Two sets of narrators, Basil Rathbone and Bing Crosby, narrate stories featuring popular characters from their respective countries. Rathbone reads an adaptation of 1908's The Wind in the Willows by Kenneth Grahame from his native Britain wherein spendthrift and manic Mr. Toad is swindled into making an idiotic deal for a stolen motorcar for which he is then framed for the theft, necessitating intervention from his friends Mole, Ratty, and MacBadger. Bing Crosby then narrates an adaptation of 1820's The Legend of Sleepy Hollow buy Washington Irving which tells the story of a schoolmaster named Ichabod Crane who uses his social connections and community prestige to indulge his appetites as he competes for the affections of a wealthy farmer's daughter named Katrina against the bullyish town hero Brom Bones until one Halloween night, the superstitious Ichabod finds himself pursued by the Headless Horseman.
The final package film produced by Disney during the 40s. Originally intended to be its own feature length film, Wind and the Willows was truncated to featurette length not only because of resource scarcity at Disney studios at the time, but also because Walt Disney did not think the material was strong enough to justify a feature film. Initially intended to feature three segments, the third segment, and adaptation of Roald Dahl's The Gremlins never made it to production with only Sleepy Hollow and Wind in the Willows now comprising the release. While it still has many issues that plague Disney's other package films, The Adventures of Ichabod and Mr. Toad is far and away the best of these package features by virtue of showcasing literary characters from the U. K. and United States in grand manner with its library set framing device carrying a dignity and weight that really hasn't been seen in these film's since Fantasia (though admittedly it falls short of it).
The first segment, an adaptation of Wind in the Willows where we follow the madcap hijinx of Mr. Toad as he squanders his inherited fortunes of expensive misadventures whose fallout he leaves to his trusted friends to clear up is well told with Basil Rathbone's voicework giving weight and authority to a largely comic narrative with Toad's misadventures landing not only himself into trouble, but also those around him. At its core it's a decent story about friends helping a troubled friend out of trouble, but the ending where Toad reverts to his foolhardy ways blissfully unaware and unrepentant for the trouble he caused himself and his friends is definitely an odd note to go out on (but probably appropriate). The short features clever dialogue exchanges and strong animation with this world of humans and animals not only interacting, but set to scale in a unique and visually striking creative choice.
The second segment is really good and is a strong ghost story. What really fascinates me about the adaptation of Sleepy Hollow is in how our protagonist is when you step back and look at him a pompous, avaricious, and opportunistic character who is often ill remembered as an innocent who falls into the supernatural fate that befalls him. While on the surface it seems like the rivalry between Brom Bones and Ichabod would ordinarily favor Ichabod as the default "good guy", Ichabod when he falls for Katrina is fantasizing more about her inordinate amount of wealth and her father dying than he is about Katrina herself. Brom Bones is certainly a very brutish character who seems to have more muscle than brains, but at the same time he does seem to be interested in Katrina purely for herself rather than her money as Ichabod is making an interesting character dynamic where the Headless Horseman payoff feels more like comeuppance. The one drawback I'd give this short is in the casting of Bing Crosby who's fine I suppose, but his rather campy approach to the narration coupled with his upbeat singing that breaks the tone of the short (particularly in the ghost story set up for the Headless Horseman) creates a jarring disconnect. Unlike the rather silly Wind in the Willows where Basil Rathbone's was played probably more serious than the material called for, here Bing Crosby overly camps up the material in a rather head scratching manner that while it doesn't undermine the short that much still is rather head scratching in the creative choice.
Like other package films from this era of Disney there's some good elements and some weak elements. I still say this is probably the strongest of the package films produced during this particular era of Disney film history thanks to the film's focus on literary classics and attempting to give the audience well-constructed featurettes, but in the case of Wind in the Willows the material was okay if unremarkable, and with The Legend of Sleepy Hollow it creates a memorable set of characters but undermines itself with Bing Crosby's rather distracting presence that feels like it was added solely to cater to contemporary tastes. Mostly positive if messy experience.
