Why play classic Pokémon now?On the surface, the Pokémon games before the GBA era appear to be far too outdated to enjoy nowadays. Many of the commonplace features present in newer Pokémon games didn't exist in generations 1 and 2, such as natures and abilities. The graphics are 8bit and far less detailed than their modern counterparts. Numerous people find the likes of RBY (Red, Blue, and Yellow versions) and GSC (Gold, Silver, and Crystal versions) to be pointless to play so far out past their release. This brings into question - why would you want to play games so old? To answer this question, some context as to the history of Pokémon's development in the 90s is incredibly insightful.
In the early to mid 1990s, Game Freak was a tiny company that survived financially through means of developing smaller games on the side1 to support the development of Pokémon Red and Green versions, later released as Red and Blue internationally. By the time Red and Green had released in 1996 in Japan, Pokémon had been in rocky development for six years due to lack of funds, small number of employees, and the programming troubles of a fledgling game studio. No one was sure if Pokémon was going to become the wide-reaching success it ended up being, both in Japan and with the colloquially dubbed "Pokémania" in the late 90s overseas. Despite this, Game Freak started development on Gold and Silver directly following Red and Green's release, which was heavily accelerated and pushed to even greater heights with the financial and popularity returns of the previous installments, eventually getting released after three years of development in 1999. Tsunekazu Ishihara, once a producer of Red and Green and now CEO of The Pokémon Company, stated in an interview, "After we released Red and Green, we began working on these titles, thinking that the ultimate in (sic) Pokémon games could only ever be Gold and Silver... So for me, Gold and Silver represented the finish line... I didn’t intend to make any more Pokémon titles."2 By all accounts, Pokémon Red and Green were the games that got Game Freak's foot in the door, and Pokémon Gold and Silver were the company's ultimate vision of what Pokémon was and could be, once they had the funds and resources to produce games of their caliber.
All of this is to say that Pokémon Red and Green/Blue and Pokémon Gold and Silver are the closest one can get to Game Freak's original vision. As a result, both generations of Pokémon games are very much a core J-RPG experience, inspired by the J-RPGs of the era that they were developed in. In fact, Pokémon almost wasn't localized to America because J-RPGs were known to flop in the west, and they only moved forward with localization due to its Japanese success.3 Consequently, as Pokémon became a worldwide phenomenon, over time, starting with Ruby and Sapphire on the Game Boy Advance, Pokémon's gameplay has slowly morphed away from that original experience into something more streamlined for anyone with even just a casual interest in video games. To many, this is a change in the right direction, but for fans of J-RPG styled gameplay, or even just those looking for a vast and in-depth singleplayer experience, the first and second generations of Pokémon games remain as one of the closest, if not the closest a person can get to that experience in a Pokémon game.
The effects of this original design philosophy resound throughout RBY and GSC. The lacking of new, more complex mechanics such as natures and abilities in modern Pokémon games is made up for with gameplay that requires dedicated time and effort to reach into its deepest crevices. You have to go out of your way to optimize your Pokémon, to max all their stats in a time where EVs didn't exist, to plan and build their movesets, and to get every bit of customization on that Pokémon. Along the way, RBY and GSC, more than any other games in the series, give you the time and space to really get attached to your Pokémon and your individual story as a Pokémon trainer. GSC especially are much slower paced than modern Pokémon and expect you take the time to immerse yourself with a combination of daily events and tough-to-reach goals. It is simple enough for a child to pick up, but deep enough that you can spend hundreds of hours even after clearing the main story just picking away at optimization and teambuilding daily, whether it be to defeat Red, to clear the Crystal battle tower, or 100% complete both Stadium games on the N64. That isn't even to mention the level of customizability that opens up when game versions are connected to each other for trading and breeding!
Many people don't know that RBY and GSC have this level of depth. There's a variety of reasons for this, but one of the main ones is the Virtual Console releases of RBY and GSC on the 3DS eShop. Removed from their original contexts, not only were they not released alongside re-released Stadium games which essentially serve as dozens of hours of postgame for both generations, but they were released so far out from their original 1990s counterparts that many modern Pokémon players tried to play them in the same way you'd play a more modern Pokémon game, such as Pokémon Ultra Sun and Ultra Moon on the same console. RBY and GSC were never meant to be played in this way, and as a result the experience is lacking. However, if approached with the mindset of a fresh and different Pokémon experience, very unlike the ones since the GBA era, Pokémon's first and second generations can be some of the most fulfilling and in depth Pokémon experiences there is. Besides, even as just a look into Pokémon's origins and the mindset of the team in its history, it's worthwhile to play it casually just as a curious Pokémon fan.