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I think there are three schools of thought when it comes to video requests. One type is interested primarily in Chuck dissecting a work and providing his perspective. Most would fit in this catagory. The next is wanting to see Chuck trash something they don't like/awful. These are rarer, but the slipped through the door series would seem to fit. The last is what I call the nausea bracket, where the request just to see Chuck's reaction.
I'm willing to wager that there haven't been any requests of the third type, at least on purpose. I think there have been a few that touched him the wrong way (Real Life, the rapey Stargate episode, and Kannazuki no Miko), but I don't think anyone meant to piss him off.
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A friend of mine made some requests a while back. At the time, he was considering requesting a visual novel with a large amount of graphic content. This wasn't because he wanted to see Chuck's reaction, but because it did interesting things with the story.
He ended up changing his mind because 90% of all the Gameplay footage would end up looking like this:
And VN gameplay footage was boring enough to begin with.
This was something that ticked the other box, interesting to dismantle SF. Breaking Chuck's target material rules, just to see him get mad? That's just mean.