The Best Movie Of Each Year From 1925-2025

27. 1999 - The Matrix

The Matrix
Warner Bros.

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.

 
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WhatCulture's very own resident movie guy, Ewan has been working in the content creation biz for over 10 years now, having started as a freelance contributor to WhatCulture Gaming all the way back in 2015. After graduating with a First-Class Honours in History from Northumbria University in 2017 (where he won a prize for a totally killer dissertation on the Watergate years), Ewan took on the role of Comics Editor at WhatCulture and quickly developed WhatCulture Comics into one of the biggest superhero-focused channels on YouTube. He followed this with a brief hiatus at Screen Rant in 2021, where he worked across the Gaming and Film sections as a writer and editor, before returning to WhatCulture as a Senior Content Producer / Presenter in 2023. He started his own podcast, We Love Dad Movies, in 2022, and has contributed several written pieces to the Eisner-nominated comics website Shelfdust as well. In his current role, Ewan incorporates his love of cinema, comic books, and history into written pieces and video essays for WhatCulture's Film & TV channel, as well as WhatCulture Gaming and WhatCulture Horror, with a particular focus on nineties-era Dad Movies, old school Westerns, and Golden Age Hollywood Noir. John Carpenter is his fave, and he thinks Batman Beyond should never have been cancelled. If that's your vibe, you'll probably like his stuff.