I think the most sympathetic portrayal was in _The Skin Game_, a rather clever piece in which James Garner did a reprise of his Bret Maverick TV character partnered with Louis Gossett Jr. Garner would sell Gossett in the daytime and come back and rescue him at night, when they both make off with the cash. However, in one of these transactions, John Brown comes through and makes off with a bunch of recently sold slaves, and the two rouges wind up having to take the whole thing much more seriously. Light entertainment, perhaps, but a nice reflection of the mood of movie goers in 1971.
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