I held over the Christmas story of December 1939-January 1940 as this was reprinted in the 1942 Annual, Rupert and the Wrong Presents (22 December to 20th January). Rupert wrote to Santa asking for a motor boat and received a pair of boots with wings. His father received a flute instead of a pipe. Thus begins a cunning tale. Wearing the boots, he found himself flying. The flute summons a wooden bird. The bird is so alarmed at the wrong presents being in the public domain (flight and secret signals) that Rupert is brought to Santa's castle (representing the prime minister), helped by a toy hurricane. The distribution of top secret ordnance has alarmed the Christmas authorities, and Rupert is clearly doing a service to national security. (The flying shoes would have been much more fun than a boat). A golly (no longer a gollywog in the reproduction edition, just golly+ white space) is the doorboy, the 'secretary' is a bureaucrat with a dolly-bird typist. Rupert is sent with a covering letter to Santa who explains, "You see, Rupert, ...I had heaps of extra work to do last Christmas, because lots of children were spending Christmas in other people's homes, and I had a job to find them at all". The evacuees. He is given the right presents and is taken home by plane.
A story from 1940 centres on a scarecrow, Odmedod (6th April to 22nd May 1940). Who can speak and walk around, as all British children know. He scares birds by day, and is off duty at night, so goes to play with Rupert. Rupert loses Algy when they run from a farmer, who thinks they are damaging his fruit-trees. Rupert meets the local plod, Constable Growler who is on the watch for spies. They are close to the sea. Rupert searches for Algy and comes across Osmedod. They shelter in a hayloft when two suspicious men come in with a lantern speaking a foreign language. A good clue. Rupert follows, and hides behind a water butt. Osmedod gets trapped in the loft when the ladder is taken, so Rupert has to take his place as duty scarecrow. Algy rescues him and takes him back to the barn where the two spies come out of a trapdoor and kidnap Rupert and Algy. They go through the tunnel, prisoners, which comes out in a cliffside and flash towards a waiting boat. The chums are rescued in the nick of time by Osmedod, who scares the spies who take him for a ghost. They report back to Constable Growler, who goes with the farmer to find the trapdoor and the cliffside tunnel. All ends happily, Osmedod back on duty, the farmer allowing Rupert to pick bluebells for mother (it is Eastertime) and Rupert promises not to damage the fruit-trees.
Rupert and the Cartwheels (23 May to 22nd June 1940) is more puzzling in its putative war connections. True they meet a friendly armed guard, and restore a castle to its aristocratic owners by finding lost treasure (Edward Trunk's cartwheel plunged him into a hole with a rotten cover). One picture looks like everyone giving a Nazi salute, as a prelude to cartwheels that did not happen, replace by a cunning diversion through a fence where Rupert and Algy almost failed, Edward Trunk did fail and had to invent a brilliant new strategy. Their journey to that point had been through water first, to a defended citadel in need of treasure, which they duly found to save the day. The evacuation from Dunkirk began on 24th May until 4th June. Given that Bestall may have been submitting his copy gradually, his simple follow my leader story planned when, to be sure, the British army were in dire straights was able to provide solace to readers. As the army were being ferried across the channel, Rupert and his chums were rescued from the water and managed to solve the problem. So would Britain hold out, and find the strength to succeed.
Rupert and the Little Plane (12.4.1941-19.5.1941) is an optimistic tale of a plane that runs without petrol. Fuel was rationed, and the convoys were struggling. The little plane was a mixture of autogyro and hand-cranked geared propeller.When Rupert was tired of cranking, the autogyro brought them plane gradually down. Two spies (the fox brothers) try to steal it, but are foiled as Rupert has kept the winding handle. A simple tale with a simple message: these are serious times. Be prepared for trouble.
Finally, the 1942 annual contained three pre-war stories. The last one, Rupert at Sandy Bay, looked back to the good times of seaside holidays, before beaches were filled with mines and barbed wire.
