So Mary dies

Then Jess dies

Then John dies

Then Ash dies

Then Sam dies

Then Dean sells his soul

Then Dean dies a lot but not really

Then Henriksen dies

Then Bela dies

Then Dean dies again

Then Dean comes back

Then Pamela dies

Then Adam dies

Then Castiel dies and that kinda kills Jimmy

Then Ruby dies

Then Castiel comes back (debateable Jimmy)

Then Jo and Ellen die

Then Sam dies but gets brought back

Then Anna dies

Then Dean and Sam die but get brought back

Then Gabriel dies

Then Adam comes back

Then Adam gets possessed

Then Sam gets possessed

Then Nick dies

Then Castiel dies

Then Bobby dies

Then Lucifer dies - killing Sam

Then Michael Dies - killing Adam

Then Castiel and Bobby come back

Then Sam comes back

Then Misha dies

Then Kripke dies

Then Balthazar dies

Then Castiel dies

Then Bobby dies

Then Castiel comes back

Then Dean and Castiel go to Purgatory but don't worry they get out

Then Samandriel dies

Then Henry dies

It's really good I promise