If any work of art---great, good or middling---is to be judged foremost by its political implications or associations, we're going to end up with very, very little left on this list or any other. Works of art represent, intentionally or unintentionally, the precepts of their times, and that includes their prejudices. If we're going to discard, reflexively, American films (or literature) that have problematic representations of race, then... well... we're looking at possibly eliminating a majority of works of the 20th century.
If you institute a system in which works are evaluated principally by political correctness, you're going to have to consider all forms of political incorrectness, not just race, and not just one race. So once we eliminate the works that don't appropriately depict African Americans, we'll have consider portrayals of Native Americans, and Asian Americans, and eliminate those that do not align with our contemporary precepts---so goodbye all Westerns, among many others. Then when you're done with race, you'll need to examine the status and representation---or some would even hazard exploitation---of women in the works that remain. I think a lot of feminists (and including men) could argue the case against many films made until... this year. Then we'll move on to gender and sexual identity...
No one has to watch "Gone with the Wind" who doesn't want to. No film on this list is prescribed viewing. Setting aside its technical and historical (re: filmmaking) merits, GwtW's continued inclusion can, in fact, be an important means of discussing the racial dynamics not merely of the perceived 1860s and '70s, but of the 1930s, when it was made. This was MASS entertainment that spoke to millions of Americans, and for decades afterwards. GwtW can inform people, in a direct way, about white Americans' perceptions and representations of black Americans in the years before World War II, when there's obviously so little genuine representation of them on film. GwtW is important as a film work because this representation was certainly a fraught issue for its filmmakers, who wanted as broad an audience as possible: This was meant to be blockbuster. The same considerations of overt racism and prejudice popular filmmakers today consider when framing their films were considered then, just within a different (and yes, lesser and ill informed) paradigm. This film can be seen as an important document of 1930s racial politics that, yes, shows exactly how little say black Americans themselves had in their own representation. That alone is worth serious examination.
If you banish this film, or any film, due to political considerations, you also banish direct evidence of that era's (racial or any other) politics. Cultural critics and their critiques have their place, but they shouldn't be gatekeepers to cultural constructs and relics, providing only their received interpretations. People need to be able to watch or read works themselves, think about them, and discuss and debate them. Serious viewers (and readers) of art don't let their interpretations be determined by the works' producers. Everything is, in one form or another, a testament of the time it came from.
Having argued for GwtW's right to continue to exist, and be listed as a cinematic achievement, I'll provide my reactions to Amy's and Paul's comments ...
I actually agree with Paul's view that GwtW is foremost a melodrama. But (ref: above) that is totally indicative of the era in which it was made. Tonally, it perhaps should've been black and white. But it was meant to be a blockbuster, featuring the latest in cinematic technology in the late '30s, so it had to be in color.
Obviously, I think Paul was wrongly foregrounding political considerations rather than its technical merits, and in doing so, I think he--and many of the people commenting who have "problems" with Amy's support of the film--miss what the film is actually most preoccupied about. When you watch GwtW and focus on its racial politics, you miss what the film really wants to talk about. What Amy is arguing for, but not saying explicitly, is that GwtW is a woman's picture, because its primary concern is about a woman's role in the world.
Margaret Mitchell, as many critics and biographers have argued, was basically re-writing or re-imagining her own story. As Amy referenced, she had alternately resisted and acquiesced to the strictures placed upon a "Southern lady" throughout her life: She chaffed at them, but was never willing to completely defy them. That's what GwtW is actually concerned with: a woman's ability to chart her own course in life (and yes, a privileged, white, racist, cisgender, heterosexual woman--did I miss anything?).
If Mitchell had set the tale of Scarlett in the early, or even turn of the, 20th century, the conventions and strictures she herself had pushed against, and thereby her character too, would have been those that were generally accepted by her peers and audience. Putting Scarlett in the past allowed her---both author and character---to defy "outdated" conventions, even if stupidly romanticized, the defiance of which wouldn't seem controversial for her audience. Because arguing for women's autonomy and right to self-determination in the 1930s was a radical act, it had to be cloaked in conservatism to find a willing audience. But Scarlett's story starts with the end of the plantation South; her story is deliberately set against its demise.
If you view this film without worrying about its racial politics---they're not good, we can all acknowledge that; but a LOT of films have troubling racial and/or gender politics---you can allow yourself to view it through a feminist lens, and if you do, from the very start, you'll see it's a film about a smart, determined 16 year old who wants more than what's she allowed to have, by a sexist, hypocritical, patriarchal society. (Comparison: she's the Regina George of the 19th century, convoluting her talents and sublimating her real ambitions.)
