During his time as Rupert writer, Alfred Bestall added further characters such as the girl guides Beryl, Pauline and Janet, with Beryl's cat, Dinky. These characters were based on Girl Guides from Bestall's own church who asked him in late 1947 if they could have their own adventure with Rupert. They remain part of the comic series even today.

Stories: Bestall continued to contribute his charming illustrations and imaginative stories during this period, creating classics like “Rupert and the Gremlin,”“Rupert and the Magic Whistle,” and “Rupert and the Glass Mountain.” Stories: Bestall’s first annual introduced readers to new stories, such as “Rupert and the Mare’s Nest,”“Rupert and the Two Moons,” and “Rupert and the Goblins.”

Stories: The 1939 annual included stories such as “Rupert and the Old Umbrella,”“Rupert and the Sea Serpent,” and “Rupert and the Goblin’s Cave.” Rupert Bear Annuals have been a tradition in the UK since 1936. However, Rupert Bear was actually created by the English artist Mary Tourtel and first appeared in the Daily Express 16 years earlier on the 8th November 1920. In our guide we look at the early annuals, the rarest annuals, the most expensive annuals and more. The Daily Express newspaper started publishing Rupert's adventures in 1920 and printed both comic strips and annuals. Larratt, Shannon (22 May 2007). " "Rupert visits Coon Island" (!)". Shannon Larratt is Zentastic . Retrieved 25 January 2011. Stories: Bestall’s final years as the primary illustrator for the annuals saw stories such as “Rupert and the Hazelnut Pie,”“Rupert and the Whirlwind,” and “Rupert and the Sky Ship.”

Rupert's unspectacular introduction was in a single panel, the first of 36 episodes of the story "Little Lost Bear" written and drawn by Tourtel. The 1973 book is one of only 12 printed that year showing the much-loved children's character with a brown face on the cover - making it ultra rare and causing a stir among collectors across the world, ahead of the auction at Dominic Winter auctioneers in South Cerney.Half a million copies of the 1973 white-faced Rupert annual were printed - compared to only 12 brown-faced annuals. In 1935 the mantle of Rupert artist and storyteller was taken over by Alfred Bestall, and the first annual was produced in 1936 The New Adventures of Rupert. Bestall proved to be successful in the field of children’s literature and worked on Rupert stories and artwork into his 90s. Bestall’s work can be seen up until the 1973 Annual. Since then various other artists and writers have continued the series, which still runs to this day – Alex Cubie (1974-1977), John Harold (1978-2007) and Stuart Trotter from 2008.

Stories: This annual marked the return of Rupert after the war, with stories such as “Rupert and the Wooden Horse,”“Rupert and the Mystery of the Iceberg,” and “Rupert and the Sea-Gull’s Feather.” In 1991, Rupert Bear featured in an animated television series with 65 episodes and five seasons (13 per season) produced by Nelvana (Canada), Ellipse (France) and Television South (TVS) for the first season (13 episodes), with Scottish TV taking over control from season 2 when Television South lost its ITV franchise. The show followed the style and tone Bestall established in the Rupert newspaper series, with many of the stories being almost direct adaptations of his or others' panel stories from the Daily Express.He said: "It's a bit like the stamp or coin market where, due to a printing mistake, the withdrawn and rarer mistake is worth far more than the genuine article." Sheridan, Simon (2004). The A-Z of Classic Children's Television: From Alberto Frog to Zebedee. Reynolds & Hearn Ltd. pp.32–35. ISBN 1903111277. Stories: Harrold continued the tradition of enchanting tales, with stories like “Rupert and the Magic Torch,”“Rupert and the Secret Shell,” and “Rupert and the Enchanted Pool.”