When you think of the greatest movie years of all time, one of the most recent entries people often turn to is 1999. A year that gave us some of the best of genre, independent, and blockbuster filmmaking.
Let’s take a look at some of the most essential movies of 1999.
The Sixth Sense
Often mistaken for a debut, the third feature film from auteur M. Night Shyamalan was such a smashing success upon release that it made him an instant cinematic cultural figure. The film’s iconic quotes are still spoken by audiences today, and the twist ending is difficult to outshine with its brilliance.
Beyond all of the elements that people speak about the most, the film remains a stunningly moving portrait of a family paralyzed by grief and mental illness. Haley Joel Osment’s performance as Cole Sear is one of the finest child performances of all time, and shows a character harnessing such a traumatizing curse and using it to spread as much good as possible. For as much as this one still gives us the shivers, it makes our eyes just as misty by the end.
Magnolia
‘Magnolia’Credit: New Line Cinema
Indie icon Paul Thomas Anderson released his third feature film, Magnolia, in the final weeks of 1999, and it’s the film that many fans of his still say defines his career, which is a tough placement to hold considering his other works.
The film functions in an anthology setting with each story becoming loosely connected by unexplained coincidences in the final act. It explores grief, hot-headedness, family, loneliness, and masculinity in a way that feels as if at any moment it will collapse under its own weight and ambition. However, due to the absolutely extraordinary script and direction by Anderson, and career–best performances from actors like Tom Cruise, the film flexes every muscle it has throughout every frame to deliver a truly unique experience upon every viewing. The score is whimsical, the thematics are dense and thoroughly explored, and like every iconic movie…it’s intensely quotable.
The Matrix
‘The Matrix’Credit: Warner Bros. Pictures
The Wachowski Sisters’ 1999 action epic spawned a wildly successful franchise, as well as one of the most iconic metaphors of all time. Both a deeply moving trans allegory, as well as a piece about being trapped in the modernity of existence, The Matrix revolutionized how action was written, choreographed, and filmed.
Taking keen inspiration from punk rock aesthetics and kung-fu style choreography, the film harnessed new-wave visual effects to create a cocktail of truly epic proportions. While the validity of the sequels is still up for debate amongst casual and hardcore fans, the first film is nearly universally agreed upon to be a landmark for action cinema, and one of the most important films of the 1990s.
Fight Club
‘Fight Club’Credit: Walt Disney Studios
If you’re searching for a film that has stood the test of time, especially with younger audiences, look no further than David Fincher’s Fight Club. For the past 27 years, the film has consistently cemented itself as a staple among men in their early-twenties, in particular, for its dissection of mental health issues and toxic masculinity.
While there is a conversation to be had about whether or not certain fans of the film have absorbed the messaging in the proper manner, the commentary itself still contains a great deal of substance.
Edward Norton and Brad Pitt’s dysfunctional relationship lays the groundwork for a deeply disturbing film about deeply disturbed people. Helena Bonham Carter turns in some of her best work in the film, and beyond the iconic twist ending that still turns heads today, the final sequence of the film remains one constantly referenced and parodied in media to this day.
Toy Story 2
‘Toy Story 2’Credit: Walt Disney Studios
What’s almost more fascinating than the actual film of Toy Story 2 is its making-of story. It was originally only greenlit to be a 60-minute, low-budget, straight-to-video release in a similar vein to the Aladdin sequels. However, after being impressed with the film’s reels, Disney executives greenlit production on a full, theatrically releasable film.
The sequel to the 1995 classic was a massive success, earning just as much as the original film in revenue, and became, at the time, the third-highest-grossing animated film of all time, right behind The Lion King and Aladdin.
The film itself is still sensational. The addition of characters like Jessie and Bullseye was hugely integral to the lore and thematics of the overarching story. The thematics themselves are more mature and explored with greater depth; the conflict is more high-stakes, and the characters reckon with themselves and their own mortality far more than anyone likely could have imagined…at least until the third film came out.
Honorable Mentions
These are further landmark films of the year, and should absolutely be considered among the rest of the bunch.
- The Blair Witch Project
- Being John Malkovich
- Election
- The Mummy
- Eyes Wide Shut
- American Beauty
- The Talented Mr. Ripley
- The Virgin Suicides
- The Green Mile
- 10 Things I Hate About You
- Star Wars: Episode I - The Phantom Menace
- Dogma
- Girl, Interrupted
