The original comic
- Fair for Its Day: The Chinese Conjurer and Tiger Lily are pretty broad stereotypes by modern standards, but they were fairly progressive for the time by being friends to Rupert instead of Yellow Peril villains. They have also always been drawn in realistic style, without the gross racial caricatures seen in some other contemporary works.
- Narm Charm: Most long-time fans will admit it's rather silly, but a charming sort of silly.
Tropes exclusively in the Nelvana cartoon series
- Ear Worm: Nick Jr.'s version of the intro is pretty catchy.
- Hilarious in Hindsight: "Rupert and the Chalk Drawings" involves Rupert Bear and Gregory Guinea Pig entering a world inhabited by erased chalk drawings. Bear in mind that the episode aired years before ChalkZone came to be.
The 2006 CGI cartoon:
- Tastes Like Diabetes: Not as bad as most examples, but still...