The year 1999 saw the release of some incredible movies. Some of these are still popular in film discussions today, continuing to impress for various reasons and having an enduring legacy that lives on through loyal fans.
Users of the site Ranker have given votes for what they identify as the best movies of 1999. From a game-changing science fiction title about a simulated reality to an iconic romantic comedy based on one of the works of William Shakespeare, 1999 introduced many films that have stood the test of time and remain beloved to this day.
Payback
Not available to stream or rent.
Payback is about a thief named Porter who is betrayed when his wife and former partner take money from him and attempt to kill him. The movie follows Porter as he tries to track down the money and those who turned against him.
Payback offers a thrilling ride through Porter's journey that leaves many audience members eager for the next scene. Additionally, with well-executed action sequences, it is a film that fans of the crime genre will likely enjoy.
The Matrix
Available to stream on HBO Max.
In 1999, the Wachowskis wrote and directed a film that would become a cultural phenomenon: The Matrix. The movie centers on a man who is made aware that he is in a simulated reality, and after escaping, he joins a rebellion against the machines that hold humanity in this simulation.
The film includes some of the most recognizable roles so far for actors like Keanu Reeves, Carrie-Anne Moss, and Laurence Fishburne, all of whom help to make the film as iconic as it is. The Matrix has endured as one of the best sci-fi war movies of all time, cementing itself as an unforgettable entry in the genre and spawning several sequels, the most recent of which, The Matrix Resurrections, came out in 2021.
Galaxy Quest
Available to stream on Starz.
Galaxy Quest is a loving parody of films like those in the Star Trek franchise and of the fandom surrounding them, and it has endured for decades on its own merits as well. The movie is about the former cast of a television show called Galaxy Quest that receives contact from aliens known as Thermians, who believe the series to be real-life. The cast joins the effort to save the Thermians from an evil warlord.
Known for its hilarious characters and absurd plot, Galaxy Quest remains a favorite among many fans of the science fiction films to which it pays homage.
Fight Club
Available to stream on IMDb TV and rent on Apple iTunes.
Fight Club surrounds an unnamed narrator who, discontent with his current existence, helps to create a club in which men fight each other in an attempt to feel alive. This lifestyle ends up having unforeseen consequences that are more dangerous than the narrator had anticipated.
The film's themes have been discussed and studied heavily in the years since its release. With some of the most perfectly cast roles in a David Fincher movie like Brad Pitt as Tyler Durden, Fight Club offers phenomenal performances from a cast that has excellent chemistry.
Cruel Intentions
Available to stream on IMDb TV and rent on Amazon Prime Video.
Cruel Intentions is based on the novel Les Liaisons dangereuses by Pierre Choderlos de Laclos, but the time is modernized and the location is changed to New York City. The story follows a bet that takes place between two siblings, which challenges the latter to seduce their new classmate, who has expressed that she wants to wait until marriage.
The performances of Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair have garnered extensive attention and remain some of their most highly regarded portrayals. The film was so popular it even inspired a musical adaptationthat debuted in 2015.
The Green Mile
Available to rent on Apple iTunes and Amazon Prime Video.
Often considered one of the best '90s movies in general, The Green Mile offers elements that move audiences in ways that not many films can. It focuses on Paul Edgecomb, an officer who works on death row when John Coffey arrives. John has the power to heal others, and he displays extensive kindness toward others, leading Paul to question if he truly is guilty of the crimes of which he has been convicted.
Heartfelt and heartbreaking performances from Michael Clarke Duncan and Tom Hanks help to elevate a film that has left many people in tears.
The Mummy
Available to stream on HBO Max.
Starring Brendan Fraser and Rachel Weisz in some of their most famous roles to date as Rick O'Connell and Evelyn Carnahan, respectively, The Mummy has entertained movie lovers for decades and has become a classic for many fans. A remake of a 1932 film, it follows a group of adventurers who must stop a cursed mummy whom they accidentally awakened.
Fun and full of action, The Mummy continues to impress new audience members and has spawned various additions to the series, though the 1999 film tends to be the most beloved.
10 Things I Hate About You
Available to stream on Disney+.
An interpretation of William Shakespeare's The Taming of the Shrew, 10 Things I Hate About You is among the favorites of many fans of romantic comedies. It centers on Cameron, a high school student who wants to date Bianca, but the latter's father does not permit her to date until her older sister Kat dates. Cameron tries to pay another student named Patrick to date Kat, which leads to a host of romantic drama.
Featuring memorable scenes like Heath Ledger singing "Can't Take My Eyes Off You" alongside a marching band, 10 Things I Hate About You continues to tug at fans' heartstrings to this day.
The Sixth Sense
Available to rent on Apple iTunes and Amazon Prime Video.
The Sixth Sense follows Dr. Malcolm Crowe, a child psychologist who begins to work with Cole Sear, a young boy who claims to be able to see ghosts. The film features many mysterious elements and culminates in perhaps one of the most famous movie endings of the 1990s.
As one of M. Night Shyamalan's most highly regarded works, The Sixth Sense contains some of Shymalan's best-written characters, including Cole and Malcolm, who are excellently portrayed excellently by Haley Joel Osment and Bruce Willis, respectively.
Office Space
Available to rent on Apple iTunes and Amazon Prime Video.
Written and directed by Mike Judge, Office Space is based partly upon Judge's Milton cartoon shorts. The film focuses on Peter, a dissatisfied programmer who undergoes hypnotherapy and becomes incredibly relaxed. However, the hypnotherapist dies without snapping Peter out of this state, leading him to go through his days with a new outlook on life.
Widely recognized for some of its iconic scenes, Office Space has become a cult classic with genuinely hilarious elements that keep audiences entertained for its entire runtime.