Pokémon has featured a long list of would-be villains over the years. From the disguised-based antics of Team Rocket to the Ultra Beast obsessed Lusamine to the well-placed nuisance of Team Yell, each antagonist has showcased a new way to cause trouble for our heroes and the world at large. As entertaining as many of these villains were, few of them were truly complex characters. Annie and Oakley, a duo of phantom thief sisters, might have relatively simple motivations, but their characterization is perhaps the most interesting of any Pokémon villain.
The two made their debut in Pokémon Heroes: Latios & Latias. The English and Japanese versions of the movie have some notable differences. In the dub, they're Team Rocket members trying to take over the world, while in the original Japanese, they're just sisters with the more modest aim of taking over the city of Alta Mare. Either way, they're great characters.
Their main goal in the movie is to capture Latios and Latias and steal the Soul Dew to use them as a power source for the Defense Mechanism of Alto Mare ("DMA" for short). The DMA was used to protect the city from outside dangers, but it can also be used as a weapon, even capable of reanimating the evil Kabutops and Aerodactyl, so it's under heavy security at the museum.
While the movie's plot is rather simple, the dynamic between the thieving sisters has surprising complexity. Annie is the older of the two, a girly-girl who uses her good looks to her advantage and cares more about looking pretty than taking over the world. Oakley, the younger sister, is the brains of the two, developing plans to steal the Soul Dew and use the DMA. She's shown to be a quick learner, able to figure out how to use the DMA properly in a matter of minutes.
Despite her intelligence, she didn't know when to stop while she was ahead and became filled with delusions of grandeur. This is most likely a side effect caused by the dark energy that the machine produces, as Latios and the Soul Dew also suffer effects from this same energy. Because the DMA produces this energy while in use, the one controlling the machine is at risk of absorbing that energy. Oakley couldn't handle the amount of energy she was exposed to, thus losing control of herself and becoming obsessed with controlling the world.
Despite their differences, their personalities complement each other. Annie shows how much she cares about her sister when she doesn't run away after Oakley begins losing control. She stays by her sister's side and tries to help her, even getting stuck inside the machine to try getting her out. They wouldn't be rescued until the police came and arrested them. Criminal partners would usually turn on each other by this point, blaming each other for the plan not working, but this isn't the case with Annie and Oakley. Instead of placing blame, they just accept that they failed and face their punishment. Their sisterly bond and sense of responsibility make them one of the most memorable villainous pairs in Pokémon.
