The 25 Movies That Will Make You Want to Party Like It’s 1999

From mind-bending science fiction to heartbreaking teen romances, thought-provoking dramas, and funny comedies, 1999 was a year of cinematic greatness that still resonates today. Here are 25 of the best films from that year. Do you agree?

1. The Mummy (1999)

The Mummy 1999
Image Credit: Universal Pictures.

Fun for all audiences, The Mummy is equal parts action, comedy, and the spooky. In the movie, Brendan Fraser and Rachel Weisz play explorers who accidentally wake up an old Egyptian mummy and must stop it from causing worldwide chaos. The Mummy captures the spirit of ’90s adventure movies with its fast-paced action scenes and swashbuckling fun.

2. Galaxy Quest (1999)

Galaxy Quest 1999
Image Credit: DreamWorks Pictures.

Galaxy Quest is a funny science fiction comedy that makes fun of the rules of classic space operas like Star Trek. Tim Allen, Sigourney Weaver, and Alan Rickman all-star in the movie, which is about a group of actors from a canceled space-themed TV show who are confused by an alien race for real space heroes. The film captures the fun side of ’90s movies with its witty humor and has become a cult classic today.

3. Fight Club (1999)

Fight Club 1999
Image Credit: 20th Century Fox.

Speaking of cult classics, David Fincher’s Fight Club is a thought-provoking and challenging movie exploring themes of consumerism and identity. It’s about an office worker who can’t sleep and starts a secret fight club as a way to rebel, and stars Edward Norton and Brad Pitt. The edgy and provocative plot of the movie made it a fan favorite and one of the most influential movies of the 1990s.

4. Office Space (1999)

Office Space 1999 Milton
Image Credit: 20th Century Fox.

“Have you seen my stapler?” Anyone who has ever worked a 9-to-5 office job will find Office Space to be an instantly relatable and amusing comedy. It follows a group of office workers who decide to fight against their soul-crushing work environment. Office Space shows what it was like to work in an office in the 1990s and what it was like to fight against it. It does this with witty satire and memorable characters.

5. Arlington Road (1999)

Arlington Road 1999
Image Credit: Screen Gems.

The psychological movie Arlington Road keeps people on the edge of their seats. The movie, which stars Jeff Bridges and Tim Robbins, is about a college professor who starts to think that his new neighbors are involved in domestic terrorism. The tense and suspicious mood of the movie is like the thrillers of the late 1990s.

6. The Matrix (1999)

The Matrix 1999 Neo and Trinity
Image Credit: Warner Bros. Pictures.

The Matrix is a groundbreaking science fiction action movie starring Keanu Reeves, Laurence Fishburne, and Carrie-Anne Moss. It explores the idea of a machine-controlled simulated world. The Matrix became an instant classic and one of the most influential movies of the late 1990s because of its mind-bending visual effects and exciting action scenes.

7. American Beauty (1999)

American beauty 1999
Image Credit: DreamWorks Pictures.

To explore the complexity of suburban living, American Beauty is a darkly humorous drama. The movie stars Kevin Spacey and is about how a middle-aged man’s life falls apart when he falls in love with his daughter’s friend. This movie won the Academy Award for Best Picture. Critics praised it for its biting humor and look at existential crises.

8. The Green Mile (1999)

The Green Mile
Image Credit: Universal Pictures.

Frank Darabont’s thriller The Green Mile is full of heart and strong feelings. The film stars Tom Hanks and Michael Clarke Duncan and is about a jail guard on death row who meets a prisoner with special skills. In 1999, people were moved by how the movie dealt with themes like justice, forgiveness, and the supernatural.

9. Magnolia (1999)

Magnolia 1999
Image Credit: New Line Cinema.

Paul Thomas Anderson’s Magnolia is a big, ambitious story with a big cast. The movie has a great cast, including Tom Cruise, Julianne Moore, and Philip Seymour Hoffman. It is set in the San Fernando Valley and tells several linked stories. Magnolia is a great example of how well movies were made in the 1990s because of its complex plot and strong emotions.

10. Election (1999)

Election 1999
Image Credit: Paramount Pictures.

Election is a comedy with a dark sense of humor, starring stars Reese Witherspoon and Matthew Broderick. The film demonstrates how tough high school politics can be through the eyes of a determined student running for class president. Election is a great comedy from 1999. It has sharp humor and smart things to say about desire and ethics.

11. Eyes Wide Shut (1999)

Eyes Wide Shut 1999 Nicole Kidman
Image Credit: Warner Bros.

In the enigmatic and provocative thriller Eyes Wide Shut, directed by Stanley Kubrick and featuring Tom Cruise and Nicole Kidman, secrets unravel in mysterious ways. The movie looks at sexual desire and jealousy through the eyes of a married couple whose relationship is tested by a secret society and several sexual encounters. Kubrick’s careful direction and the mysterious mood of the movie make it an interesting and controversial piece of art.

12. The Sixth Sense (1999)

The Sixth Sense 1999
Image Credit: Buena Vista Pictures.

The Sixth Sense supernatural movie stars Bruce Willis and Haley Joel Osment. M. Night Shyamalan directed it, and it’s still his best to date. It follows a young boy who says he can see and talk to the dead. In 1999, The Sixth Sense became a cultural phenomenon thanks to its famous twist ending and suspenseful story. 

13. Being John Malkovich (1999)

Being John Malkovich
Image Credit: Universal Pictures.

