A Gentleman's Gentleman（1941）

Mickey Mouse lies in bed like a lord, getting served breakfast by man's (and mouse's?) best friend Pluto as gentleman's gentleman. Next duty is to fetch the paper, but also pay for it with a coin for the vending machine, and those round things have a nasty habit of escaping a dog's teeth and bouncing over the pavement till they end up in the gutter. After enough attempts to fish and spend the penny, Pluto has a newspaper to carry the same way. The wind has a nasty way to get a better grip on page after page then the dog, so by the time he delivers the daily dose of printed news it's an embarrassingly muddy mess.