The title character of the show. A young anthropomorphic bear who is very well-mannered, has a lot of friends, and often goes on adventures.
- All-Loving Hero: He gets along well with just about everyone and everything.
- Badass Adorable: He's a young bear boy who's gone through a lot of adventures and has gone toe to toe with plenty of villains.
- Guile Hero: He frequently saves the day by using his wits.
- Iconic Outfit: His red shirt combined with his plaid yellow scarf and pants make a most memorable ensemble.
- Intergenerational Friendship: Rupert is a child and quite a few of his closest friends are adults, the most notable ones including the Professor, Constable Growler, and the Wise Old Goat.
- Nice Guy: He's very cordial and kindhearted to everyone in Nutwood
- Species Surname: He's a bear whose last name is Bear.
Mr. and Mrs. Bear
Rupert's parents, who are very loving towards their son.
- Childhood Friend Romance: Hinted at in "Rupert and the Mulp Gulper", where Mr. Bear reminisces on testing his abilities at carnival games to impress his girlfriend when he was younger and Mrs. Bear replying with a statement that strongly implies that she was the girlfriend Mr. Bear was referring to before the two smile and cuddle.
- Good Parents: It is quite clear that they love and care about their son and that they couldn't be prouder of his selflessness and kind ways.
- Happily Married: As with most parents seen in children's cartoons, they are clearly happy together.
- Strong Family Resemblance: Both of them look a lot like their son. In "Rupert in Timeland", Rupert even mistakes his own reflection for his father when he's time-warped to a future where he is an adult.
- Unnamed Parent: Neither of their first names are revealed.
Rupert's best friend.
- Alliterative Name: His first name and his last name both begin with B.
- Dreadful Musician: He has a terrible singing voice.
- Hair-Trigger Temper
- Lovable Coward
- Species Surname: He's a badger with the surname Badger.
Another of Rupert's friends.
- Alliterative Name: His first name and his surname both begin with P.
- Big Eater: Podgy really loves to eat.
- Gluttonous Pig: Like most anthropomorphic pigs in fiction, Podgy is obsessed with food.
- Innocently Insensitive: He often doesn't intend to be mean to people.
- Jerk with a Heart of Gold: The "jerk" part is downplayed due to Podgy being an overall Nice Guy, but he can be selfish and mean at times.
- Meaningful Name: "Podgy" means stocky or overweight.
- The Millstone: Due to his tendency to think with his stomach and not consider consequences, he regularly gets himself and Rupert into trouble.
- Species Surname: He's a pig with Pig as his last name.
- Digging to China: He has an elevator that takes it's occupants to China.