The Matrix (1999)

Perhaps the coolest movie of the 1990s, this cyberpunk mind boggler by the Wachowskis imagines a world in which what human beings think of as real is actually “the Matrix,” an elaborately realistic form of Virtual Reality—their lives are basically dreams. Enter Neo (Keanu Reeves), a computer programmer who’s trained to see through all this and bring it down. Like so many of the best films about man’s relationship to machines, the movie is a triumph of style. You can just groove on everything from Neo’s long black coat to the sequences when time seems to freeze and the camera wanders among suspended bullets.

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2046 (2004)

Wong Kar Wai’s operatic film follows the exploits of a womanizing writer (Tony Leung Chiu-wai) in 1960s Hong Kong who has been wounded in love. Projecting his amorous unhappiness into the future, he writes a story set in 2046 Hong Kong, a brightly hued but cold city where his hero is trapped on a train and falls in love with one of the beautiful androids who work on it. Boasting the fantastic costumes you expect from Wong and his designer William Chang Suk-ping, this is a movie that reminds us that, when we see a movie about our future relationship to machines, what we’re actually seeing are today’s dreams and desires.

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Her (2013)

In Spike Jonze’s wonderful piece of comic melancholy (or maybe melancholic comedy), Joaquin Phoenix plays Theodore, a lonely professional letter-writer in a future L.A. who gets a computer operating system with artificial intelligence and proceeds to name it Samantha. Almost predictably he starts to fall in love—heck, she’s voiced by Scarlett Johansson—but there’s one huge problem: AI is a whole lot smarter than human intelligence. (You find something of the same idea in Ex Machina, where the OS operates a body played by Alicia Vikander.) Samantha isn’t sinister like Alpha 60 or HAL, which in a way makes her scarier because Theodore can feel so warmly toward her that he forgets that she’s actually a “her.”