Bestall proved to be successful in the field of children's literature and worked on Rupert stories and artwork into his nineties.

Rupert Bear is a part of children's culture in the United Kingdom, and appears in 4 TV shows based on the character.

Aside from his best friend Bill Badger, some of the most enduring pals are an elephant (Edward Trunk), a mouse (Willie), Pong-Ping the Pekingese, Algy Pug (who actually pre-dates Rupert),[4] Podgy Pig, Bingo the Brainy Pup, the identical twins Freddy and Ferdy Fox, the identical twins Reggie and Rex Rabbit, and Ming the dragon.

[5] There are also a few human characters in the stories, such as the Professor (who lives in a castle with his servant, Bodkin), Tiger Lily (a Chinese girl), her father "the Conjuror," and several less frequently occurring characters such as Sailor Sam, Gaffer Jarge, Captain Binnacle, the Sage of Um (who is seen travelling in a magical upside down umbrella) and Rollo, the Gypsy boy.

Each story begins in Nutwood, where Rupert usually sets out on a small errand for his mother or to visit a friend, which then develops into an adventure to an exotic place such as King Frost's Castle, the Kingdom of the Birds, underground, or to the bottom of the sea.

At the end of the story Rupert returns to Nutwood, where all is safe and well, and where his parents seem perfectly sanguine about his adventures.

Bestall developed the classic Rupert story format: the story is told in picture form (generally two panels each day in the newspaper and four panels to a page in the annuals), in simple page-headers, in rhyming two-line-per-image verse, and as running prose at the foot.

Rupert's unspectacular introduction was in a single panel, the first of 36 episodes of the story "Little Lost Bear" written by Herbert and drawn by Mary Tourtel.

Bestall drew the Rupert stories for the Daily Express until 1965; and continued to illustrate the covers for the annuals until his retirement in 1973.

[11] The characters were all puppets, although the opening sequence featured a toy Rupert bear sitting in a live-action child's bedroom.

Rupert's friends and flying chariot appeared straight from the Daily Express pages, although he was joined by some new friends including Willy Wisp, Drizzle, Della, Jimmy, Mr Grimnasty, Gypsy Granny, Chun-Mao, The Wise Old Wizard, and Mr Koskora The theme song, written by Len Beadle (also known as Frank Weston) and Ron Roker, sung by Jackie Lee, reached number 14 in the UK charts in 1971.

[citation needed] The show has been returned in the United Kingdom on the satellite and cable network Tiny Pop.

Changes to the characters are that Rupert wears trainers and his fur has a slight tan; Bill wears a dark blue leather jacket and blue pants with yellow stripes instead of his suit and bowtie, and tends to carry a personal digital assistant with him at all times; Pong Ping has become a girl who uses magic and had her name reversed; Raggety, who rarely appeared before, has become a friendly tree elf; Ming a baby dragon and Ping Pong's pet; Edward no longer has tusks, his trunk has been straightened and he wears an orange T-shirt and brown shorts; and one of the fox twins (Ferdie) has been changed into a girl named Freda.

[citation needed] A short film directed by Geoff Dunbar based on ideas/music/songs by Paul McCartney was made in 1984, titled Rupert and the Frog Song.

The film contains a song titled "We All Stand Together", written by McCartney and arranged by the Beatles' producer George Martin.

[citation needed] In September 2020, Royal Mail issued a set of eight stamps to commemorate the centenary of Rupert Bear.

[19] A cartoon of Rupert superimposed on a Robert Crumb drawing, showing the bear in a sexual situation, was a notable part of the notorious edition of the British underground magazine Oz guest-edited by schoolkids.