Crossroad Demon

Crossroad Demons are a particular species of demon that make deals with mortals. Their deals have immense beneficiary effects, but ultimately at the cost of the human's soul. Crossroad Demons are master manipulators and love to play with people's emotions, particularly negative emotions such as greed, guilt and fear.

A Crossroad Demon can be summoned by digging a hole in the dead center of a set of crossroads and burying a box containing a picture of the mortal wishing to make the deal, some graveyard dirt, and a bone from a black cat. The demon often featured in the series prefers to possess the bodies of strikingly attractive brunette women who appeal to the men making the deals. Exceptions to this include shown in the body of an adolescent teenage girl making a deal with a 14-year old Bela Talbot, and two are shown as men - one when talking with Sam Winchester and the second as Crowley. Unlike most demons, most Crossroad Demons have red eyes.

Characteristics
These demons are easily identified by their red eyes, which most, if not all of them, possess. They are governed by Hell, from which are primarily used as implements in deal-making. Originally, they served Crowley, a position given by Lilith. From their powers, they're extremely powerful, being able to warp reality.

Season Two
First met in "Crossroad Blues", the Crossroad Demon seen most often in the series appears to Dean Winchester when he tries to save a condemned man's life. It appears as a beautiful young woman (portrayed by Jeannette Sousa), and taunts him with remarks about his father's last moments, and how he too made a deal with a demon. Dean manages to trick the demon into walking into a Devil's Trap, and offers to trade the demon its freedom if it lets the man go. When the demon hesitates, Dean begins an exorcism ritual, causing the demon to yield and break the contract. It kisses Dean to seal the deal, and departs from the woman's body.

The demon returns again in "All Hell Breaks Loose - Part 2", now in possession of a woman (portrayed by Ona Grauer), having been summoned by 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.

Season Three
It makes another appearance in "Bedtime Stories" (now portrayed by Sandra McCoy). 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.

Season Four
In "In the Beginning", Azazel possessed  Samuel Campbell and made a deal with Mary Campbell to resurrect John Winchester. In I Know What You Did Last Summer, in a flashback that took place while Dean was dead, Sam summons another Crossroad Demon seeking to resurrect Dean. The Demon (a male, portrayed by Drew Nelson) refused to make a deal, saying Dean was right where they wanted him, at which point, Sam kills him with Ruby's knife.

Season Five
In "Abandon All Hope...", the Demon Crowley who had been identified as Lilith's right hand demon in the previous 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 by 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 (an attractive brunette woman).

Season Six
In the episode "Weekend at Bobby's" Bobby captures one and kills it for Crowley's real name. Sam was hunting one in the episode "The Man Who Knew Too Much" in a flashback when he was soulless.

Season Seven
In the episode "Season Seven, Time For A Wedding", the crossroad demon Guy is making deals with people, particularly with Becky Rosen. He gives her for free a potion that makes Sam fall head over heels for her. Although he eventually confronted by the Winchesters and Garth. Then Crowley shows up, upset that Guy is cutting the deals short and takes Guy to be made an example of.

Powers
The Crossroad Demon's main power is that it can manipulate reality to make the wishes of the mortals it deals with come true. They also have the ability to teleport, to be summoned and to possess mortal vessels. They also appear to have control over Hellhounds which are shown as their main method of dragging a soul to Hell. It is unknown if they possess the same powers as normal demons.

Season 2

 * "Crossroad Blues"
 * "All Hell Breaks Loose - Part 2"

Season 3

 * "Bedtime Stories"

Season 4

 * "I Know What You Did Last Summer" Briefly - Male Crossroad Demon

Season 5

 * "Abandon All Hope..." Crowley

Season 6

 * "Weekend At Bobby's" Crowley and briefly - Female Crossroad Demon
 * "The Man Who Knew Too Much " Briefly - Male Crossroad Demon

Season 7

 * "Season 7, Time For A Wedding"