Crossroad Demon

Crossroad Demons are a particular type of demon has immense power, both physical and supernatural. A master manipulator, it loves to play on people's emotions, making them feel extreme guilt and/or fear. Its main purpose is to make bargains with desperate people in exchange for their souls. In order to summon a Crossroad Demon, one must find a crossroads and dig a hole in the dead center, putting in a box with their picture, 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. One is also shown in the body of an adolescent teenage girl making a deal with a 14-year old Bela Talbot, and a man on one occasion, when talking with Sam Winchester. Unlike most demons, it has red eyes, placing it higher in the demonic hierarchy.

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 and kills the demon through the head.

Season Five
In "Abandon All Hope...", the Demon Crowley who is Know as Lilith's right hand demon, Is completing a deal in which he seals it with a male to male kiss. He appears to possess the abilities of a Crossroad Demon. He helps the Winchesters by revealing the devil's location and giving up the Colt. It is lend to believe he is the superior Crossroad Demon being so close to Lilith.

Powers
A master manipulator, it loves to play on people's emotions, making them feel extreme guilt and/or fear. Its main purpose is to make bargains with desperate people in exchange for their souls. They also have the ability to teleport and be summon. It is unknown if they possess the same powers as normal Demons.

Family

 * Lilith (Contract Holder - it can be assumed that Lucifer now holds the contracts)
 * Crowley (Possibly Leader)
 * Crossroads Demons (Kindred)

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)

Trivia

 * Crossroad Demons kiss to seal the contract, so it is led to believe that if the demon is male, a handshake is the proper way to seal the contract.


 * In the episode "Abandon All Hope...", Crowley seemed to have sealed his deal with a kiss, but it is unknown if he only did this to annoy the male customer or if all deals are completed this way.