Dean confronts a Crossroad Demon who makes him a tempting offer.
The episode opens in a low lit bar. A black bluesman is on stage playing his guitar, holding a cigarette in his mouth. He glances casually at a young black woman in the audience. Suddenly he hears growling from outside and stops. However when he stops playing, the growling stops. He continues to play but every few seconds, the growling would start again, and each time he heard it, he would stop playing. He suddenly notices a large shadow figure dash by the window outside. He drops his cigarette to the ground and darts out the door with his guitar still in hand. The bluesman runs down a dark road, dropping his guitar in a panic. He rushes homes bolting the door and pushing a chair under the doorknob. However the chair doesn't keep hold as the door breaks open, and Sadie (the young black woman) and two other guys rush in to find the bluesman having some kind of seizure. Sadie tries to keep him alive, but the bluesman responds by whispering "black dogs"
Sam's on his laptop and informs Dean that he's officially in the Fed's database. Dean laughs it off, seemingly very happy at the situation. Sam says it's not funny, that it only makes the job harder and that they have to be more careful. However, there's nothing in the database on Sam yet, which is a good thing. Going over their current hunt, Sam tells Dean that architect Sean Boyden plummeted to his death from the roof of his home, a condominium he designed. He called animal control two days earlier, reporting of seeing "vicious, wild black dogs". Authorities couldn't find it and no one else saw it. After that he doesn't show up for work, and two days later, he died. Sam says there are spectral black dogs all over the world. Some say they're animal spirits and others say they're death omens.
Sam and Dean pose as writers for Architectural Digest and talk with Sean's business partner. They find out he lived a charmed life. But the weird thing is that ten years ago, he couldn't design for beans. He worked as a bartender at a place called Lloyds. Then overnight, he became this genius designer, designing some of the most ingenious buildings anyone had ever seen.
The boys stop by animal control to get more information. Dean speaks with a girl named Karley who tells him they've received 19 calls total. She gives them the address of Sylvia Pearlman, who was the most recent person to report of seeing black dogs. Karley also gives Dean her myspace address. Sam finds it amusing that Dean thinks myspace is some kind of porn site.
Sam and Dean speak with the maid and find out that Sylvia disappeared two days ago after reporting of seeing black dogs. She was a surgeon at a very young age, the youngest in the history of the hospital. She got the job ten years ago. Dean notices a picture of Sylvia and her friends at a bar, he flips it over and reads Lloyd's Bar 1996.
Sylvia is pacing around the room shivering and nervous. The manager of the motel knocks at the door saying that she either needs to leave or pay for the night. She grabs cash out of her purse. When she turns around, she sees the demon's face fade in and out. She hands the guy her money and slams the door shut.
Sam and Dean walk up to the bar. Dean notices there are yarrow flowers planted in the middle of a bunch of weeds, used for summoning rituals. They find it odd that ten years ago, two people suddenly became sudden successes where there just happens to be a crossroad. Dean starts digging a hole at the center of the crossroad and finds an old metal box buried inside. They open it up and find a bottle of graveyard dirt, a black cat bone, and other deep hoodoo items, used for summoning demons. Dean recalls that crossroads are where pacts are made and realizes that these people aren't just summoning the demon, but making deals with it. Sam says that these people aren't seeing black dogs, but rather hellhounds (demonic pit bulls).
There's rattling at the door. Sylvia is crouched down behind the bed, covering her ears crying. When the banging stops, Sylvia slowly gets up only to be trampled back to ground as the hellhound shatters through the glass window tearing Sylvia to shreds and we see a streak of blood on the carpet.
1930. Robert Johnson's "Crossroad Blues" song is playing in the background. Robert puts his picture in the box with the other hoodoo items, and buries the box in the center of the crossroad. He turns around to find the demon and responds with a simple "Holy". Robert says that he wants her to make him the best bluesman that ever lived. She grants him his wish with a kiss. By the time he opens up his eyes, she's vanished.
Sam and Dean are discussing this hunt. Dean says that this case is like the Robert Johnson Legend, the whole selling your soul at the crossroads deal. Dean explains that Robert Johnson died chocking on his own blood. He was hallucinating and muttering about "big black dogs". Sam says they need to find out if anymore people made deals with this demon. Dean believes they should just forget about this case because it's their decision to make these deals. Sam still insists that they shouldn't leave these people to die. Despite how Dean feels, he agrees to continue on with the hunt.
Sam and Dean notice a line of pepper outside his door. The door suddenly opens and the boys waste no time and get right to the point about the demonic deal he made ten years ago. Darrow gives them five minutes inside. He explains that the stuff outside his door is goofer dust, used as protection against demons. They don't get much out of him and he doesn't seem to want their help. He brushes them off by saying, "sometimes people make their bed and they have to sit down and lie in it." All he wants to do is buy a little time to finish one last painting. However, he does give them the name of another guy who made a deal with the demon, Evan Hudson.
Working at his desk, Evan hears barking outside. He looks out the window but sees nothing. His wife walks in the room to say goodbye before she leaves for the weekend. He gives her a hug and says he loves her.
Sam and Dean go to Evan's house to try and help him. Thinking the boys are demons, Evan slams the door on them and runs into his study. Sam and Dean break down the door and go into the study. After convincing him that they aren't demons, they ask him what he's asked for. Evan tells them that his wife was dying of cancer and that he begged the demon to save her.
Dean tells Sam to take the goofer dust and keep the hellhounds away from Evan and that he's going to the crossroad to summon the demon. Sam thinks it's a bad idea because of the way Dean's been acting. Sam thinks that Dean believes their dad made one of these demonic deals to save his life and that he should stay with him. Despite what Sam thinks, Dean heads for the crossroads.
Dean puts his picture in the metal box along with the other items and buries the box in the dirt. He turns around to find the red-eyed demon very pleased to see him. She says she knows all about him and the deal that their dad made. Dean requests that they talk in his car. She agrees. Meanwhile at Evan's house, Sam's covering every corner of the room with the goofer dust and makes a big circle of the dust around Evan telling him to stay inside the circle. As they're walking to the Impala, Dean tells the demon that he wants her to release Evan from his contract. She says that's not negotiable, that she can't terminate a binding contract. As she starts to get into the car, she notices a devil's trap underneath the car.
The demon however is willing to bring John back just as he was and Dean would be able to live ten more years as a reunited family. However Dean manages to lure her into another devil's trap and begins to perform an exorcism on her. As Dean starts incanting in Latin, the hellhound has gotten into Evan's study and inching closer and closer to the circle. Dean continues to incant as the hellhound slowly begins to eat away at the goofer dust. Before Dean finishes, the demon agrees to end Evan's contract if he lets her out of the devil's trap. She seals the bond with a kiss. Dean lets her out of the trap and she says that Dean should've taken her up on the deal to bring John back. All of sudden, the demon exorcises itself from the girl's body.
Dean doesn't know how he will live now that he knows the truth about their dad's death. He thinks their dad should've died fighting because that was his legacy, not bargaining with it. Sam reminds Dean of all the people their dad saved and for that matter that number of people they saved because of what their dad taught them, that was their dad's legacy and that they must follow in his footsteps to finish what he started.
"Cross Road Blues" by Robert Johnson
"Downhearted Blues" by Son House
"Key To The Highway" by Little Walter
"Hair Of The Dog" by Nazareth
Dean: "MySpace, what the hell is that? Seriously, is that like, some sort of porn site?"
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