9. Soul Man (1986)
Soul Man, released over 25 years ago, is still considered one of the most racially charged comedies ever made. The film tells the story of a young white man named Mark (C Thomas Howell) who takes copious amounts of tanning pills so that he can attend Harvard Law School on an African-American scholarship as a young black student. From there the film attempts to make Mark's journey masquerading as a black man in modern day society a plight and a social commentary on how certain classes of people treat minorities. However it often fails in doing so, coming off as heavy handed and unfunny with its depiction of stereotypes for cheap laughs. One of the most cringe-worthy plot points in the film is the fact that Mark falls in love with an African-American student named Sarah (Rae Dawn Chong) while in school. As he slowly begins to regret making his decision of faking the system and ultimately confesses that he is actually white, he is ostracized by Sarah initially upon discovering he is white. The film misses the point of trying to say that nobody should be judged on their skin color alone, yet she rejects him for being white. This film is one of the original race swap comedies (True Identity, The Associate, White Girls among others) and it is certainly one of the worst.