>>32654790red/blue are fun for nostalgia purposes but replaying them now gets really old quick.
gen 2 is fun for a bit, but has serious level scaling and balance issues as well as no post game.
Gen 3 has one of the most enjoyable storylines and in-game play throughs of all games, has plenty variety of pokemon, and the emerald battle towers are honestly enough post-game content to keep you occupied.
gen 4 is pretty good too, but playing on the DS is really laggy. Platinum fixed most of the lag but even then I find it a chore to replay.
Everything, and I mean EVERYTHING after gen 4 is boring, dumbed down, and just straight up not fun to play through more than once.