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: Played by horror legend Robert Englund (Freddy Krueger), he is an old friend of John Winchester who helps Dean "die" temporarily to meet Death.

: Despite Dean failing the 24-hour test, Death retrieves Sam's soul anyway, noting that he wants the Winchesters to continue investigating "souls" and Purgatory. He places a "mental wall" in Sam's mind to block the memories of Hell. Key Characters & Guest Stars

: Sebastian Roché assists Sam in his attempt to remain soulless.

: Dean fails the challenge after sparing a young girl's life, which causes a ripple effect of unintended deaths. This teaches him that the natural order cannot be subverted without consequences.

: Julian Richings returns in his iconic role as the Horseman.