2001: A Space Odyssey (1968)

Set In
2001, according to our research of the title on the DVD case
The Premise
Mankind has begun colonizing space (awesome), leading to the discovery of an alien artifact under the lunar surface (even more awesome). An investigative space mission is undertaken with the help of a self-aware murderous supercomputer named HAL 9000 (so fucking awesome we just peed a little bit).

The Predictions
Advanced Artificial Intelligence: The closest thing we had to HAL in 2001 were AOL Instant Messenger Bots, which can "chat" in an irritating, judgmental way. These bots were designed to function at an intelligence level on par with your average AOL user, so let's just say we weren't in immediate danger of a HAL-like consciousness taking over a NASA mission and eliminating its crew members. Luckily, our 2001-era highly-combustible space shuttles were quite capable of killing astronauts on their own, thank you very much.
Innovative New Technology: There's a scene in 2001 in which a character is dozing in front of a flat-panel screen built into the seat in front of him--an impressively accurate prediction of JetBlue and other airlines with TVs in their seat back. Even more noteworthy is that he's watching programming that's obviously from the 1960s, eerily anticipating Nick at Nite.
Widespread Space Travel: It's easy to chide Space Odyssey for its ambitious forecast of turn-of-the-century space travel, but keep in mind that the film was released in 1968, a full year before we faked the moon landing. Nobody could have guessed that the Soviet Union would forfeit the Space Race for fear of getting its dress dirty, and then finally collapse like a little girl. This deprived us the fruits of competition. Were the Soviets still tinkering around with satellites, we'd probably be colonizing Pluto instead of bitterly revoking its status as a planet.
Overall Accuracy
2001 is often celebrated for its clairvoyance, because a few of its inane predications came vaguely true. But, the major plot elements still seem like crackhead visions of the distant future. And the movie's notion that we'd still have attractive flight attendants in 2001 now seems preposterous.

Timecop (1994)

Set In 2004
The Premise
Jean-Claude Van Damme (played by Jean-Claude Van Damme) is a Time Enforcement Agent tasked with making sure people don't use time travel to dick around with the past.
The Predictions
Time Travel: Obviously we didn't actually have access to time travel in 2004. But, what sets Timecop apart is its asinine treatment of the subject. Timecop's major rule is that when you're traveling to the past, you can't come in direct contact with your past self because "the same matter cannot occupy the same space." Right, Timecop. We suppose it can't.
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