The opening scene sets a theme: The Tarleton boys are clearly not worthy of Scarlett's full attention and time, she's just playing a game and going through the motions, pure frivolity. And all the other men in the film are not worthy of her--except Rhett Butler. The film is about the fact it takes Scarlett 20 years to become an authentic person, in modern parlance, to shed, layer by layer, her adherence to the social order and mores she was born into.
Her misguided belief that Ashley Wilkes must be her mate can't be understood properly unless you look carefully at socio-economics. Scarlett's father was an Irish immigrant, and Catholic. The O'Haras were rich planters, yes, but weren't by any means the leading family in the county: The Wilkeses were. (In the novel it's made explicit the Wilkeses were from Virginia and certainly Protestant.) Marrying Ashley---in a society that only allowed women marriage as a life's vocation---was, for teenaged Scarlett, the brass ring, the greatest achievement she could fathom, although clearly Ashley wasn't completely ill suited for her. But when all you can do is get married, marrying the richest and most important man you can is... most important. (For a real life 20th century comparison: Diana, Princess of Wales and Prince Charles.)
The war, the South's defeat, the end of slavery, etc. provide opportunities for Margaret Mitchell to put Scarlett in situations where she has "no choice" but to operate as a strong, determined woman making her own way. External forces can be blamed for it, not Scarlett's own will, which makes her still acceptable to readers (and later viewers) as a lady. As Amy points out, though, she is in the fields working as hard as everyone else, but more importantly as hard as a man. She starts a business where no man could see the opportunity to do so. She runs the business with a better eye on the bottom line than any man does. This film is a fantasy about a woman making in a man's world. But that story set any other time would've been unappealing to then-contemporary audiences, and still melodrama was required to necessitate the story and her actions. Her first two husbands die because it's the only acceptable means of disposing of them for the time period; but what Mitchell is really doing is discarding men from Scarlett's life when they're no longer of use to her.
The men in film, with the exception of Rhett, are dolts, blowhards, or purely ineffectual. (Although Scarlett loves her father, he's presented as leading the foolish "debate" about the South's chances in the early scene Amy references, and falls apart during the war; the book makes it clear it's her mother who ran the plantation.) Women in GwtW are the role models, the ones who are noble and good---Mrs. O'Hara and Melanie---or prevail and triumph---Scarlett and Belle Watling. And yes, this includes Mammie and Prissy.
Mammie is clearly presented as a kind, smart, affectionate character throughout the film. She's never made to look ridiculous or the fool. She's consistently the only one who's "got Scarlett's number." And as Amy points out, in the pivotal scene with Prissy and Scarlett, Prissy's actually no fool. Whether Mitchell and filmmakers recognized this consciously or not can be debated, but Prissy is a 19th slave member of the #resistance. She's a teenaged girl, separated from her family and friends, who's powerless, but she wields what power she has to manipulate Scarlett and those around her. She only acts the fool to survive and get her way, I would argue.
Definitely Big Sam is an African American character whose representation is absolutely problematic. It's definitely overtly racist. Yet, it's partially due to the fact no man in this film other than Rhett is credited with genuine savvy. Sam is discriminated against and badly characterized both for the color of his skin and his sex.
I'm not even a mega GwtW fan---it wouldn't be on my personal top 50. I hardly even think about it when I think of my favorite films. I last saw it 15? years ago when it was re-released in theatres. But I hope this post (which I know is long) evinces the fact there's a lot in the movie, and a lot to be said about it, and foregrounding the discussion of slavery and racial politics routinely seems to inhibit, or prohibit, a discussion of everything else that's going on in the film. Focusing primarily on one of many elements is overly reductive, and places contemporary standards on it that are going to be impossible for a LOT of films from the 20th---and 21st---century to withstand, if you're consistent in applying them.
The film isn't attempting to glorify slavery or even segregation because it doesn't even want to talk about race, in actuality. It's a trope that's employed because of its setting. But just because a work doesn't want to discuss something doesn't mean you don't, and because Mitchell and filmmakers chose the Civil War as the context for the film, there certainly should be discussions of race in relation to it. I'm not arguing against that. But talk about racial representation in it and contextualize it to the time the film was made, and accept the fact you cannot unmake the past. I'm gay. There are a LOT of films and media I watch that make me personally cringe when I see them. But I don't advocate for their exclusion from our consciousness, because they accurately, for better or worse, represent the eras in which they were made, and we need to remember how things were---really were---and not how people want us to remember them. And the best way to do that is to read and watch things ourselves, consider them, and discuss.