The Best Movie Of Each Year From 1925-2025

Honourable Mentions: The Insider, The Iron Giant, The Talented Mr. Ripley

1999 proved to be the perfect closing statement on a superb filmmaking decade, providing a rich mix of era-defining blockbusters like Stephen Sommers' The Mummy and indie phenomenons like The Blair Witch Project. In and amongst that offering included rich masterworks like Michael Mann's The Insider (a legitimate contender for the director's best), Brad Bird's The Iron Giant (which upsettingly tanked at the box office), and The Talented Mr. Ripley (a fantastic retelling of Patricia Highsmith's novel with a brilliant ensemble leading the way).

But given the transformation blockbuster cinema undertook in the nineties, it's perhaps no surprise that the best film of 1999 is arguably the most influential of the lot: the Wachowski Sisters' gravity-defying sci-fi odyssey, The Matrix.

A game-changer for action cinema, genre aesthetics, and even alternative fashion (thank you for your service, Kym Barrett), The Matrix remains a touchstone of nineties filmmaking and one whose stature has never diminished, even with endless imitations and parodies. It's a technical and textual tour de force, no matter your mileage with its sequels.