The box spine image is not upside down it was just printed that way.
This is a short video for the Paramount Pictures Star Trek Adventure at the Universal Studios Tour attraction. Most videos were 8 to 10 minutes long
At the time "Star Trek The Next Generation" was on TV and this slipcase was advertising it.
Each tape is personalized to the customer who participated in it and paid for it.

The Universal Studios Hollywood theme park featured a Star Trek-themed attraction. The attraction regularly selected 10 volunteers from the audience and placed them into a Star Trek story line. The participants were dressed in Star Trek costumes and placed on sets, and coached to deliver scripted dialogue in several scenes. The scenes, which were recorded on video by Lilly, were quickly edited into a short film, the storyline of which was loosely based around material from the Star Trek films. The finished video was then shown to the audience, and the "actors" had the opportunity to purchase a copy of their video. The attraction existed from 1988 to 1994 and was replaced by The Flintstones Show.