It’s impossible to choose! WARNING: SPOILERS TO FOLLOW
Supernatural is a show known for its high body count.
Sam and Dean have each died at least a few hundred times.
But they always come back. Most of the others we’ve lost haven’t been so lucky, and if we ever see them again, it’s through dreams, ghostly visits, or trips to heaven.
Characters are listed in reverse chronological order of their [most recent] death: