The 15 Best Movies of 1999, from ‘Magnolia’ to ‘The Matrix’

1999 was a prolific year for movies. As the world was preparing to turn ahead to the new millennium (or for the end of civilization as we thought we knew it), culture was flourishing thanks in part to movie releases from many of the great filmmakers to ever live, as well as some up-and-coming auteurs ready to make a name for themselves. This pinnacle year for the film industry spanned the globe as international filmmakers from different backgrounds, ethnicities, and life experiences helped usher in many noteworthy foreign language pictures destined to live on for years to come.

best movies of 1999
The Best Movies of 1999, including The Matrix

And at the time of writing this, we’ve managed to survive 25 years since that groundbreaking year. The depth of movie releases in 1999 is what is quite striking. We’re highlighting the 15 best movies of 1999 in this article, but there are dozens of film releases worth recognizing. There are deep cuts from acclaimed directors like Paul Schrader, Steven Soderbergh, Alexander Payne, and Martin Scorsese that won’t make this list today, but are obviously worth seeing for a handful of reasons.

And that speaks more to the quality of this year than the quality of those movies. Films like The Limey or Bringing Out the Dead would surely make many year-end lists for most years since 1999 if they had a different release date, but they’re buried in a list of expansive, indulgent, and simply remarkable pictures that still live on today in many ways.

I may revisit this down the line as I’ve seen more and more and add to it, but for now, here are the 15 best movies of 1999:

15. Being John Malkovich

being john malkovich movie 1999

14. Audition

audition movie 1999

13. Magnolia

magnolia

Magnolia might feel a bit like the film that got away from Paul Thomas Anderson (because it kinda is), but it’s the sort of big-budget passion project that up-and-coming filmmakers rarely get to make nowadays. The ensemble cast of Magnolia is littered with A-listers and common Paul Thomas Anderson players, from Julianne Moore and Philip Seymour Hoffman to Tom Cruise and John C. Reilly, each actor adds their own weight to this shotgun blast of characters. Magnolia movie review

12. The Straight Story

the straight story

The Straight Story veers off from the usual David Lynch motifs and expectations, but it delivers strong emotional highpoints and a sturdy story nevertheless. The director of classics like Mulholland Drive and Blue Velvet proves he can work at different speeds, and this straight to Disney family story is told with poignant intelligence that many of its contemporaries aren’t. The Straight Story movie review

11. Fight Club

Fight Club

Released over two decades ago, David Fincher’s Fight Club remains in popular culture the way few films ever do. A movie that often resonates with those feeling marginalized by society, Fight Club lives on for each generation to interpret in new ways. Fight Club movie review

10. The Green Mile

the green mile movie 1999

9. The Sixth Sense

the sixth sense movie 1999

8. Ghost Dog: The Way of the Samurai

ghost dog movie 1999

7. Beau Travail

beau travail movie 1999

6. Toy Story 2

toy story 2 movie 1999

5. The Blair Witch Project

the blair witch project movie 1999

4. The Matrix

the matrix movie 1999

3. The Virgin Suicides

the virgin suicides

2. The Insider

the insider movie 1999

1. Eyes Wide Shut

eyes wide shut movie 1999

READ MORE: 1999 Archive

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