Crossroad Demon

Crossroad Demons are a unique kind of demon that grant any wish at the price of someone's soul.

Characteristics
These demons in particular have red eyes. They are Hell's deal-making demons. Currently, they are governed by Crowley, who is the King of Hell and, in turn, the head of the Crossroads. Originally, they served Crowley, as he was King of the Crossroads, as well as the most powerful Crossroads demon.

While the deals are typically beneficial to humans, the benefits are almost always temporary as the deals are usually made at the price of the person'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 most 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 the one shown in the body of an adolescent teenage girl making a deal with a 14-year old Bela Talbot and three shown as men - the most significant of which is Crowley.

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.

Another Crossroads Demon makes an appearance in a flashback in Time Is On My Side in which a Crossroads Demon, possessing a little girl, makes a deal with a young Bela Talbot, promising to kill her abusive parents in exchange for Bela's soul in ten years.

Season Four
In I Know What You Did Last Summer, in a flashback that took place while Dean was in Hell, Sam summons another Crossroad Demon, wanting to trade places in Hell with 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). In The Devil You Know and Two Minutes to Midnight, Crowley, referring to himself as the King of the Crossroads, makes a deal with Bobby Singer to use his soul to find Death. He keeps the soul to have leverage over Sam and Dean, though he promises to return it once the Apocalypse is over. Crowley also takes it upon himself to use the deal to restore Bobby's legs, saying he wasted his deal with him.

Season Six
In the episode Weekend at Bobby's Bobby captures one and tortures it for Crowley's real name by scorching its bones. The demon eventually breaks and gives it up, but Bobby burns her bones instead of exorcising her, killing her. Sam may have been hunting one in the episode The Man Who Knew Too Much, as shown in a flashback to when he was soulless.

Season Seven
In the episode Season Seven, Time For A Wedding, the crossroad demon Guy is making deals with people and attempts to make one with Becky Rosen. He gives her a potion for free that makes Sam fall in love with her. He is eventually confronted by the Winchesters and Garth. Then Crowley shows up, upset that Guy is cutting the deals short (which would hurt their credibility). He cancels all the deals Guy has made and then takes takes Guy to be made an example of.

Season Eight
It's revealed that in 2003, Crowley himself made deals with three people after being summoned by one. In the present, he sends a Hellhound to collect on the deals, but only gets two of them before the Hellhound is killed by Sam.

In Taxi Driver, in order to find a way to sneak into Hell, Sam and Dean summon a Crossroads Demon, painting a giant Devil's Trap in the middle of the crossroads so he is trapped the moment he arrives. Sam and Dean torture the demon for information with holy water at a warehouse and he refuses at first as he fears what Crowley will do to him if he finds out. The demon finally breaks and reveals that rogue Reapers sneak mortals and souls between Earth, Heaven and Hell for a price. The demon then begs them to kill him, saying he's better off dead than with Crowley. Sam and Dean agree, but first have him tell them where to find one of the rogue Reapers.

Season Nine
In Devil May Care, a Crossroad Demon possessing an old woman to make deals with kids and four other demons convened with Abaddon. The demon was skeptical of Abaddon's plans to take over Hell and repeatedly asked where Crowley was. Fed up with the demon, Abaddon used her powers to exorcise her, telling her to warn all of the demons in Hell that she is coming.

Powers & Abilities
As Demons, they possess similar powers to normal demons. It is unknown if they possess all the same powers as normal demons though. Although normally weaker demons (considering themselves "Salesmen" rather than fighters) they can be incredibly powerful, as evidenced by Crowley. They also appear to have control over Hellhounds which are shown as their main method of dragging a soul to Hell, although this not so much a power, as many types of demon have shown control over hellhounds.
 * Possession - Standard demon power.
 * Super Strength - Standard demon power.
 * Reality Warping - 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 can't however do this without a deal for a soul. Crowley reveals that their ability is purely down to a spellcasting, rather than innate power. Although never specified, there are limits to what they are capable of.
 * Teleportation - They have the ability to teleport, and commonly appear when summoned to make deals.
 * Immortality - As demons they have the potential to live forever, some have been known to make deals for decades.
 * Invunerability - Standard demon power, still vulnerable to demonic weaknesses though.

Season 2

 * Crossroad Blues
 * All Hell Breaks Loose - Part 2

Season 3

 * Bedtime Stories
 * Time Is On My Side

Season 4

 * I Know What You Did Last Summer  - male crossroad demon

Season 5

 * Abandon All Hope... - Crowley
 * The Devil You Know - Crowley
 * Two Minutes to Midnight - Crowley

Season 6

 * Weekend At Bobby's - Crowley and female crossroad demon
 * Family Matters - Crowley
 * All Dogs Go To Heaven - Crowley
 * Caged Heat - Crowley
 * Mommy Dearest - Crowley
 * The Man Who Would Be King - Crowley
 * Let It Bleed - Crowley
 * The Man Who Knew Too Much - Male crossroad demon

Season 7

 *  Meet The New Boss   - Crowley
 *  Slash Fictio n - Crowley
 * Season 7, Time For A Wedding - Guy
 * There Will Be Blood - Crowley
 * Survival of the Fittest - Crowley

Season 8

 * We Need To Talk About Kevin - Crowley
 * What's Up, Tiger Mommy? - Crowley
 * A Little Slice of Kevin - Crowley
 * Goodbye Stranger - Crowley
 * Taxi Driver - Unnamed male demon and Crowley
 * Pac-Man Fever - Crowley
 * The Great Escapist - Crowley
 * Clip Show - Crowley
 * Sacrifice - Crowley

Season 9
Kreuzungsdämon
 * Devil May Care - Crossroad Demon and Crowley