The supernatural portion doesn't take place in any particular season

Sam Winchester : The younger brother of dean, was the vessel for lucifer, has literally been to hell and back, he has medium length hair , dark brown hair and the best puppy eyes ever, they will melt your heart of stone
Dean Winchester: the older brother of sam, was the vessel for Michael (the angel Michael), has also literally been to hell and back, he has normal length hair and amazing green eyes that will melt your insides
P.S: don't touch his pie, he loves pie and his car don't touch his car either

General info:
Both of their parents are dead
They travel the country fighting monsters like demons and vampires (not like the sparkly ones real actual badass vamps)
Angels are dicks and so are demons
The only exception is castiel
They travel in a 1967 black Chevy impala and dean makes Sam listen to classic rock
They know the king of hell his name is Crowley

Castiel: his vessels name is jimmy Novak, he is an angel (but he's not a dick like the others), he has rebelled against his superiors and has fallen from grace and almost died many times , he is the reason dean came back from hell , he has scruffy looking normal length hair that's just a little longer than deans he has blue eyes and he doesn't really understand human emotions but he's getting there

Bobby: basically the boys' father figure, knows a LOT about hunting,
Not much to tell really just know he knows a lot about hunting and is pretty much the boys' dad

Crowley: the king of hell, has owned bobby's soul before, can be a big bag of dicks rather than just one sometimes, and that's about it