As surprising as it sounds, even this kid-friendly adaptation of a kid-friendly comic strip had its share of disturbing and creepy moments.
- "Rupert and Little Yum" starts with Rupert taking a shortcut through, last he knew, the grounds of an empty mansion, only to find himself grabbed by a thuggish-looking employee. The guy takes him inside where the new owner warns him to tell all the kids to stay off his property or else. Rupert's staring at the guns mounted on the wall as he says, "Yes, sir." The whole time the owner's threatening this little kid, the thug grabs him every time he moves. Unlike the fantastic threats the hero usually faces, the whole thing is too well grounded in reality not to make you cringe.
- Those voiceless, eyeless, multi-armed "Black Turbans" in "Rupert and the Lamp."
- "Rupert and the Mulp Gulper" deals with a race of hedgehog-like people called Mulps being repeatedly terrorized by the titular Mulp Gulper and sending a champion to deal with the monster only for the poor sap to meet their doom. As if the episode opening with the Mulps' last champion being eaten alive by the Mulp Gulper isn't startling enough, Rupert's friend Algy nearly suffers the same fate.
- "Rupert and the Missing Snow" ends with Rupert, his uncle Polar, and Will all almost getting accidentally Swallowed Whole by a Monster Whale suffering from a terrible toothache for mistaking the North Pole for candy. They fortunately escape though Polar remarks it was very nearly unfortunate. They could've ended up digested, or trapped forever inside the belly of a friendly but unaware giant whale.
- "Rupert and A.R.C.H.I.E." has some rather disturbing fun with the trope A.I. Is a Crapshoot by having the Professor's robot A.R.C.H.I.E. destroy his own control while in wood-chopping mode and starts going about chopping at everything he sees with his axe, Rupert and his friend Bill Badger just barely avoiding the robot's axe swings. Things later get worse when A.R.C.H.I.E. cuts down a pole carrying a power line and gets electrocuted, which causes his eyes to glare and glow red before he goes about making more of himself to continue hacking at stuff to make firewood.
- The pickle monster from Podgy Pig's nightmare in "Rupert in Dreamland" is pretty scary-looking what with its menacing eyes and grin full of fangs. It's also frequently implied that it wants to eat Podgy.
- Perhaps it's from having the perfect balance of realism and supernatural powers, but the Great Mephisto can easily come across as the show's creepiest villain. He doesn't use his powers for anything flashy or extreme like enslaving a kingdom. He just uses them to brainwash children. In the climax, the boys run from him in sheer terror you've never seen them show against any of their enemies before. The scene where he tries to hypnotize Rupert the second time, as the boy desperately moans, "No...", knowing what's happening but powerless to stop him, is all levels of disturbing.
