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King of the Hill most definitely does have problems viewpoint-wise. Basically you're both right. On the one hand, there are plenty of cases where Hank is supposed to represent outdated views and you're supposed to be laughing at him for it. Like, for instance, when he's talking about how poisonous MTV is. However, there's also plenty of times when you're legitimately supposed to be agreeing with him. This is usually in cases where they'll take an issue, give an incredibly exaggerated side of it that goes too far in one direction, then portray it as being the bad side. The problem is, the only other side we have is Hank. By implying that the other side is totally nuts, it's implying that you're supposed to be on Hank's side when really both are awful.
You see a lot of this fight against ultra-liberalism and "political correctness" (a term that makes my skin crawl) which would have a point if the answer didn't seem to be "so let's not even begin to think about this just like Hank. Let's just say it's silly and move on". Like the episode where the school gets a diversity counselor or whatever when the kids are supposed to be working on a school fair. The idea in this episode is that the kids, who are a mix of a variety of ethnicities, were working together just fine without someone coming in and talking to them about diversity. The counselor in this show is laughable and is concerned only with heaping guilt on the kids without actually discussing the issues at hand. Nobody would say that this guy should be the hero in the episode. But the show seems to be pushing the idea that kids don't need to worry about diversity because hey if you don't talk about it they work together just fine! It's equally laughable to me that somehow this whole school has no issues with racism whatsoever and that if you just leave kids to their own devices they won't ever be racist or ignorant of racial issues. This is total bullshit. I know that King of the Hill is a comedy show, but that just means that it doesn't need to be "tackling" real life issues that it's not actually giving a second thought about. I've seen every episode of King of the Hill several times, and I can definitely say this happens far, far more than it needs to. Nearly any episode that takes on some sort of social issue mishandles it this way. Also, watching KotH with my dad, it's clear that a lot of the people watching it don't even get that Hank isn't a hero 24/7. I see him identifying with things in Hank that were meant to be laughable, but he takes them literally and seriously.
So yeah, there's a lot of things in the show that are ultimately sending a really regressive message. Does that make it a bad show? No, as long as you aren't taking any political ideas away from it. It's still really cleverly written and funny and whatnot. But does it push conservative values? Occasionally yes, and when it doesn't it's still pushing Not Progressive Ones(tm).
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