Yep. Wizard of Oz premiered in August 1939, and Ovaltine ceased their sponsorship of the Little Orphan Annie Radio show in January 1940, so that kind of narrows down the speculation a bit for those of us obsessed with facts.
I've been told there are some interviews with Shepherd who related that it wasn't supposed to be set in a specific year but was a compendium of childhood events and memories rather than a apecific narrative of one year's Christmas events. I'm willing to accept that; I've just never been linked to, or shown these interviews by the people who've told me they exist. Furthermore, Jean Shepherd was born in 1921, so it stands to reason his early childhood memories would have been well before 1940.
I once slowed down the scene and you can take a gander at the Orphan Annie Decoder pin. I think it had the year on it. Of course, such things are limited by the ability of the prop department to get the proper pin!
I always assumed the year to be 1939, the year the wizard of oz premiered. They make such a big deal about it in the movie.
Decoder pins: http://www.radioarchives.org/annie/
Thanks for all the info! Interesting true “trivia”. Well, I guess I reaasoned pretty well about it. I didn’t even pay much attention to the cars, which is 1 of my fortes and something I’m always checking to figure out what year...
As far as him making a “composite” story, that’s fine and believable; but making a story like this you put it into 1 year.
Of course, sounds like Mr. Shepard’s year should’ve been more like 1929!