- The people of a small town have been selling their souls to a crossroad demon.
- Sam and Dean try to save the life of architect Evan Hudson who sold his soul to a demon so that his wife could live a long and healthy life free of cancer. While Sam protects Evan from hell hounds, Dean is tempted by the demon, who tries to convince him to trade his soul for his father's life, who she claims did the same to save Dean and is now suffering in hell for it.—Anonymous
- When two highly successful professionals die after claiming to be haunted by hellhounds, Sam and Dean investigate the local dive bar and discover it sits upon a site where a deal-making demon has been making people's dreams come true in exchange for their souls. Dean summons the demon to exorcise it but is horrified after it reveals the painful truth about John's death and tempts Dean by offering him the one thing he wants more than anything - his father—Drifa Baljet
- In August of 1938, a blues singer is chased by invisible hounds in Greenwood, Mississippi. Eight years before, Robert Johnson had made a deal with the devil in a crossroad in Rosedale. In the present days, after the death of an architect and a surgeon successful in their careers that had claimed to be haunted by hell hounds, Dean and Sam investigate and find that ten years ago they had made a deal with a demon in a bar to have success in their lives together with a third man. Their further investigation leads them to Evan, the third man that exchanged his soul to save his beloved wife that was dying with cancer. While Sam protects Evan from the invisible hounds, Dean summons the demon in the crossroad to trap and exorcise him. However, the demon tries to tempt Dean offering the life of his father that is suffering in hell.—Claudio Carvalho, Rio de Janeiro, Brazil
- In Rosedale, Mississippi, in 1930, Robert Johnson makes a deal with a demon at the crossroads, asking to be the greatest blues guitarist that ever lived. The deal is sealed with a kiss. In Greenwood, Mississippi, in August 1938, Robert Johnson is playing blues guitar at Lloyd's Bar. There is a sound outside and he leaves, running as he hears dogs chasing him until he takes refuge in a house. Soon after he is found dying, mumbling about the black dogs that are after him.
In the present day, Sam and Dean are researching the case of an architect, Sean Boyden, who jumped to his death from a building he designed. He had previously reported seeing a dog in the building. Thinking this may be a supernatural black dog, the boys decide to investigate and under the guise of writers from Architectural Digest, interview Sean's partner. They discover he had been working as a bartender at a bar called Lloyd's ten years ago, when suddenly he'd shown great talent and became an overnight success.
Dean and Sam start tracking all the complaints about black dogs in the area recently. At the house of Dr. Silvia Pearlman, who has risen to be Chief of Surgery at a young age, her maid confirms the report, and adds that the doctor left unexpectedly a couple of days before. Dean finds a photo of the doctor at Lloyd's. In a hotel room, Dr. Pearlman screams as she is attacked by an invisible dog.
Sam and Dean go to Lloyd's Bar, which is situated near a crossroads. The intersection is surrounded by yarrow, a plant used in summoning rituals, and at its center they dig up a tin containing a vial of graveyard dirt, black cat bones, and the photo of George Darrow. They realize that the black dogs are actually hellhounds which are collecting souls due in payment for deals with a demon.
The boys visit George Darrow, a painter, who admits to having summoned a demon ten years ago and made a deal for artistic talent. After the deal, however, the demon stayed at Lloyd's Bar for a week and made deals with Sean Boyden, Silvia Growman, and a man named Evan Hudson. George is resigned to dying and the boys leave him to his fate.
At Evan Hudson's house, he admits to Sam and Dean that he made a deal with the demon to save his wife from dying of cancer. Dean suggests he go and summon the crossroads demon and try and exorcise it, while Sam protects Evan. Sam is wary of the plan -- like Dean he has been wondering if their father made a similar deal with the Yellow-Eyed Demon for Dean's life, and he is wary of Dean's motives. But as they hear the howling of the hellhounds, he agrees to go along with the plan.
Dean summons the crossroads demon and tries to lure her into the Impala, which is parked over a devil's trap. When she realizes the trap she begins to taunt Dean about how much he has suffered since John's death. She offers to bring John back, in exchange for Dean's soul to be claimed in ten years' time. Just as it appears Dean may make the deal, the crossroads demon realizes she is under a devil's trap painted on the water tower she is standing beneath. Meanwhile Sam and Evan stand inside a protective circle as the hellhounds approach.
The demon refuses Dean's offer of her freedom in exchange for Evan Hudson's life, so he begins to exorcise her while Sam and Evan desperately try to avoid the hellhound. Finally, the demon relents and with a kiss to Dean, breaks Evan's deal and calls off her hellhound. While Dean initially considers continuing the exorcism, he instead keeps to his deal and breaks the Devil's Trap. The demon taunts him about John's fate, but before he can do anything to it, it flees its meatsuit, leaving behind a confused young woman.
Back in the Impala, Sam and Dean talk about the deal their father made. Dean feels undeserving and while Sam tries to convince him otherwise, he asks whether Dean considered accepting the crossroad demon's deal. Dean doesn't answer.
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