Off hand, I'd say it was one of the first personal listening devices.The horn in front was probably the speaker- because back then it wasn't cool to force people a hundred feet away to hear your noise (also the volume only goes to 8).Then you have the antennas and tuner on top.
I figured it for a time machine. There's a dial on the side of it to select the date, some wires and what-not to create a worm hole. I also assume he is checking the date on the newspaper to make sure his is where, er... when... he wants to be.The only thing I can't figure is the miniature saxophone on the front of the hat.
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