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"Two roads diverged in a yellow wood..."—Robert Frost, The Road Not Taken
Just like bridges, crossroads often feature as the setting for portentous happenings - there's something symbolic about the (often ancient) intersection of two paths that gets people's imaginations going. Often they are used to represent the intersection between two worlds.
Crossroads also tend to represent places where a character can make a life changing decision, especially if there is conflict over which path to take.
- The Incredible Hulk was banished to "The Crossroads" by Doctor Strange when he was "mindless" to (A) get him away from Earth and (B) let him choose where he wanted to live. But he never found a place he liked and eventually he was brought back to Earth.
- Hellboy: In Wake the Devil, Hellboy is tied up and left at the crossroads as an offering for the vampire Guirescu; he meets Hecate there immediately afterwards. In "The Body", Hellboy waits at a crossroads to meet a trio of The Fair Folk.
- This is where the brothers meet Big Dan Teague in O Brother, Where Art Thou?? as well as well as Tommy after he made a Deal with the Devil.
- Near the end of Cast Away, the intersection is symbolic.
- The 1986 Ralph Macchio movie Crossroads mirrors the Robert Johnson legend, and hinges on this trope.
- It is in a crossroad that not only Buster and Fred meet in The Fearless Four, but also where the arrows indicating the direction to Paris and Bremen are switched, driving thus the plot of the story.
- The Angel of Death in Hellboy II takes this a step further: "I am his death, and I will meet him at every crossroads."
- In Supernatural, deals with "crossroads demons", the ones that actually make deals that both parties are bound to, have to be made at crossroads. Those demons can be summoned with some personal affects and a bag of crossroads dirt, though. There's not much else to say here that isn't covered by Deal with the Devil and Be Careful What You Wish For.
- There was a long-running British Soap Opera called Crossroads. Given that significant events are always happening to soap characters, the title may not have been coincidental.
- In Burn Notice Michael is often told that he's At the Crossroads or at a fork in the road by people who want him to make a choice.
- The Doctor Who episode "Turn Left" features Donna making a literal At the Crossroads decision near the beginning of the episode, and again near the end. The choice she makes affects the entire universe.
- Charles de Lint has a character based on the legend of the guitarist at the crossroads.
- Tamora Pierce's series of books set in the Tortall universe has the big gods, like Mithros (war and justice), and the Goddess (fertility, women, agriculture), but it also has minor gods like Weiryn (god of the hunt for a small mountainous area), and rather hilariously a god of crossroads, NOT a god of travelers, just a god of ACTUAL crossroads.
- Alan Gordon's medieval mystery An Antic Disposition (a retelling of the Ur-Hamlet) begins with two people meeting by chance at a crossroads. The narration says, "A crossroads, properly designed, reminds you that you are making a choice."
- Technically, in Harry Potter, King's Cross Station takes on this significance -- you can't deny it's where many ways meet, and it's the go-to exchange point between the magical and Muggle worlds (in this respect, The Leaky Cauldron fulfills a similar purpose for Diagon Alley.) But King's Cross' symbolism really comes into play in book seven, when it's where Harry has his brief sojourn at the crossroads with the afterlife.
- Happens rather a lot in Tales of the Five Hundred Kingdoms, naturally enough as there's a force in this world that tries to make things happen the way they do in fairy tales, we see several secret tests of character at a crossroads from the POV of both the testee and the tester.
- Many folk songs, eg. The Devil Went Down To Georgia, and Widdecomb Fair.
- Robert Johnson's "Cross Road Blues," while ostensibly about a failed attempt to hitch a ride, is often linked to the legend that Johnson made a Deal with the Devil for the ability to play music (a legend more supported by his "Me and the Devil Blues"). This confusion of the legend with Johnson's best song informs the brothers' meeting with Tommy (a clear Expy of Johnson) in O Brother, Where Art Thou?. Also, the song itself is best known from the cover by Cream.
- Driving South by The Stone Roses on their album Second Coming makes reference to both the crossroads and Johnson's song.
