GSC feel just like a 90's anime. Silver is the tropey edgelord, Whitney is the cute but whiny brat, Lance is the badass who helps you stomp out the bad guys, Red is the overwhelmingly powerful trainer, etc. Even small moments like Lance demolishing Silver in battle and shutting down his nihilistic worldview about Pokemon, it feels like it came right out of YuYu Hakusho or something. This is a feeling that other Pokemon games fail to replicate. And I am talking specifically about GSC; the feeling was kind of lost in HGSS.
I feel like the gen 2 games don't enough praise in this regard.