fact still can't!) 150 (mew is pretty much impossible) and I can't deal with the disappointment of being unable to catch 300 odd.

in general, I just prefer the design of the gen 1 Pokémon (Nostalgia goggles, ho!) with Gen 2 being a close second. Gen 3 introduced Mudflips but excluding a couple of others, there aren't that many I like. I know nothing of Gen 4 and 5 Pokémon.

 

[Hjalmar Fryklund]

After some introspection here is the conclusion I came to:

Spoiler

1. Gen 3. I absolutely adore the nature romanticism in Ruby/Sapphire/Emerald, and the soundtrack is sterling. The trainer designs are really neat looking as well.

FireRed is the game I have logged most time into (with a complete Kanto Pokedex) and there are very fond memories there. Shame it didn't have any Johto in it but I guess it was a bleesing in disguise for my grades.

The pokemon designs are quite nice, but I do dislike the way some are drawn. Strangely enough, many of my favorites to use are also ones I consider to have dodgy design.

Oh, it has Spheal. Everything gets better with Spheal. I just wish Walrein was cuter...

Spoiler

2. Gen 2. I think (and I stress think) this is the generation where I really became a Pokemon fan. There was quite a lot to see in them and the rival was fun to fight against (rather than the fairly stale Gary). Co-incidentially, that particular rival was the first instance in manga where me and my friends couldn't tell whenether he was a man or a woman.

The pokemon designs were mostly okay, nothing really sticks out to me though.

Spoiler

3. Gen 4. Sinnoh took quite a step back for me with the trainer designs and the soundtrack (there are some gems though in both cases), hoever it made up a bit for it by making traveling a really pain in the arse. And I am a sucker for that kind of challenge.

The pokemon designs were not love at first sight I am afraid. To put it in a (teeny bit) sensible way, I just don't like the turn that coloration and the drawing of curves and lines took.

It should be noted though that Gen 4 sits at the third spot only because of the Gen 2 remakes.

Spoiler

4. Gen 1. I only played Yellow here and while it was all right (back in the 90s) I really don't find much to in Gen 1. And I didn't think much differently back then either.

Still, with Charmander (all-time favorite) and the Machop line (lovely creepy buggers) it okay at least.

I have yet to play Gen 5, so jugdement has to be withheld there.

 

[Best of the 3]

For me Gen 2 was my favourite. Introduced a lot, berries, Kanto and Joto, more pokémon without being too confusing like later gens, and a few other things. It's been a while since I've played it so I can't remember everything it gave.

Then it'd go 1, 3, 4, and i don't think I've played any others.

 

[mrhappy1489]

Ok so I think I might have to indulge myself and do the full pokegeek thing and describe what I loved about pokemon, because in my mind each is good, but only 1 may rain supreme followed by it's worthy adversaries and no I don't know where this is going.

1. Gold/Silver/Crystal

Gold, oh my what a game it was. This was the first game I have ever owned and aside from Oblivion, the game I have probably sunk the most hours into. Now being in a home that refused video games for most of my childhood, I never played any pokemon games until this and it came as a shock on my birthday that I would receive such a gift. On that day I begun to play and play and play, never looking back, or leaving to go outside, just sitting and playing away at Gold. Now most would say this is nostalgia talking and to be fair, it is for the most part, but one memory that sits vividly in the deepest reaches of my mind is this. I'd just defeated Blue and finally been allowed entry to Mount Silver, being the inquisitive sort, I took it upon myself to venture into the mountain and uncover what mystery lie beneath, or above as the case may have shown. Venturing through the cave, capturing interesting pokemon and generally feeling chills, I couldn't shake the feeling that something big was ahead, I mean the music was that of the Elite Four and that feeling of anticipation grew within me, the same as which engrossed me going into the Elite Four. After venturing to the deepest reaches of the cave, I saw one man, standing at the end of the path, very similar to myself, but just a little different, older it seemed. After saving, I approached the mysterious individual and was greeted by only this ..... Then it was on, the battle screen begun and the character name popped up, RED. Though never playing pokemon red or blue, one would be a fool not to know who stood before me and then the battle was on, Caden vs RED. Red proved to be the strongest challenger ever faced, me lacking any friends who owned or played the game, so I was unprepared for the challenge ahead, I'd never invested in any pokemon, save my trusted Feraligator and we had yet to come upon a foe who could best us. The battle raged for some time, some opponents simple, others not so. In the end, paralysed and low on health, my feraligator bested Espeon and the battle was done, I had won and once again .... was all I received. The victory against Red, the credits rolling for a second time and his absence upon my return, are my most treasured gaming memory and is what cemented my love for pokemon and my continuing admiration for Gold in particular.

