I still remember how crazy everything was when Pokemon was first introduced. I remember my friends at school LOVED the game at the time, and were constantly asking me how many different kinds of Pokemon I had caught in the game. Then, when I entered middle school, no one would be caught dead playing Pokemon. That's when I first saw the stigma attached to it. I understand that the TV show hasn't helped. It started out okay, but has gone downhill, and I can't wait until it ends. However, even though I don't always openly admit it, I always get a feeling of nostalgia when I play any of the classic Pokemon games. They were a part of my childhood, and personally, the only reason I don't play the newer games is because they keep adding at least 100 more Pokemon every time a new game comes out. Then they have to add a new season of the TV series to accommodate it. It's really become more of a gimmick than anything else, and maybe if they had stuck to what made the games great without relying on the marketing, there might not be as much of a stigma attached to it.
As a side note, my favorite generation of Pokemon was Gold/Silver. While I did enjoy the classic Red/Blue game, the addition of the PokeGear and the real-time day/night feature enhanced the experience for me. I also loved going back to the original Kanto region from the first game. Despite fond memories, I'm probably not going to pick up Soul Silver. While I might have done it years ago, I'm 19 years old now, and it would be too awkward for me walking into the store to buy it. That's what the stigma has done. I guess I always have the original Gold/Silver to fall back on, though.