I personally have played every pokemon except B&W a few times and I must say, I really felt that Gen III was the weakest Gen. I'm not considering B&W because that by itself is another series, more intent on starting over. Gen I and Gen II were definitely the best with riveting stories, cool pokemon and moves, and the only games where Shinys were awesome, not just art-wise but stat-wise (look it up). Gen IV I really enjoyed actually because even though its story was average, I felt it's extended version game (Platinum) was breath-taking visually, a more vamped story, and beloved pokemon from all over the series available in the wild. So Gen IV gets a "****** enough to not be belittled by me".
I thought the anime was relatively fun to watch until we hit Gen III, when we lost Misty and Brock's pedo ways were a bore. Also, their awesome battle music was missing so that doesn't help.
I played many pokemon games starting from blue,red & yellow and stopped to leaf green and fire red.. the series I have seen some but haven't been busy watching all of that, but I watched all the movies though