Rupert Bear has been running in The Daily Express since 1930 and is still there today. His annuals continued through paper shortages in World War II, because parliament gave special permission.
He's a friendly little bear, originally brown until he became his current, iconic white to cut inking costs. (Oddly, he's white within this annual, but brown on its cover.) He lives in the village of Nutwood, which is inhabited by a mix of humans and human-like animals that are completely human in every respect but the obvious. These include Bill Badger, Podgy Pig, Gregory Guinea-Pig and so on. Furthermore, Nutwood Forest contains talking animals, birds, etc. that are realistically drawn and written in every respect but their ability to product human speech. Rupert also sometimes visits places like Dreamland, Toyland, Mirrorland and Timeland.
Rupert Bear can be surreal, but it's a gentle, 1930s sort of weird. It also has a unique page format, which was developed by Rupert's second artist, Alfred Bestall. (Bestall drew Rupert every week from 1935 until 1965, but was still doing Rupert stories and artwork even in his nineties.) It's akin to the old style of comic strips that you can see in other 1930s publications, but more complicated. Each page can be read on four levels:
(a) each page has its own separate title (e.g. "Rupert Receives a Box", "Rupert is Blown Over"), in addition to the story's umbrella title.
(b) illustrations, usually four per page and with no word balloons or sound effects. Everyone draws these in the style of Rupert's creator, Mary Tourtel, although no one's a perfect clone. Tourtel's Rupert was more like a real bear, for instance. I'm mildly curious about her Rupert stories, because apparently they started getting macabre after her husband died. When Bestall took over the strip, the children's editor told him "no evil characters, fairies or magic".
(c) rhyming couplets beneath the pictures, for younger readers. If you're reading these, you're also looking at the illustrations.
(d) a block of more detailed prose at the bottom of the page, like a short story. If you're reading this, on the other hand, looking at the pictures is more of an afterthought.
The plots are more complicated than you might expect. There are only five stories in this 116-page book, although admittedly there are also a few filler pages. ("Rupert's spinner game", "How to make a paper glider" and "Magic painting puzzles and games".) The Magic Painting pages are famous, but also a nightmare for collectors. You "painted" the pages with water and colours appeared... and the annual instantly halved in resale value as the pages got all wet and wrinkly. Going through in order...
1. RUPERT AND THE DRAGON FLY
If it weren't for the "velly solly" Chinese dialogue, this would be fine. Ironically, Tigerlily (and the Chinese Conjurer and Pong Ping the Pekingese) were progressive portrayals at the time. They're Rupert's friends and reasonably well-rounded characters, so for instance Pong Ping here is helpful and nice, but also smug and extremely competitive about winning the rose show. In addition, they're drawn realistically. Tigerlily is a lovely child and has a pretty dress.
Today, though... bloody hell.
"Tee-hee, what idea! Some day, perhaps, when me learn spik English good me teach Chinese, but not yet!" She says "muchee" and "velly". It's an accent mish-mash, including Chinese, the biggest cliche of Native American dialogue (using "um" as a pronoun) and I bet probably a bit from other places too.
I quite like the plot, which involves a tiny, smoke-puffing Chinese Dragon Fly.
2. RUPERT AND THE ROBINS
Involves all the Nutwood robins turning yellow (AND TALKING TO RUPERT ABOUT THIS!!!) and a flight in a toy airplane up to Santa's castle in the clouds (WHAT??). This Santa is a dick. "I've never heard of such a thing. An English village with no robin redbreast! Nutwood doesn't deserve to have any Christmas. I must think seriously about this. Go back at once, Rupert, and tell your friends that if they can't put things right I may not visit them at all."
Oh, and Santa's "elf" is a golliwog. Yes, that's right. He's called Golly. I'm sure Bestall would have been horrified beyond measure to have his work called racist, but holy shit. (Incidentally, I've just been quasi-defending the Chinese characters in the previous story, but no one anywhere tries to defend the "Coons" of "Coon Island". See the Rupert annuals of 1954 and 1960.)
3. RUPERT AND NIAGARA
Rupert gets a letter from his Uncle Grizzly. That was weird. Rupert and his parents look cute and harmless, but that for me was a reminder that they're one step away from apex predators that can weigh a third of a ton.
Anyway, the letter talks about Niagara. This will prove an inspiration for Gregory Guineapig (sic), who's an obnoxious brat with nuclear-strength attitude but has been drawn to look adorable and perfect if you've ever kept guinea pigs. The face and body language are spot on.
4. RUPERT AND THE BAD DOG
I didn't like Rupert's knee-jerk scolding of Jock the terrier. The ending has Jock still being scared of Rupert even when the bear's being nice to him, which seemed reasonable on the dog's part. Meanwhile, Rosalie the pig makes Gregory Guineapig look calm and thoughtful.
I'm starting to see a pattern of stories about problem people.
5. RUPERT AND THE CORAL ISLAND
...has female supporting characters! That's not unique, admittedly, but I had noticed that Rupert's animal friends tend to be male. This story, though, has Beryl, Pauline and Janet, the girl guides. (They're based on three girl guides from Bestall's church who asked him in 1947 if they could have their own adventure with Rupert. He obliged and they're still part of the series even today.)
Rupert goes to the seaside, meets a Merboy and has a fish tow him to a coral island.
In summary... weird and unintentionally racist. (In 1985, Express Newspapers started reprinting old Rupert annuals, but this is one of the ones they excluded because of "politically incorrect content".) That said, though, I've always liked Tigerlily (or Tiger Lily) herself. She's nice. The stories aren't always particularly dramatic, but there's a good mix in there. Some of them are whimsical and some are driven by outrageous brats who need slapping.
At times, the art can be jarringly realistic. When Bestall draws a guinea pig, he draws the hell out of guinea pigs. When animals are in human clothes, this sometimes yields characters who are almost terrifyingly ugly. They're not Disneyfied. A pig in a dress will, literally, be a pig in a dress. Thus, for instance, Algy Pug could break mirrors and Rosalie Pig is yowzers.
I enjoyed these stories as a child. Not just Rupert in general, but this actual book. We had two at home and I unearthed them the other day. Today, I thought they were okay. Not gripping, but nice.
After I'd finished this book, incidentally, my eight-year-old son read it too and enjoyed it.