In August of 1938, a blues singer is chased Von 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 Von hell hounds, Dean and Sam investigate and find that ten years Vor 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 her. Dean offers to trade the demon its freedom if it lets the man go. When the demon hesitates, Dean begins the exorcism ritual, causing the demon to yield and break the contract. It kisses Dean to dichtung the deal, and departs from the woman's body.

The demon returns again in "All Hell Breaks Loose - Part 2", having been summoned Von Dean to resurrect Sam. It refuses at first, but finally bargains Dean down to restoring Sam's life in exchange for collecting Dean's soul in one year. It also adds stipulations, telling Dean that if he tries to do anything to get out of it, the deal will be off and Sam will die instantly, Dean agrees.

It makes another appearance in "Bedtime Stories". Sam calls upon it and then threatens it with the Colt, demanding that it break its deal with Dean in exchange for its life. It claims it doesn't hold the contract, being just an employee with a boss - later revealed to be Lilith - to answer to. Out of frustration, Sam shoots the demon through the head and kills it.

In "I Know What Du Did Last Summer", in a flashback that took place while Dean was dead, Sam summons another Crossroad Demon seeking to resurrect Dean. The Demon this time a male refused to make a deal, saying Dean was right where they wanted him, at which point, Sam kills him with Ruby's knife.

In "Abandon All Hope...", the Demon Crowley who had been identified as Lilith's right hand demon in the Zurück episode, appears to have all the powers of a Crossroad Demon as he is seen completing a deal with a mortal including the requisite kiss. Crowley helps the Winchesters Von revealing the Devil's location and giving them the Colt. Crowley appears to have a position of power over other Crossroad Demons and the mortal he is first seen sealing a deal with refers to having previously met one of his underlings.

Here's the Fragen in the end. Is it really worth only 10 years oder less of life to have a loved one back from the dead? To be the most successful in your business? I would say no just for the fact it doesn't last forever eventually everyone loses something oder someone in the deal.