I recently restarted the Gen 1 and 2 games and actually, after a play-through, I must admit that Gen 2 was rather poor.
Generation 1 flowed well, had great Pokemon and great music. The entire region was well-made and for the first time out of all the times I've played Pokemon, I was suddenly struck by just how goddamn useful the Bug type was.
Using almost purely my Parasect which knew Leech Life (and was several levels behind the trainers and especially the gym leader) I steamrollered the Saffron city gym. Only a short while earlier with my Fearow I had similar beaten the fighting type gym.
It really stood out when I played Platinum later how I had to train for ages so that I could be sure I would be able to beat the gym.
Very few Pokemon were bad in Gen 1, with Lickitung being the only one that springs to mind. Admittedly, the ghost type was a supreme novelty, being so limited and useless against the only Pokemon they were meant to be good against.
Generation 2 was less enjoyable.
While the addition of the Steel and Dark types - along with the switching of various moves and the Magnemite family's types - were welcome, some of the new 'Mon weren't. Gen 2 was fun, don't get me wrong, what with the Time system, berries, Aprikorns, Bug contest and so many other things - not to mention the music - but... playing the game, no matter how enjoyable with the brilliant music it had, was horrible just by thinking about the awful, so-called 'baby' Pokemon.
Most of said 'mon were useless; Togepi's best move was Metronome, and Pichu was just a waste of time. It didn't help that they had to evolve through 'Happiness' which meant you had to waste money on improving an invisible and almost pointless stat until you were confident enough that the next time you wasted time and Exp levelling the damn thing it evolved into something marginally less useless. Hell, after in Gen 1 when my Magikarp won the battle against my rival, I can safely say that baby Pokemon are the most useless things introduced.
The region also, while well placed in general, was badly made. I almost avoid the 2nd town (which the name of has evaded me; presumably because the town was pointless and essentially only good for the Centre and the Town Card, which weren't really needed anyway...) simply because the 'sea' area looks as though the sharp edges of the 'beach' would do more damage than above mentioned baby 'mon. It was horrendous.
There were even more awful 'mon as well, not to mention more novelty ones. Stantler, Girafarig, Murkrow and Misdreavus all sounded cool but ended up being ignored because they were awful. Others, such as Dunsparce, Yanma and Ledyba (no one even mention Shuckle *shudder*) are sheer abominations.
But the music was good.
Gen 3 was the best, because not only did the remakes bring back all the good old feelings in better graphics and redux the music (although Bug still remained useless), it also brought it some really worthwhile Pokemon (Poochyena; Pure Dark Type, Sableye; No weaknesses!, Shedinja; supreme novelty, MUDKIPS; need I say more?) , not to mention a meaningful storyline for once.
The music was good again too, since the creators had more lenience due to the GBA's increased capabilities, though it was quite lacking sometimes as only some of the areas retained the hummable and catchy tunes which were what I loved most about Gen 2.
The chief fault in my opinion with Gen 3 was that they introduced too many legendaries. As per tradition they introduced a new group of 3 (Regirock, Regice, Registeel), a new Mew-like 'mon (Jirachi) and even a new Mewtwo-like 'mon (Deoxys). They then introduced a further 5 (Groudon, Kyogre, Rayquaza, Latios and Latias) which, while the first 2 influenced the plot to a large extent, and Rayquaza rounded them out, the last 2 felt like throwaways, as though Nintendo just wanted to get as many Pokemon as they could and decided to make them into what wasn't even a semi-plot.
The worst generation is easily Gen 4 though, because let's face it: the Pokemon were awful. The vast majority of the legendaries looked dorky (obviously not Dialga or Palkia though, they were awesome) and before the Gen 1 haters 'compare', when compared the the first generation of legendaries or indeed any other set, they look even worse because those generations proved that Nintendo could make decent Pokemon but just hadn't bothered this time. The region is forgettable, the music mediocre. The first time I played it (on a rom of Diamond), I got lost halfway to the second gym and somehow ended up at the Pokemon contest hall upon which I attempted to understand the new contest mechanics, failed and deleted the game. Even on a second play-though (although obviously, after the 2nd gym everything was new to me) with Platinum, I found I had to frequently check my town map to make sure I was going towards where I wanted to go and hadn't somehow skipped another gym. I won't even mention the awful Pokemon (although that utmost evil, Shellos just makes me feel sick; anyone who says it's cute is screwed up), but I will at least note one good and misunderstood point of Gen 4; Bidoof. Everyone seems to hate it and yet (although this may be influenced by Pokemon Mystery Dungeon) I just find it awesome, but sadly not it's evolution.
The underground was fun too, but lost it's point since somehow without ever using it or mistreating my DS I've managed to epically break my Wi-Fi; it only works when my DS is pointed at my computer's internet cables (when the DS is right next to it, I might add.)
I was happy at first when I heard about the Gen 2 remakes; the expanded game compared to others made it worthwhile and the DS's graphics would put an end to the above mentioned block-beaches.
Most of all, I was expecting the music to be remade fantastically. It wasn't ~ Enough said.
Wow... I went on for a long while hee hee.