In 1996, wanting artistic talent, George Darrow used hoodo to summon a Crossroad Demon to make a deal. George got the talent he wanted, though he never became famous as he didn't ask for that. Unexpectedly, the demon remained at Lloyd's Bar for a week and made deals with Sean Boyden, Silvia Perlman and Evan Hudson to become a great architect, a famous doctor and to cure his wife's cancer respectively.
Ten years after making the deals, the demon returned to collect on them, sending a hellhound to kill Sean Boyden. Trying to avoid it, Sean ended up falling off the roof of his condo, but not before he reported seeing a black dog which drew the attention of Sam and Dean Winchester who were unaware of what truly happened to him and thought they were dealing with a Black Dog. While investigating, they learn from Sean's business partner that ten years before, he had no talent and then suddenly got an incredible talent overnight before which he worked as a bartender at Lloyd's Bar.
Looking for clues, Sam and Dean follow up on a call to Animal Control by Doctor Pearlman about a black dog and find out that she too had gotten sudden talent overnight ten years before and she had a connection to Lloyd's Bar. Shortly afterwards, Doctor Pearlman is attacked and killed by the hellhound as it comes to collect on her deal.
Visiting Lloyd's Bar looking for clues, Sam and Dean notice yarrow flowers which are used in summoning rituals and that its located at a crossroads. Remembering that crossroads are where demon deals are made, Dean digs in the middle of the crossroads and finds George Darrow's summoning box still there. Sam and Dean realize that people were making deals with a demon and that its actually a hellhound after them to collect on their deals. Sam becomes determined to save anyone still left alive who had made a deal and convinces a reluctant Dean to help him. The two then visit Lloyd's to find out who George is and where they can find him using his picture from the summoning box, figuring he's their best lead as he summoned the demon.
Finding George's apartment, they find that he has spread goofer dust in front of the door to protect himself and convince him to talk to them. George gives them some goofer dust and tells them that he doesn't care if he dies since he summoned the demon in the first place and is responsible for the deaths of the other people who made deals as a result. George tells them the name of the last person to make a deal, Evan Hudson, but refuses their help to break his deal as he wants to die for what he did. George tells them that he just plans to hold off the hellhound long enough to finish his last painting before sending them on their way.
In the meantime, Evan notices the barking of the hellhound and sends his wife away to see her sister as he knows what's coming for him. Shortly after his wife Julie leaves, Sam and Dean arrive and Evan flees them, scared, when they mention Lloyd's ten years before. After cornering him, the Winchesters reveal that they know about his deal to Dean's disgust. Evan tells them he made the deal to save his wife's life since she was dying of cancer. Needing a way to stop the demon and save Evan, Dean tells Sam to stay behind and use George's goofer dust while he goes to the crossroads and summons the demon. Dean explains that he can trap and exorcise the demon which will buy them time to find something more permanent as it will take the demon time to return from Hell. While Sam protests since they both realize their father likely made a similar deal to save Dean's life, Dean goes anyway once Evan hears the hellhound returning. While Dean is gone, Sam spreads goofer dust around the room and in a circle around Evan, but the hellhound eventually breaks through their defenses and they end up trapped in a closet.
At the crossroads, Dean uses George's summoning box to summon the Crossroad Demon who appears in the form of a young woman. After the demon displays knowledge of him, Dean tells her that he wants to make a deal and leads her to the Impala which he has painted a devil's trap under. During the walk, Dean offers himself up in exchange for the demon breaking Evan's contract, causing the demon to comment "like father, like son" and tells Dean how his father had made a deal to save him. However, the demon notices Dean's devil's trap before she can enter the car and is pissed at Dean's stunt. Backing Dean towards a nearby water tower, the demon tells him she won't kill Dean because she enjoys his suffering at the thought of his father sacrificing himself for him and that she could've made a deal with him to bring John back. When Dean stops her to ask what she means, the demon offers him a ten-year deal to bring John back. As Dean questions the terms of the deal, he lures the demon beneath the water tower where he has placed another devil's trap and succeeds in trapping her this time. The demon demands Dean let her go, but Dean offers her a deal instead: call off her hellhounds and release Evan from his contract and he'll let her go, otherwise he'll exorcise her. The demon refuses so Dean starts an exorcism from his father's journal. As the exorcism nears its end, the demon gives in and breaks Evan's deal with a kiss to Dean, signifying the completion of their own deal. The deal is broken just in time to save Sam and Evan. Afterwards, the demon informs Dean that she broke Evan's deal and that he and his wife will live long lives. While Dean contemplates finishing his exorcism, he ultimately keeps up his end of the deal and breaks the devil's trap, freeing the demon. The demon takes the opportunity to taunt Dean about his father being tortured in Hell before she flees her vessel, leaving behind a confused girl
Afterwards, Dean is disturbed by what the Crossroad Demon told him about his father's fate as his father had spent his life chasing Azazel and then made a deal with him instead of killing him to save Dean who doesn't believe it was worth it. Sam questions whether or not Dean had considered actually taking the deal to save their father and while he doesn't respond, he clearly did.
- This skirmish is the first time Sam or Dean use a devil's trap against a demon since Bobby Singer introduced the concept to them. Following their first use here, it becomes a common method of dealing with demons for them.
- One of only four times Dean performs an exorcism on the series though he doesn't complete it here.
- While in this episode Dean uses trickery to lure the Crossroad Demon into a devil's trap, when he and Sam summon Crossroad Demons in Taxi Driver and Blade Runners, they simply paint the crossroads with a devil's trap so the demon is captured immediately upon arrival. In the latter episode, after getting what they want from the demon, Sam starts an exorcism to her annoyance like Dean did here. That time, Sam presumably completes the exorcism though its not shown.