The Birth of a nation (1915)
Great oppprtunity to push the envelope and take the audience out of their comfort zones.
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Hinder90 commented
I think a two skilled riffers who can avoid being preachy, an African American that is that balance of no BS but also not taking themself personally too seriously and a well-meaning but smart/funny cornfed Midwesterner (cough MIKE cough) could turn this silent movie powder keg into the permission to mock ugly history rather than give platitudes. I know it’s a really tall order and not for the faint of heart, but I’ve seen Mike do this kind of stuff well so if you could get a talented black comedian who “gets” riffing (jfc what am I even saying!) this could be unforgettable!
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Dan Asnis commented
This would need to have African American riffers.
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Joel commented
I understand it's a silent film, so that would give them less to work with, and also given the nature of the film and the modern political climate, i think it would tie the riffers' hands quite a bit at the risk of, for example, having their office in California burnt down by a riotous mob.