Crossroad is the eighteenth episode of Supernatural The Animation.
Dean is still thinking about the loss of his father John and Sam believes he has become obsessed with the demon. Meanwhile, Sam and Bobby discover a case of a man who, before dying, spoke of his fear of being chased down by a wild hound.
Through their investigation, Sam and Dean discover that people have been selling their souls in exchange for various desires. One man, Evan Hudson, specifically sold his soul to save his wife, which leads Dean to realizing that John may have done just that in order to revive Dean.
This leaves him visibly distraught, since it means John have surrendered himself to the very being he had been hunting for most of his life.
Regardless, the brothers decide to rescue Evan from his deal. While Sam stays guard in case the hellhound comes, Dean confronts the crossroad demon to whom Evan sold his soul. The crossroad demon tries to tempt Dean into wishing John back, and although tempted, Dean decides to force the crossroad demon to free Evan of his contract, unless she wants to be exorcised.
The plan works, and Evan is set free from his deal. However, the demon informs Dean that he had basically chosen to save a stranger instead of his father, and thus left his father to suffer great agony in Hell.
Dean breaks down and cries in the rain over this revelation, while Sam watches on.