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So, in the Donald and Goofy cartoon "Billposters", Donald and Goofy both whistle and sing Whistle While You Work a couple of times. I know that the Disney characters would sometimes sing popular songs of the time, but it was a bit jarring to hear one from a Disney film. Although it was probably supposed to be a joke, it almost felt like self-promotion, and, well, it was just kinda weird. Does anyone know of any other early instances of this sort of thing?

Several Goofy appearances/shorts often features him singing the first few bars of "Oh the World Owes Me A Livin' ", which was first used in 1934's Silly Symphony "The Grasshopper and the Ants" as well as Shirley Temple's film in the same year, Now and Forever.

"Pluto's Blue Note" features him lip-synching to Bing Crosby's cover of "You Belong To My Heart", which was originally in The Three Caballeros.

And of course, the "Disneyland" television show always opened with "When You Wish Upon A Star".

I'm sure there's more, though I can't really think of them off-hand.

albert

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Zip-A-Dee-Doo-Dah from Song of the South is sung by Donald in Soup's On (1948) and by Goofy in Man's Best Friend (1952).

I forgot about World Owes Me a Living. "On Ice" is at least one example where that one's used. Thank you.

Two more:

Whistle While You Work is also in Honey Harvester (1949)
and
When You Wish Upon a Star is in Donald's Dilemma (1947)