The Rocky Horror Picture Show and Bill & Ted’s Excellent Adventure

It is my contention that the planet of Transexual, in the galaxy of Transylvania, is actually situated a long time from now, in a galaxy far, far away. All the evidence is there.
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Star Trek and the Rocky Horror Picture Show

While it’s not hard to imagine Dr Frank N. Furter’s reaction to meeting the Federation’s envoys (“Fresh meat!”), it’s a little more difficult to imagine how the various crews of the Star Trek franchise would react.
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Star Trek Training Exercises

I’ve had some difficulty over the last few weeks trying to find the right crossover to go with Star Trek, because so many of them have already been done to death. And then it occurred to me: so many crossovers don’t work because the contrast between them and Star Trek is too great. But such a contrast can be useful in an instructive way. Here’s a few crossovers I’d recommend to Starfleet Academy as training exercises via holodeck simulations:
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GURPS Cthulhupunk and Star Trek

You might not think that these two setting would mix terribly well, but if you do, my friend, you’re just not boldly going quite boldly enough! Lemme show you:
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Delta Green and GURPS Cthulhupunk

Pagan Publishing’s Call of Cthulhu: Delta Green setting paints a modern world of conspiratorial horror and political madness, a blend of Tom Clancy and H.P. Lovecraft. GURPS Cthulhupunk, meanwhile, imagines the future of Bruce Sterling and William Gibson with Lovecraft’s creations gnawing at its already rotting roots. Each is a compelling and horrific setting in its own right. But in combining the two, the opportunities for horror are only multiplied.
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Buffy the Vampire Slayer and Delta Green

Another fairly natural fit: Buffy’s shadowy government manipulators and those of Delta Green work very well together. After all, both groups fight the monsters in the shadows while struggling not to become more like them, and both groups prefer to operate in secrecy.
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The Implied Buffyverse

There are certain works that many would consider to more crossovers with the Buffyverse, but personally, I think of these three as implicit within it. Each of them has good reasons for being considered canonical in-universe, despite not being officially a part of it:
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True Blood and Buffy the Vampire Slayer

Not only is this a fairly obvious one, I’m still absolutely astonished that I never did a Buffy crossover with anything before. You can bet I won’t allow that state of affairs to continue.
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The Lord of the Rings and True Blood

This one isn’t so much a crossover as an examination of the former through the lens of the latter. The two worlds are obviously very distinct, but still, I can’t help wondering: what if the vampires of Middle Earth decided to go public too?
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Horatio Hornblower and The Lord of the Rings

It might seem unlikely at first glance, but it appears that the Hornblowers of Merrie Olde England are in fact descendents of the Hornblowers of the even Merrier and Older Shire. (They would hardly be the only Hobbitish family to still be extant today – the Sackvilles are still around, for example.)

But how did Hobbits become Humans? I have a theory.
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NCIS and Horatio Hornblower

Obviously, given that Hornblower lived in the 16th and 17th centuries, and that the NCIS team that is the main focus of the series works in the 21st century, there can be no direct crossover. But it’s the idea of a team of investigators working in the Navy that has a certain appeal, regardless of the era.
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The Man from U.N.C.L.E. and NCIS

To some extent, this is the other half of last week’s crossover, only focusing on David McCallum rather than Robert Vaughn this time.
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