2. Ruby/Sapphire/Emerald

While not being as enjoyable as Gold in my opinion (nor its remake to be frank) Ruby is one of the games that I absolutely adore, this time nostalgia not with standing. Whether it was the vibrant colours of the land, a mixture of bright and dark alike forming an immediate impact on my memory or simply the charming soundtrack, Ruby has always been a perennial favourite of mine. Now while this comment will seem out of place, considering it is generally a criticism, what I like most about Ruby, were the small changes here and there, that while creating a different world and experience, still encapsulated the same feeling of grandeur left over by Gold. What I think it did really well, was increase the amount of water present. I cannot speak for all my fellow Escapists, but this inclusion helped create that feeling that we were travelling a vast an expansive landscape, something I have yet to see matched in a pokemon game, even Gold with its dual Johto and Kanto exploration. It also didn't skip on impressive land terrain as well, mixing desert, mountain, forest and grassland perfectly, helping to create a whole world, not just a portion of it. All in all I will always have a special place for Ruby and it's other brothers.

3. Black/White

Hear is a question for you, after 4 games and the literal inclusion of God, what do you do to improve it? That's right, start over again but with a better story. While not trying to ape the OP, I'll skip right to the part of White which made it a memorable experience for me. Now being an avid player of pokemon, there is a single common complaint that while always rain true, that it's story portion is bollocks. Now don't get me wrong, pokemon does a great job of creating a world, great landscapes, enticing battles and of course POKEMON themselves, but when it came to story there has always been something lacking, more precisely, it's basically the same thing over and over again. You start of (1,2), you get a pokemon (3,4), you go on a journey (5,6), you defeat an evil organisation (7,8), you defeat the Champion and defeat the game (9, 10). Now while White didn't deviate stupidly from this, honestly it wouldn't be pokemon if they did, what it did was creating characters that actually felt like characters. Cheren had dreams, ambitions and feelings, he wanted so desperately to claim Championship, but it always fell beyond his reach, no matter how he tried he just couldn't reach it. But he grew, resolve surrounded him and he found new goals and ambitions. N wasn't just some blank antagonist like Maxie or Cyrus, he had real goals and a real reason to go for them. He wasn't just there to fill space, he truly believed what he was doing was right, that he was doing this for the good of pokemon. Ghestis finally, is probably the best antagonist in any pokemon game to date. Rather than being an incompetent fool constantly moving from one base to another, challenging you and failing, he pulled the strings from the background, did his research and played the game like a proper villain. He very nearly pulls it off and for once as well, but was stopped not only by you, but through the combined effort of your friends and the gym leaders. Altogether, what White and Black offered was much more than the standard pokemon game, but one with actual storytelling chops, nearly worthy of that the characterises Nintendo's other big franchises.

4. Diamond/Pearl/Platinum

For my fourth and final game (considering I never owned red or blue, though I did defeat the remake and no all of its pokemon) Pearl, I'll admit this, I played the hell out of it and loved it. But that is all. The problem I think with this game (only played Pearl) is that it was just your simple pokemon affair, providing a fun game and some great pokemon (Garchomp and Lucario) but not offering anything particularly ground breaking or attention grabbing that would otherwise have had me thoroughly invest. All in all it was just a fun experience, but nothing worth writing home about.

Now just to remove some peoples queries, I didn't talk about the pokemon, because I love each generations pokemon equally and praising one over the other is simply foolish.