The next stories in 1940 were carried in the 1943 Annual. Rupert and Tiger Lily, 24 June to 3 August) is our first introduction to this Chinese magician's daughter. She posed problems in showing too much of her magic ability in school. This was clearly inappropriate and she soon manages to show much less character. She is however a very clever girl who learns the important message that schools are about working and not for thinking.
Rupert and the Banjo, 6.8.1940 - 21.9.40 is the August Sandy Bay offering, notwithstanding that no child was allowed near a seaside this year. The war doesn't intrude: it is a story of helping others and overcoming two rough pirates who stole the banjo threatening the fairground folk to lose their livelihood. The pirates were certainly depriving many people of lives and livelihoods by attacking the convoys, but this is only a distant echo.
Rupert's Good Turn, 24.9.1940 - 1.11.1940 is about forgiveness and solidarity. A farmer is annoyed with the chums for trespassing; and Rupert is annoyed with the fox brothers for playing a trick; but they save the farmer's haystack from fire, and negotiate the release of the foxes. Annoyances are shelved in the face of the greater danger, fire. Outside of the strip, the Blitz was under way, and the Battle of Britain was on. Fire must be tacked, and allies must be friends and not foes.
Rupert and the Piper, 2.11.1940 - 16.12.1940. Rupert finds a pipe in the 'lumber-room' and shortly afterwards is given The Pied Piper to read. He falls asleep (the readers don't yet know) and with his chums meets the real Pied Piper who draws them all to become prisoners in his castle. Rupert alone resists to pull of the music, and sets off to rescue them, against the advice of the red squirrel. He meets a friendly giant who devises a form of rescue - the throws Rupert overarm, with a parachute to break his fall. It just fails, but Rupert wakes up in the nick of time. The Battle of Britain was technically over at the time this serial began, but was taking place when the story was conceived. The chums would be rescued from Hamelin Castle (suitably Germanic) but air power, supported by superb allies (animals, birds and a giant). By the end of the strip, he could honestly say that the danger was over (Rupert woke up). Rupert becomes a role model for resistance: never despair, never go with the flow, be agents for change, have a go, or as Churchill said at the time, 'Go To It'.
Rupert's Birthday, 6.1.1941 - 15.2.1941 - Rupert wants to grow up, literally, it proves a painful experience.
Rupert and the Iron Key,17.2.1941 - 10.4.1941 - thieves (an outside and an insider, (a spy and a fifth columnist?) try to rob a castle, but Rupert foils their plan and finds the treasure, a gold suit of armour (the invaders are repulsed, as they were on 17 September 1940, and Britain refinanced, armed and defended).
In Rupert and the Black Moth, 20.5.1941-11.6.1941, Father Bear is digging for victory but a tame black moth eats his cabbages. On advice from the Chinese Conjuror, Rupert takes it back to the Yellow Mountains. This is achieved through a cave system (that is, deep in the imagination) and Rupert is given the reward he asks for, a replacement for the cabbages. There are some negative stereotypes of Chinese and a black man (but it is an Ali Baba reference) but the tale demonstrates that if everyone honours the rules of ownership, then there will be food for all.
Rupert and the Circus Dog, 12.7.1941 - 15.8.1941. The ringmaster is a bully, kidnaps a valuable new performing monkey, and with Rupert's help is sacked. The message is that kindness gets the most out of people.
Rupert's Big Game Hunt, 16.8.1941 - 10.10.1941 - a whirlwind destroys a circus, and Rupert rounds up the animals. The moral is: do not panic in a face of disaster but sort things out.
Rupert's River Adventure, 11.10.1941 - 14.11. 1941 - Willie and Rastus, the mice, are kidnapped on a boat trip, imprisoned in a castle tower on an island, and are released by Rupert and Podgy in a 'great escape'.
Rupert and Golly, 15.11.1941 - 5.1.1942. A golly from Santa's workship tries to punish Rupert and Bill Badger by making them help with the toys (mostly painting fighter planes). They really enjoy this, and the bureaucratic golly is very cross. Santa is amused at the come-uppance of the bureaucrat. Apart from the anti-bureaucracy dig, there is a message that punishment can become enjoyment, and we can deal with punishment by refusing to feel punished.