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Portal, GLaDOS and the comedy of machine villains

Why the funniest AI characters are also the most unsettling.

vinznsk · Sep 11, 2026 · 2 min read

Stories about artificial intelligence are older than computers. They have always been less about machines than about us: our fears of being replaced, our hopes of being understood, our questions about what makes a person.

The best works in this list do not try to predict the future. They take one idea seriously and follow it to an emotional conclusion, which is often more revealing than any forecast.

Our picks

Creators are also using AI as a tool, not just a subject. That raises its own questions about credit, payment and what we value in a work of art.

  • Best for a first introduction
  • Best for younger audiences
  • The classic everyone cites
  • Best for a long weekend

What it gets wrong

If you only have one evening, start with the first pick. If you have a weekend, work through the list in order; each one builds on the ideas of the last.

The question of whether a computer can think is no more interesting than the question of whether a submarine can swim.

Edsger W. Dijkstra

We will keep this list updated as new works arrive. Tell us what we missed; reader suggestions have shaped many of our past lists.

If you liked this

Critics have long argued about whether science fiction shapes technology or simply reflects it. The honest answer is probably both, and these works are a good place to see that in action.

We chose works that are easy to find on major platforms or in libraries. Availability changes by country, so check your local services.

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