Rupert the Bear – one of my favourite literary characters

As a young girl I liked to read a series of books. Strangely, as an adult, I have steered away from book series, preferring to read stand alone books like Jane Eyre and Great Expectations.

I have noticed that both my boys loved to read a series of book when they were in the prep school. Greg seems to have outgrown this now and reads a lot more stand alone books but Michael is busy reading his way through all the Secret Seven books by Enid Blyton. I think that children find a series comforting with its familiar characters. Young children definitely like repetition and while the requests to read books over and over again, until you could recite them backwards, does eventually stop, the concept of a book series stays around for much longer.

Rupert the Bear is a very memorable book series for me. I loved them as a child and I have a vintage collection of these books as an adult. I have read them many times to both my boys and I still enjoy them.

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Rupert the Bear

The Rupert the Bear books are written along the lines of a comic strip but there is a lot more sophistication in the writing, illustrations and story lines than in a standard comic.

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Rupert is a great character and he is polite and helpful which are characteristics that are worthy of promotion to children. He has lots of interesting friends, most of which are animals that are given the bodies and characteristics of humans. An exaggerated form of personification. All of the animals are drawn to the same scale, regardless of whether the animal is an elephant, fox or a bear. My personal favourites of Rupert’s friends are Podgy Pig and Bill Badger. A couple of humans feature in the books such as the Professor and Tiger Lily. There is also a Merboy, who lives in the ocean, who reappears frequently in the books.

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Rupert lives in a lovely English village called Nutwood and he is always getting involved in exciting adventures that take him to interesting places under the ocean and in magical countries. Rupert and his friends are also subject to mysterious weather conditions and other strange happenings.

According to Wikipedia, there are 82 Rupert the Bear annuals. I don’t have anywhere near that many so I have some shopping to do.

Did you know:

Rupert Bear started life as a daily comic strip in the newspaper in order to compete with the Daily Mail’s Teddy Tail ( first published in 1919 ) and the Daily Mirror’s Pip Squeak and Wilfred, Britain’s first ever comic strip introduced in 1915.

Rupert Bear has stood the test of time, having been seen in the Daily Express every day for over 90 years and having his own Rupert Annuals published since 1936.


Robbie and Michael Cheadle are the co-authors of the Sir Chocolate Book series and Robbie Cheadle is the author of Silly Willy goes to Cape Town


59 thoughts on “Rupert the Bear – one of my favourite literary characters

  1. My granddaughter just turned one, is walking, has said a few words, and is intently interested in the world around her. It won’t be long before she’s ready to enjoy some of the adventures of Silly Willy, and Sir Chocolate. I hope all is going well. Take care.

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  2. I well recall my four birthday – 1960 – and waiting for the promised Rupert Annual which came out to coincide with Christmas shopping. In the middle it had a picture that you just had to brush with a damp paint brush and you got a coloured pciture. I thought this magic! Oh the sophistication!!

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  3. I love Rupert the bear! What a wonderful character! I grew up with a lot of him, winnie the Pooh and Amelia Bedilia. Let’s hope that Rupert is always left as he is and no one decides to dig him back up, like that monstrosity of a Peter Rabbit movie coming out…

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  4. A great book review, Robbie. I remember my teaching days, especially teaching K-3, also remember when my daughter was before 3rd grade. They do like series of familiar characters – that’s their imaginary world of friends.

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  5. Thanks for introducing me to Rupert, Robbie! Kids do love those series books and love to relate to their characters. As young readers my daughters love Amelia Bedealia, and I must admit that I thoroughly enjoyed them too! 🙂 xo

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  6. These books were some of my favourite stories Robbie as a child.. We never had many books as children.But we had a library van which came to our village once a month.. I so loved walking into that van and can even recall the smell of books it had back as a child..
    And I would dive straight for these books 🙂
    Thank you for reviving that memory 🙂
    Have a wonderful weekend.. ❤
    Hugs Sue xx

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    1. I hope that you are also having a great weekend, Sue. We also didn’t have that many books which is probably why I have so many now – making up for lost time. I loved books and had 7 library cards. I used to cycle to the library twice a week so I read 14 books a week at least.

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  7. I only wish I had kept my Rupert The Bear scarf which I had as a child. I’ve never been able to find a replacement. I’m a big fan of Rupert, and it’s lovely to see him get a mention here in the blogging world, Robbie. You may be able to find some the annuals on eBay, although I image some are rare and probably go for a lot of money.

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    1. Thank you, Hugh. I love to poke around in charity and antique shops when I am on holiday. You will be amazed at what you find and the stuff is usually well priced. I have a collection of 10 Rupert vintage annuals in good condition. I also have some lovely Noddy books.

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      1. Me too, Robbie. I could happily spend hours in charity and antique shops and at a car boot sale, although my partner is not as keen. Before I discovered the world of blogging, I spent a lot of time trading on eBay. Mainly computer games, some of which were worth hundreds of pounds.

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