Disney’s The Legend of Sleepy Hollow

The Disney version of The Legend of Sleepy Hallow features the vocal skills of one Bing Crosby. I grew watching re-runs of Hope and Crosby Road Movies, Bing Crosby Christmas Specials, and Bing Crosby Florida Orange Juice Commercials. One of my all time favorite films is White Christmas, which featured Bing Crosby and Danny Kaye-Bob Hope must have been busy entertaining the tropes somewhere.
Now Bing Crosby always played a kind and gentle soul, soft spoken and quick to forgive any offense. His children would later write books along the lines of Mommie Dearest telling the world that Bing was a right bastard. But they couldn’t destroy his body of work showing the world the man we all loved, even if that man never really existed.
The Legend of Sleepy Hallow is a simple tale of a greedy school teacher, the town bully, and a lovely girl whose father happens to be rich. This short film features several songs by Bing Crosby and is told solely in his voice. Having seen this silly bit of business many times on The Wonderful World of Disney, I always liked it. But it is not exactly scary. There is a long lead up to the famous chase scene of the Headless Horseman going after Ichabod Crane and his poor skin and bones horse. Hey, they had to put those silly songs somewhere.
Still, there are a lot of flashes of later Disney successes here. The Town Bully of Sleepy Hallow is clearly the father of the Town Bully in Beauty and The Beast. And the fair Katrina is clearly the mother of all Fair Princesses to come.
But the ending is a little different from most Disney endings. We are left to wonder if the school teacher lived out his life surrounded by children and a plumb wife who is was a good cook, or whether he died at the hands of the Headless Horseman. Of course, it is Disney, so he must have lived happily ever after, right? Muhhahahaa.

Jon Herrera

Jon Herrera

Writer, Photographer, Blogger.
Jon Herrera

Latest posts by Jon Herrera (see all)

Writer, Photographer, Blogger.

Posted in disney, halloween, sleepy hollow

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