I have thought about this quite a bit and I believe that this particular pairing, Nietzsche with Family Circus, is at least especially good (if not uniquely good).

For me, Family Circus was never really enjoyable. Somehow that makes Nietzsche Family Circus even better.

My guess is that if you start pairing things at random, you will on average going to get something much, much worse than this. An understanding of why this is true promises to elucidate the contemporary condition, I suspect.

That's one of the fun little oddities Gary Larson talks about in "The Prehistory of the Far Side", where syndication captioning errors led to a couple of swaps of Far Side and Dennis the Menace cartoons, with weird results.