Crossroad Demon

Crossroad Demons are demons tasked with "buying" souls for Hell through deals with humans. These deals consist of the demon granting the human's wish in exchange for ownership over that person's soul, resulting in the person dying and going to Hell to be transformed into a demon upon death. Crossroad demons are named as such because they in particular can be summoned at crossroads by humans seeking to make deals.

Characteristics

These demons tend to have red eyes. Named as they create their pacts at a crossroads, they are Hell's deal-making demons. They answer to the King of the Crossroads; previously, this was Crowley. The identity of their current King since Crowley became King of Hell is not disclosed, though Crowley still has authority over them so it's possible he still holds this position to some extent.

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. All Crossroads Demons sign their contracts with a kiss.

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. While their true form is black smoke like other demons, Crowley's was red.

Season Two

Dean's Crossroad Demon first makes an appearance in Crossroad Blues where it makes a deal with Robert Johnson and several other people including George Darrow and Evan Hudson who uses the deal to save his wife from cancer. In order to save Evan, Dean decides to summon the demon and exorcise it which will buy time as it will take the demon time to get out of Hell. However, when he does summon it, he attempts to get it to break Evan's deal instead, trying to lure it into a devil's trap. The demon avoids the trap and taunts Dean about his father being trapped in Hell, offering him a ten-year deal to save him. Dean pretends to agree, but then successfully lures the demon into another devil's trap. Dean offers the demon a deal of his own: break the deal and he will set her free, refuse and he'll exorcise her. The demon refuses so Dean starts an exorcism. Finally, partway through the exorcism, the demon gives in and breaks the deal. Dean breaks the devil's trap and frees the demon who after taunting him one last time, flees the woman it was possessing, leaving her confused.

The demon returns again in All Hell Breaks Loose - Part 2, now possessing another woman, 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, in a different host. 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 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 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. He is later able to use the information to force Crowley, who is now King of Hell, to break his deal. 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. After the Winchesters, Garth and Becky defeat Guy, 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.

In Blade Runners, trying to find Crowley Sam and Dean summon a Crossroad Demon into a devil's trap only to find her possessing Snooki which they comment makes sense. Pointing out that if Abaddon takes over she'll be out of the job, Sam and Dean get Snooki to tell them what she knows of Crowley's whereabouts before exorcising her to her annoyance.

Powers & Abilities

As demons, they possess all standard demon powers. Though salesmen, they're physically stronger and more powerful than black-eyed demons, being a higher rank. They also appear to have control over individual hellhounds (their main method of dragging a soul to Hell), although other demons (e.g. Meg) can also control hellhounds. Crossroads demons cannot control other demons' hounds.

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 (though he may be lying) . 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.

Trivia

While deals are primarily made by Crossroad demons, high-ranking demons such as Azazel and Lilith also have the authority to create and hold contracts.