The 2000 Best Dramatic Presentation Hugo was presented September 3, 2000 at Chicon 2000.
- Galaxy Quest (1999) [DreamWorks SKG] Screenplay by David Howard and Robert Gordon; Story by David Howard; Directed by Dean Parisot
- The Matrix (1999) [Silver] Written by Andy Wachowski & Larry Wachowski; Directed by Andy Wachowski and Larry Wachowski
- The Sixth Sense (1999) [Hollywood/Spyglass/Kennedy/Marshall] Written by M. Night Shyamalan; Directed by M. Night Shyamalan
- Being John Malkovich (1999) [Gramercy/Propaganda/Single Cell] Written by Charlie Kaufmann; Directed by Spike Jonze
- The Iron Giant (1999) [Warner Brothers] Screenplay by Tim McCanlies; Screen Story by Brad Bird; Directed by Brad Bird; based on the book The Iron Man by Ted Hughes
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