Which one of the two movies has less offensive stereotyping of African Americans?
Maybe neither.
In Song of the South the premise is that a lovable old black man tells stories to black and white children (in his dialect of the time … a black, southern dialect from … what was it? … during, or just AFTER the time of slavery?).
Some stereotyping might offend some. Generally if one finds some of the stereotyping to be negative.
“Cabin in the Sky” was probably a watershed Hollywood movie with its all black cast showcasing enormous talents … and an out-of-fashion per our day morality tale that presents a right and a wrong, the spiritual battle between the devil and humans, the power of prayer, etc.
That said Cabin does show that there is criminal activity in town as well as the virtuous church. Meaning that some in the cast were … black and criminal (gamblers, cheating gamblers, wild juke joints, gun-carrying thugs, all the way to … the demons!). Gabriel the Angel and Petunia are paragons of virtue though … and counterbalance the doings of Georgia Brown (the BAD girl temptress).
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I havent seen “Song of the South” since childhood … over a half century ago. CAN one see it? Did it (like the slavery period) ever really exist?
Being a 5 year old kid … I just liked Uncle Remus (and men who were nice to kids). His tales were just entertainment for the kids.
Even the (notorious?) tar baby story … where Brer’ Rabbit’s anger gets the better of him and he attacks a (scarecrow like) “tar baby” fashioned by his rivals and is thus caught … didn’t strike 5 year old me as REALLY being some negative thing about black people.
The “tar baby” made of tar, would be black (of course). Remus the story teller was black and spoke in a dialect more like the Southern characters of the 1800s recalled in Mark Twain’s novels … than Shakespearean English.
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There are images and actions that might make modern day US wince a bit - conditioned as we are to spot (negative) stereotypes - especially racial ones - with a proper modern reaction. But Disney and Vincent Minnelli were probably opening doors for blacks in Hollywood with these efforts … and probably presenting much more GOOD in bringing peace between the races (and regions) per their intents (IMO).