- The Well of the Saints, a play by Irish writer J M Synge about a blind man who is cured, partially takes place at a crossroads to represent the boundary between reality and the supernatural and between blindness and sight.
- Oedipus Rex has an encounter at a crossroads that ends violently and then a bunch of other stuff happens.
- "The Crossroads of Destiny" is the name of the season 2 finale of Avatar: The Last Airbender. Although it's not a literal example of this trope as there are no actual crossroads, both Zuko and Aang are forced to make very tough decisions in this episodes and they don't make the decisions you'd necessarily expect. It's also one of very few episodes in the series not named after something literal (like The Swamp and The Southern Air Temple), but rather something figurative. The name is even quoted by The Obi-Wan at one point. On a side note, it was one of the greatest episodes in the series.
- In an episode of Metalocalypse, the band members are urged by one Mashed Potato Johnson (an obvious reference to the Robert Johnson legend) to sell their souls to the Devil in exchange for the ability to play blues music. They go to a crossroads to do so, and Hilarity Ensues when their negotiations result in the contract being significantly in their favor.
- In Tales of Monkey Island, pirates go to the Crossroads when they die. There's also some nice symbolism at the end when Guybrush uses a spell to get back to the land of the living.
- There is a crossroads in front of Castle Oblivion in Kingdom Hearts Chain of Memories. Inside, Sora choses to forget everything from Castle Oblivion, including his new friend Namine, in order to regain his older memories.
- At the end of Reverse/Revith, Riku's decision on the crossroads is different. He chooses to follow neither the road to light nor the road to darkness, but rather the road to dawn.
- Dominic Deegan's sight (not his second-sight, his mundane sight) goes all grey when someone close to him is about to encounter a metaphorical crossroad.
- SCP Foundation-023, based on the mythological black shuck, can only be contained in crossroads and other intersections, such as the intersection of two corridors.
- The Older Than Feudalism Ur-example and Trope Maker is probably the goddess Hecate of Greek Mythology who was goddess of the crossroads as well as her prominent realms of the dead, ghosts, magic, night and moonlight (if you didn't live in a region big on Artemis or Selene). Like other deities of paths such as Hermes or the Roman Janus, her offerings would be placed at the crossroads so she would control the evil spirits that walked along them. The Romans had a comparable deity Trivia (though one a bit Darker and Edgier) so this aspect continued strongest. This rite survived for quite a while into the Christianisation of Europe which leads to religious figures specifically demonising the practice which leads to the strong Deal with the Devil associations throughout Western Civilisation.
- Voodoo in particular has a fascination with the crossroads as symbolism. Papa Legba is the lwa of the crossroads that serve as the boundary between the living and the dead. Kalfou, his evil side is also associated with them.
- There are old legends that vampires and other supernatural creatures must be buried at a crossroads.
- Also, folklore tells us vampires get disoriented (or even driven mad) at crossroads, and cannot tell one direction for another. Urban vampires seem to have developed a strong resistance to this weakness, especially those that frequent downtown districts.
- There was an old German folk belief that a man can turn into a werewolf if he goes at a full moon's night to a crossroad, wearing nothing but a belt made of a wolf's pelt. At midnight, the transformation will happen.
- According to legend, Robert Johnson sold his soul to the devil for the ability to play guitar at a Crossroads. Many other uses of crossroads (like on Supernatural) are based on this legend.
- Criminals were sometimes executed at crossroads, then buried there. Likewise, people who committed suicide and were therefore unqualified to enter Heaven were buried at a crossroads when available. Certainly those suspected of being vampires (also unqualified) were. And until the 1800s, so were actors.
- The rationale for this was that the unquiet spirit would not know which of the roads to follow in order to seek vengeance on the living.
- Note that in the ages before exact maps, standardized road signage, Google Earth and GPS systems, crossroads indeed had an inherent danger: Take the wrong road, and you end up hundreds of miles away from where you wanted to go. (Of course, in some cases this may have lead to a better life for the people involved.) Still not surprising that people started to associate crossroads with fear.
And that has made all the difference.