The Fiendish Five was a group of villains that appeared in Sly Cooper and the Thievius Raccoonus. They were responsible for the murder of Sly Cooper's father and the theft of the Thievius Raccoonus. They had no unified master plan, rather they each sought their own personal gains. Ten years later, Sly embarked on a mission to defeat them, avenge his father and reclaim the book.
My father fought to protect us, but the gang of villains known as the Fiendish Five overpowered him and ransacked our house until they found... the Thievius Raccoonus.
― Sly Cooper, from the opening cinematic[src]
The Fiendish Five was formed by Clockwerk for the sole purpose of wiping out the Cooper Clan, whom he had envied and hated for thousands of years. When Sly was eight years old, the Fiendish Five attacked the Cooper home, killing Conner Cooper and stealing the Thievius Raccoonus. They split the book into five pieces and retreated back to their own lairs, leaving Sly an orphan. Clockwerk, although aware that Conner had a son, left Sly alive because he believed that he would not be a threat without the book.
After the attack on Sly's home, the Fiendish Five went their separate ways, each one with their own schemes in mind. Raleigh began the legend of the "Welsh Triangle" by creating a storm machine to sink ships around the Isle of Wrath. Muggshot took over Mesa City, slowly driving out the locals and turning the city into his gambling empire. Mz. Ruby withdrew from civilization entirely, preparing an army of voodoo creatures to unleash terror on the world. The Panda King returned to the Kunlun Mountains in China to take out his aggression on his oppressors with an avalanche-based extortion scheme. Clockwerk headed to the Krakarov Volcano in Russia to begin his own plans.
Ten years later, Sly, now partners with Bentley and Murray, began tracking down the Fiendish Five members one by one. In the process, he retrieved the stolen pages of the Thievius Raccoonus. After the rest of his cohorts had been defeated, Clockwerk himself was confronted by Sly. He made several failed attempts to kill Cooper, but in the end, he was defeated as well. With Clockwerk dead and the rest of the members incarcerated, the Fiendish Five ceased to exist.
|Raleigh||Isle of Wrath, Wales||Mallet walrus, Welding walrus, Shuriken walrus, Belly walrus, Squid||Chief machinist||Incarcerated|
|Muggshot||Mesa City, Utah||Doberman pinscher, Bulldog, Pit bull, Jailbird, Dalmatian||Chief enforcer||Incarcerated|
|Mz. Ruby||Haitian jungle||Water rat, Mosquito, Spider, Swamp monster, Ghost rat, Fire turtle, Bomb toting rooster, Beast||Chief mystic||Incarcerated|
|Panda King||Kunlun Mountains, China||Gorilla, Ape, Mandrill, Chimpanzee, Monkey||Demolitions expert||Now a member of the Cooper Gang, currently retired in the Kunlun Mountains of China|
|Clockwerk||Krakarov Volcano, Russia||Fire slugs, Robo-falcons||Founder and leader||Deceased|
Behind the scenes
Mz. Ruby is the only Fiendish Five member to be credited in the Voice Actors section of the first game's credits. It is unknown why the males all went uncredited, but according to, they were all voiced by .