With some experience under their belt, the Sailor Guardians in Sailor Moon were ready to face their next opponents after the Dark Kingdom: the Black Moon Clan.
In the 1990s anime, the Black Moon Clan is composed of those people who rejected Neo-Queen Serenity's power and were exiled to the planet Nemesis. To destroy the 30th century and the White Moon Family, the Black Moon Clan sought to eliminate the past.
Here are the villains of the Black Moon Clan, ranked.
10 Calaveras
In the '90s anime, Calaveras didn't get to do as much as her other Ayakashi Sisters. She didn't even have a single solo mission; Calaveras was constantly paired with Petz like Sailor Venus was with Sailor Jupiter. In the manga, Calaveras had mystical abilities, whereas in the anime, she had a pair of bullwhips collectively called Dark Beaut.
She and Petz were the last two Ayakashi Sisters to be purged of the Black Moon's evil.
9 Berthier
Berthier was the second-youngest Ayakashi Sister. She appeared to be dainty, but she was dangerous, too. She commanded water like Sailor Mercury. Although, her control over it was far more advanced. Berthier was also a good chess player whose ability posed a threat to Ami.
Like with Koan, Berthier was purified by the Legendary Silver Crystal.
8 Kōan
Kōan had the most screen-time of any of the Ayakashi Sisters. She also had the most development, character-wise. She began as a shallow individual who only cared about pleasing Rubeus. In battle, Kōan commanded a blue-tinted fire that Sailor Mars had trouble countering.
It was her second visit to the Hikawa Shrine to find Chibi-Usa that changed Kōan's path. She finally realized that Rubeus didn't care about her, and she was cast out of the Black Moon for failing again. Sailor Mars took pity on her and let Kōan know she had more to live for. Sailor Moon then cleansed the youngest Ayakashi Sister of all evil. It was Kōan who also helped reach Berthier, who went into self-destruct mode later.
7 Petz
As the oldest of the Ayakashi Sisters, Petz was arguably the strongest. She had sway over thunder and lightning. Petz wasn't as superficial as her siblings and she was the most stubborn of the bunch.
When it came to taking revenge on Kōan and Berthier for betraying the Black Moon Clan, Petz was given a wand that enhanced her powers. It made her nearly unstoppable until the Sailor Guardians destroyed it. Petz, seeing the error of her ways, allowed Sailor Moon to heal her.
Near the end of R, Petz is shown to be in love with Saphir.
6 Saphir
In the '90s anime, Saphir was a passive villain. He was nothing like his manga counterpart, who was just as evil-minded as his brother and the other Black Moon members.
Displeased with Wiseman's plan, Saphir stole the key card that powered the Black Moon's Malefic Black Crystal. He escaped to the past, injured, and was taken in by Petz and her reformed sisters. Initially, Petz feared Saphir had come to kill them as punishment for defecting from the Black Moon. This implied that maybe Saphir wasn't always so peaceful.
In hopes of convincing his brother, Prince Dimande, that Wiseman wasn't to be trusted, Saphir met with him under the Sailor Guardians' protection. Unfortunately, the brothers' talk was interrupted by Wiseman.
5 Esmeraude
Green Esmeraude was Rubeus' successor. She was similar to Zoisite; they both wanted their colleagues out of the way so they could be put in charge. However, Esmeraude left Rubeus to die in his exploding UFO rather than directly having him killed.
Esmeraude seems like a worthy villain, but she didn't engage in combat with any of the Sailor Guardians until Wiseman turned her into a dragon. Esmeraude's love for Prince Dimande also clouded her judgment, and she accepted Wiseman's 'help' without thinking he could be up to something.
As formidable as Esmeraude's dragon form was, she was no match for Sailor Moon in the end.
4 Rubeus
Crimson Rubeus was the first general put in charge of finding Chibi-Usa in the past. He also oversaw the Four Ayakashi Sisters. Rubeus was a manipulative man who used his underlings' affection for him to his advantage. When they betrayed him or became disposable, Rubeus acted on his own accord. This meant challenging the Sailor Guardians directly.
Rubeus nearly bested Sailor Moon, too, until Chibi-Usa, of all characters, intervened. Finally, aboard Rubeus' UFO in the middle of space, the red-haired Black Moon member was engulfed in an explosion as the Sailor Guardians and Chibi-Usa safely teleported back to Earth.
3 Prince Dimande
The prince of the Black Moon Clan, Dimande, was not the most active participant. He mainly sat at his throne, letting Wiseman and the others handle everything. That's not to say he wasn't dangerous, though. He had a hypnotic power that put others under his control.
Dimande's obsession with Neo-Queen Serenity put Sailor Moon in harm's way several times. And, because he was so under Wiseman's thumb, Dimande never realized he was being exploited. His younger brother, Saphir, and Sailor Moon both reasoned with him, but it was too late.
2 Black Lady
As a keeper of the Dark Gate, Black Lady was one of the most daunting enemies Sailor Moon ever faced. On top of that, she was the evil form of Chibi-Usa, Sailor Moon's future daughter. Seeing Chibi-Usa become one of Wiseman's minions shook Sailor Moon to her core. She was left feeling like she had failed.
The Sailor Guardians couldn't stop Black Lady, nor was the Legendary Silver Crystal effective against her. That is, until Sailor Moon became her future form, Neo-Queen Serenity. She was then able to turn Black Lady back into regular Chibi-Usa.
1 Wiseman
The Black Moon Clan's puppeteer was one of the Sailor Moon universe's greatest evils, Wiseman. Or, also known as Death Phantom. His mythology was expanded upon in the manga, but, in the 1990s anime, Death Phantom was a shadowy, sinister being who wanted power. The Black Moon was a means to an end.
As Wiseman, Death Phantom acted as a seer for the Black Moon Clan. He insidiously revealed his hand and true colors once most of his peers were removed, either by him or through circumstances he arranged. Of all the major villains Sailor Moon faced, few were as conniving as Wiseman. He was absolutely incapable of redemption.