My favourite series is definitely Adventures.
As a kid, Devimon was actually scary, the way he was portrayed and easily separated the kids as they slept (although he could of just killed them then and there). He represents real nightmares, turning even friends against them.
Etemon, comedy and brutal, he could de-digivolve the digidestined's digimon with just a song.
Myostismon, mysterious and almost as scary as Devimon was portrayed, taking to the real world and entrapped an entire city, true mastermind who, when killed, returned as a senseless beast. One of my favourite cartoon bosses of all time.
And then the horsemen of the apocalypse along with Apocalymon himself.
Metalseadramon representing Conquest, the take over of the digital world.
Puppetmon representing War, weapon collections, playing a game called war, childish and only wanting to kill.
Machinedramon representing Famine, a world of machinery and buildings, food scarce.
Piedmon representing Death, turning the digidestined into dolls to represent soul collecting, instant kill moves.
Apocalymon wanting to take out the entire world due to the suffering and pain that has been caused.
All the series have deep meaning hidden within them somewhere, but this series means so much to me. Adventure 02 however, ruined so much for me, especially the Myotismon storyline.
Also Wargreymon and Gatomon are my favourite digimon :p