Being John Malkovich is strange and full of new ideas. It follows a magician who finds a way into the mind of actor John Malkovich. It stars John Cusack, Cameron Diaz, and John Malkovich as himself. With its strange plot and witty dialogue, the movie is a great example of the weirdness of the 1990s.

14. Toy Story 2 (1999)

Toy Story 2 1999
Image Credit: Walt Disney Pictures and Pixar Animation Studios.

Toy Story 2 is a popular cartoon movie that continues the story of the groundbreaking Toy Story. The film reunites Woody, Buzz Lightyear, and the entire cast of Andy’s Toys for yet another captivating adventure. Toy Story 2 kept up the success of its predecessor with a heartwarming story, memorable characters, and great animation. It is still a beloved classic from the 1990s.

15. Star Wars: Episode I – The Phantom Menace (1999)

The Phantom Menace 1999
Image Credit: Lucasfilm Ltd.

After a long break, Star Wars: Episode I – The Phantom Menace returned the popular Star Wars series to the big screen. It’s the prequel to the original Star Wars trilogy and tells the early stories of characters like Anakin Skywalker and Obi-Wan Kenobi. Despite mixed reviews, the movie was a big deal in 1999 and got people interested in the Star Wars world again.

16. The Boondock Saints (1999)

The Boondock Saints 1999
Image Credit: Twentieth Century Fox.

Troy Duffy’s cult action movie The Boondock Saints is a favorite among movie fans. The film is about two Irish-American brothers who decide to kill criminals in Boston alone. It became a cult favorite in the years after it came out because of its dark humor, stylized violence, and memorable characters.

17. The Wood (1999)

The Wood 1999
Image Credit: Paramount Pictures.

The Wood is a comedy-drama about a boy coming of age. The movie is about three childhood friends who meet up in their old neighborhood the night before one of them gets married. They talk about their past adventures and think about their relationships. 

18. Jawbreaker (1999)

Jawbreaker 1999
Image Credit: TriStar Pictures.

Jawbreaker is a dark comedy that Darren Stein is in charge of. The movie is about a group of high school friends who accidentally kill one of their own. It stars Rose McGowan, Rebecca Gayheart, and Julie Benz. Fans of ’90s teen movies love this movie because it mixes dark humor, comedy, and high school drama.

19. 10 Things I Hate About You (1999)

10 Things I Hate About You 1999
Image Credit: Touchstone Pictures.

Gil Junger’s movie 10 Things I Hate About You is a current take on Shakespeare’s The Taming of the Shrew. The film is a charming and funny high school love comedy with Heath Ledger, Julia Stiles, and Joseph Gordon-Levitt in the lead roles. It is still a popular teen favorite from the 1990s because the characters are easy to remember, and the dialogue is smart.

20. Superstar (1999)

Superstar 1999
Image Credit: Paramount Pictures.

The film Superstar is a comedy based on Molly Shannon’s Saturday Night Live character, Mary Katherine Gallagher. Mary Katherine wants to be a star at her high school talent show, and the movie shows how she tries to get there. Superstar gets the irreverent spirit of ’90s comedy with its quirky humor and Molly Shannon’s iconic performance.

21. Three Kings (1999)

Three Kings 1999
Image Credit: Warner Bros.

Three Kings is a comedic war movie with George Clooney, Mark Wahlberg, and Ice Cube in the lead roles. The movie is about a group of American soldiers going on a treasure hunt after the Gulf War. The story takes place during the war and is a unique take on the war movie genre because it has action, comedy, and social criticism.

22. Analyze This (1999)

Analyze This 1999
Image Credit: Warner Bros.

Analyze This features Robert De Niro and Billy Crystal and is about a neurotic mob boss who tries to get help from a therapist who doesn’t want to be involved in the shenanigans. Analyze This is hilarious and has many quotable lines. 

23. Deep Blue Sea (1999)

Deep Blue Sea 1999
Image Credit: Warner Bros.

Deep Blue Sea is a science fiction/horror movie and cult classic taking place in a lab where scientists experiment on sharks to find a fix for Alzheimer’s disease. However, things take a scary turn when the sharks become smart and dangerous. Deep Blue Sea is a thrilling creature movie with memorable lines and horrific shark scenes.

24. October Sky (1999)

October Sky 1999
Image Credit: Universal Pictures.

October Sky is an inspiring drama about a young boy’s dream of making rockets in a small coal-mining town. Jake Gyllenhaal and Chris Cooper play the main characters and tell a story that makes you feel good, with themes of drive and interest in science.

25. The Insider (1999)

The Insider 1999
Image Credit: Touchstone Pictures.

The truth takes center stage in the gripping drama The Insider, helmed by director Michael Mann and featuring powerhouse performances by Russell Crowe and Al Pacino. The movie is based on the true story of a worker in the tobacco business who blows the whistle on wrongdoing by the company. The Insider is a thought-provoking movie showing people’s interest in real-life crimes and investigations in the late 1990s. It has strong performances and looks at the ethics of journalism.

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Image Credit: Paramount Pictures.

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Only You
Image Credit: TriStar Pictures.

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Jaws Steven Spielberg
Image Credit: Universal Pictures.

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Trading Places
Image Credit: Paramount Pictures.

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What About Bob 1991
Image Credit: Tombstone Pictures.

The nineties were an incredible decade in film, including several classic comedies. Here are some of my favorites that are guaranteed to tickle your funny bone. Have you seen them?

Featured Image Credit: The Mummy – Universal Pictures. Galaxy Quest – DreamWorks Pictures. The Matrix – Warner Bros. Pictures.