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Starless made it to the Castle of the Two Sisters, located in the Everfree Forest. He decided to come here first as he believed it was the easiest place to find information about magic since the Canterlot Archives were heavily guarded by Celestia’s royal guards, and he didn’t have any magic to overpower them. When he arrived to the castle to look for books, he found another earth pony.

The earth pony’s name was Black Night. He was a black stallion slightly taller than Starless with a slicked back, gray mane and dark crimson eyes. Like Starless, he wears a black cloak. He had came here to find magic as well, magic that an earth pony could use, as he wanted to overthrow Celestia and Twilight Sparkle. He believed that Celestia had been setting up villains like Nightmare Moon and Discord for Twilight to defeat, that they were staging conflicts to make Twilight look like a hero for their own selfish gain, and Celestia’s actions have been dangerous to Equestria. Black Night once had a special somepony he loved. They had recently gotten married when Discord returned and began causing chaos. Black Night’s wife, Limelight, died during Discord’s short reign of chaos, and when Discord was defeated, she wasn’t revived. When Celestia decided to release Discord again and she and Twilight forgave him after teaming up with Lord Tirek, Black Night was convinced that Twilight Sparkle has to die.

Starless didn’t believe him at first until Black Night asked him why these villains had disappeared for a thousand years and only returned when Twilight began her friendship lessons, and who controls the stars that aided in Nightmare Moon’s escape. Starless remembered being robbed by a unicorn trio and agreed to help Black Night find magic. While they searched the abandoned castle, Black Night noticed Starless’s equal sign cutie mark and Starless told him about his village without magic or cutie marks led by Starlight Glimmer. Black Night wasn’t sure about this, believing that Starlight may want all the magic for herself, but Starless was fully aware of Starlight having a real cutie mark and told him he was looking for a spell to transfer magic from a pony to an object to cover that up.

Starless and Black Night spent the next week looking for magic spells in the castle but could not find anything. They decide to raid the Canterlot archives to find something, but as soon as they leave the castle to head there, Starless’s cutie mark returns to him. Something had happened at Starlight’s village.

Starless and Black Night rush over to Starlight’s village, but by the time they arrived, Twilight Sparkle and her friends had already defeated Starlight, who ran away. Starless was infuriated by this, having lost the only true friend he had left (he didn’t consider Black Night a true friend just yet), and he left the village, wanting Twilight Sparkle dead for ruining what Starlight built and taking her away from him. He and Black Night returned to the Everfree Forest, both vowing to destroy Twilight Sparkle for the misdeeds done to them both.

Over the next few years, Starless and Black Night convince several other earth ponies to join them. They each make a trip to Tartarus where they recite a magical chant and are tested by the power of darkness. Most pass the test and are given dark magical powers, but one pony failed the test and was destroyed. All of them now had dark magic they could perform with their hooves. None were as powerful as Twilight, but if they fought together, they could defeat her. Black Night and his gang spend years planning an attack on Equestria and witness the battle against Queen Chrysalis, Lord Tirek, and Cozy Glow, who they all rooted for as they had defeated Discord and were the first villains who posed an actual threat to Twilight and her friends.

One year after Twilight Sparkle became the ruler of Equestria, Black Night and Starless’s plan to overthrow her begins.