I'm almost sure I remember some paperback books printed in the sixties or seventies where the image of the Enterprise was upside down. Anyone recall what those might have been? 

I don't recall seeing any books or paperbacks with an upside down Enterprise, as such, but I remember a few of the rougher sci-fi pulp magazines (printed on recycled newspaper, no less) doing a feature here or there on Trek....and they'd sometimes screw-up and post a picture of the Enterprise that way.
Once I came across a paperback...maybe about 1975 in an obscure little Canadian town. It was purple, it wasn't about Star Trek at all but rather a collection of sci-fi short stories and on the cover was an AMT Enterprise (sliver) altered to give it a weird futuristic look. I remember instinctively being drawn to it but despite my age at the time (9), I knew enough that it had nothing really to do with my beloved Trek...and that my dollar and change was better spent on other entertaining things.
Ummmm... did you ever see the Enterprise depicted upside down in the series? I don't think so. It doesn't make sense to show it upside down in printed media either."Up" and "down" would be arbitrary in outer space.
Wow, that corruption of the Enterprise on the Galaxy 666 cover is astoundingly awful!![]()
Richard J. Anobile's black-and-white fotonovel of STAR TREK II did show an upside-down Enterprise on one page. Maybe it's because the Reliant looked upside-down to begin with. Not quite the flawless efforts he earlier put in book form with PSYCHO, ALIEN and OUTLAND. Those were the days....
You're not imagining things, BoredShipCapt'n.
I remember seeing them, too.
So far I've only tracked down one example:
"Mudd's Angels" by J.A.Lawrence.
First Printing in May 1978
It's one of the Bantam ads in the back of the book
advertising their other Star trek titles.
The top line reads: "THE EXCITING REALM OF STAR TREK"
and right below it is the upside-down drawing of the Enterprise.![]()
That's a pic of the renovation done by the Smithsonian. Note prominent grid lines.
Wow, that corruption of the Enterprise on the Galaxy 666 cover is astoundingly awful!![]()
Especially that 2 inch penis where the bridge was.![]()
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