I am an average enjoyer of the Pokemon franchise and these are my opinions.

Sir Pentious

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Red/Blue/Yellow: Classic games. They had a minimal plot, bland setting, and many glitches, but were very advanced for their time. Firered and Leafgreen are, however, the more definitive Kanto experiences for those who want to get into the games.

Gold/Silver/Crystal: Brought a much more unique setting with many new features that are now staples of the franchise, including breeding, cross-generational transfers, shiny Pokemon, held items, and more. It even manged to fit a whole second region! In a gameboy color cartridge! Even if many things had to be culled to fit it in, it's still cool that we got this in the first place. And Johto was improved even more with walking Pokemon and so much QoL improvements in Heartgold/Soulsilver.

Ruby/Sapphire/Emerald: Put a bit more focus on the evil teams... or two of them, rather, in a fun twist to keep things fresh. Abilities, contests, and new types of Pokeballs were added, and the generation saw the first remakes. It was a rather large technological leap, and miles better than the previous games.

Diamond/Pearl/Platinum: These games saw the first wifi features, allowing for people all over the world to battle and trade Pokemon with each other. These additions played a big part in shaping the competitive meta, too.

Black/White/Black 2/White 2: There was more of an emphasis on story in these games, leading to the creation of a wonderful narrative. This generation brought the most new Pokemon of any before or after, and pushed Pokemon to new heights with semi-3D graphics. And almost everyone can agree that Gen 5 has the MOST slapping music. Plus direct sequels? Big score in my book.

X/Y: 🤫

Sun/Moon: Took a break from the standard 8 gym sequence, and introduced new challenges in the form of trials. Some banger Pokemon designs came out this gen, including Minior, Rowlet, and Meltan. Ultra Space and Ultra Beasts were interesting new additions to the lore of the series.

Sword/Shield: It was a fun treat to discover that Galar is based on my home country, England! And there were many neat easter eggs and visual touches sprinkled throughout to make it feel much more like the Pokemon equivalent of the UK. The exclusion of the National Dex really isn't too bad when you get down to it, especially since over 400 Pokemon are in the game already when DLC is included.
 
"RBY bland plot"
I thought Pokemon was the first of its kind to collect & battle monsters? Pretty remarkable imo

"XY"
Hey that's my favorite gen, it has very socially progressive npc's, such a great comfort.

Agreed with the rest.
 
"RBY bland plot"
I thought Pokemon was the first of its kind to collect & battle monsters? Pretty remarkable imo
Not even remotely.

Digital Devil Story: Megami Tensei, the first entry in the Shin Megami Tensei series (well first video game entry since the series began as a trilogy of novels), features the ability to negotiate with and recruit demons you fight against into your party and use them in battle, which is one of the key elements of the entire SMT franchise.

Digital Devil Story: Megami Tensei came out in 1987 and is the first game ever to have the whole 'collect and battle monsters' element in it.

Similarly, Dragon Quest V, which was released in 1992 for the Super Famicom, has a feature where certain monsters (40 in the SFC) will offer to join your party if it's strong enough after a battle and you can battle with them and level them up just like the human members of your party.
 
"RBY bland plot"
I thought Pokemon was the first of its kind to collect & battle monsters? Pretty remarkable imo

Even if it was novel for its time, it isn't today. It's by far the simplest generation... and it is also the most recycled. Actually, what made RBY stand out upon initial release is the thing that it was most advertised for — the link cable compatibility (you can even see it in its advertisements). These days, that concept is archaic at best.

Every other region has something about it that stands out and gives it unique identity, but Kanto is sorely lacking in that department, especially when Kanto's elements are constantly brought back every generation.
 
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