Someone with more energy than me should start a "riskiest episodes" thread, focusing on episodes that, while not acclaimed as Great,* do take artistic or dramatic risks that pay off--or don't. I think that's a lot of what DeafPoet is rightfully praising "Family" for.
Now, a lot of this is going to be in the eye of the beholder. Is something like "The Empath" (to say nothing of "These are the Voyages") going to be considered risk-taking, or just poorly-executed?
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The capital G is me deliberately breaking the rules of capitalization to make a point. Just saying so because this is the Internet, where nuance doesn't usually go very far.
"In The Pale Moonlight"