 

[mrhappy1489]

1. Gen 1
2. Gen 2
3. Gen 3

I haven't played a Pokémon game since Gen 3 and have no real desire to. I couldn't even catch (and in fact still can't!) 150 (mew is pretty much impossible) and I can't deal with the disappointment of being unable to catch 300 odd.

in general, I just prefer the design of the gen 1 Pokémon (Nostalgia goggles, ho!) with Gen 2 being a close second. Gen 3 introduced Mudflips but excluding a couple of others, there aren't that many I like. I know nothing of Gen 4 and 5 Pokémon.

My friend, mew is 151 not 150. I'm obsessive over pokemon so I won't blame you, but if you make the mistake again, so help me god I won't be responsible for my actions. If anyone wants my response it's a little above this.

 

[White_Lama]

Well I only watched/played the games until Gold/Silver was releasedm so I'd have to go with R/B/G/Y versions, whatever Gen that is.

 

[Zealous]

Spoiler: 1st Gen

Horribly outdated. Looks like crap. The battle system and interface are disgusting. Sorry old friend, we shared many a memory together, but you're history now.

Spoiler: 2nd Gen

Arguably my favorite generation (until Heartgold/Soulsilver showed up). Introduced a bunch of my now favourite pokemon, added the dark and steel types and was generally awesome.

Spoiler: 3rd Gen

I played the hell out of Ruby and Emerald and had quite a time with Firered too. However, much like the other two Gens before it, interface, battle system and physical/special designations kill the game for me.

Spoiler: 4th Gen

Best. Gen. Ever. They got physical/special right (FINALY), remade my favourite game and IS generally awesome. I guess Diamond/Pearl/Platinum was okay too.

Spoiler: 5th Gen

Weird art style change, clunky battle system and way to pixelated. The pokemon, story and region are fine, but the game play turns me off of the games so bad.

 

[WinkyTheGreat]

Gen 2: 16 badges, not an overabundance of Pokemon, the first gen in which eggs came to play. Second Gen is by far my favorite

Gen 1: It's nostalgia, but considering I spent hours upon hours playing first gen games, It has to be second for me.

Gen 5: White was the first game that I sat down and was really excited to play since the re-release of HG/SS. I'm looking forward to B2/W2

Gen 4: I got back in when I bought a DS and got a copy of Diamond. It rekindled my love for the games, but wasn't anything truly memorable for me considering the lack of post-elite 4 content

Gen 3: I admittedly never played a Gen 3 game. It was the first gen on GBA (a system that I've never owned) and I was in that "I'm too cool for Pokemon" stage of my life (having just gone into high school).

My only problem with the increasing number of generations is the increasing number of Pokemon. I've always been able to justify overlooking 100 species (from Gen 1-2), but at this point, Prof. Oak overlooking over 400 species just seems ridiculous.

 

[Andy Shandy]

1. 2nd Gen (Gold/Silver/Crystal)
It was bigger and better than the originals, and you could even go back to Kanto, home of the originals and face the gym leaders and all that. Pokemon Silver and Crystal are probably the games that I have put the most time into by a huge margin. Also introduced Skarmory who is probably my favourite Pokemon of them all (as difficult as I remember it being to catch)

2. 5th Gen (Black/White)
There's just something about this generation that I love. Not particularly sure what though. Maybe it's just because it is the current generation, but I do like it a lot and can't wait for Black 2 and White 2. Plus I absolutely adore this track from White's version of Opelucid City. One of the best tunes in the whole series of games, in my opinion.


3. 1st Gen (Red/Blue/Yellow)
Like it was said in the OP, I can't honestly conceive of putting this any lower than 3rd. Still enjoy playing through Yellow on an emulator.

4. 4th Gen (Diamond/Pearl/Platinum)
Don't actually have a proper reason for putting this above the 3rd Gen - especially since I have a reason for liking the 3rd gen - but I believe I just enjoyed Pearl & Platinum more.

5. 3rd Gen (Ruby/Sapphire/Emerald)
While by no means a bad game, and it introduced my favourite legendary in Kyogre, it's just the one I enjoyed the least. It's also the only generation so far I didn't go on to buy the "3rd game" of the generation.