15 Great Movies Turning 25 Years Old in 2024

As the passage of time continues to move on, more and more originally groundbreaking and brand-new experiences find themselves slowly being relegated to being classics of a bygone era. There’s absolutely nothing wrong with a movie not being brand new anymore, but it can always feel jarring to realize that a film you remember watching in theaters or as a kid is over 20 years old. This is especially apparent for films of the late 90s and early 2000s, which were released during the technological boom of the internet and the beginning of the digital era as we know it.

With the brand-new year of 2024 already off to an exciting start, the last of the films released in the 20th century will be celebrating their 25th-year anniversaries throughout the year. A lot of movies from this period were massively influential for film culture as a whole throughout the 21st century, and a number of them still hold up tremendously to this day. While it’s certainly still exciting to watch a brand-new 2024 release, it could also be a great time to reminisce back and celebrate the quarter-century anniversary of some of the greatest films of all time.

15 ‘The Talented Mr. Ripley’ (1999)

Release Date: December 12th, 1999

One of the most critically acclaimed crime dramas of the era, The Talented Mr. Ripley follows the story of Tom Ripley (played by Matt Damon), who wishes more than anything else that he could live another life. He soon realizes that he may have that chance, as after meeting an arrogant playboy named Dickie, Ripley creates a plan to lie and scheme his way into his inner circle and life. Now that he’s wormed his way into an upper-class world, Tom does everything that he can to steal Dickie’s life right from under his nose.

The Talented Mr. Ripley made a massive splash among critics and audiences upon its release, garnering multiple Academy Award nominations and continued praise ever since its release. The film features an all-star cast who all provide some of the highlights of their respective careers, especially the case of Jude Law, who became an icon thanks to this breakout role as Dickie. The themes and messages of The Talented Mr. Ripley are also still so poignant and powerful that they still strike a chord with audiences, continuously being regarded as a timeless viewing experience.

Watch on Paramount+

14 ‘All About My Mother’ (1999)

Release Date: November 24th, 1999

One of many masterful melodramas by Spanish filmmaker Pedro Almodóvar, All About My Mother follows the story of Manuela, a single mother living in Madrid who witnesses her only son die on his birthday. On top of being filled with grief and misery from her sudden loss, she finds herself traveling back to Barcelona to tell the boy’s father about the death of his son. However, the father in question never even knew that his son existed in the first place.

Almodóvar has always had an uncanny ability to weave together powerfully emotional films throughout his extensive career, with All About My Mother arguably being his most iconic film to date. Despite the tragedy at the center of it all, the film is a surprisingly effective comedy, with a great number of heartfelt moments that make the entire experience that much more memorable and enjoyable. Complete with spectacular visuals and triumphant performances, the film cements a strange legacy as one of the premiere movies to watch on Mother’s Day.

Rent on Amazon Prime

13 ‘The Virgin Suicides’ (1999)

World Premiere: May 19th, 1999

The feature-length debut of female director icon Sofia Coppola, The Virgin Suicides follows the story of the mysterious Libson sisters, who have lived their entire lives sheltered by their strict, religious parents. When a group of teenage boys finds an acute interest in the mysteries surrounding the sisters, they unknowingly put themselves in a terrifyingly unexpected series of events with life-threatening consequences.

While Sofia Coppola would continue to develop and delve into the themes of femininity, youth, fame, and alienation throughout her career, all of these major facets can find their origin in The Virgin Suicides. Even to this day, the film resonates powerfully thanks to its poignant and timeless themes, as well as messaging that continues to stay relevant and powerful year after year. Few films have been able to continuously enchant and enthrall audiences well after its release, helping The Virgin Suicides cement a legacy as one of Sofia Coppola’s most prominent masterpieces.

Watch on Fubo

12 ‘Toy Story 2’ (1999)

Release Date: November 24th, 1999

The legendary sequel to one of the most beloved animated movies of all time, Toy Story 2 continues the story of Woody and Buzz, having been left to their own devices while Andy is off at Cowboy Camp. However, when an obsessive toy collector kidnaps Woody, the rest of Andy’s toys band together on a high-stakes rescue mission to save him. But Woody’s new residence seems to be far from a prison at all and is instead a place that fully worships and loves the gravitas of him as a collector’s item, making it a difficult choice about whether to stay or to return home to Andy.

While the original Toy Story was a technical marvel and revolution when it came to computer animation in film, Toy Story 2 managed to up the ante in nearly every conceivable way from the first film. From improved animation quality and more frequent comedic moments to higher stakes and a genuine development and evolution of the world, Toy Story 2 does as good a job as a sequel can achieve. Toy Story 2 is one of the very few sequels out there that not only lives up to the insurmountable high legacy of the original but in some instances finds ways to surpass the untouchable original.

Watch on Disney+

11 ‘Eyes Wide Shut’ (1999)

Release Date: July 16th, 1999

The final film by legendary filmmaker Stanley Kubrick, Eyes Wide Shut follows the story of Dr Bill Harford (played by Tom Cruise) who undergoes a sexual awakening after his wife admits to having sexual fantasies with someone she met. This awakening and obsession with having a similar sexual encounter leads to him discovering an underground sexual group, and he decides to attend one of their meetings. Once there, however, he soon realizes that he is in well over his head, and will have to parse his way through all the strange and confusing procedures.

As is the case with many of Kubrick’s other films, Eyes Wide Shut is a multifaceted and multilayered masterpiece that has been examined and dissected since its release, with no two viewings feeling the same. The film creates drama and suspense in a way that very few films can accomplish, keeping its stakes and tension high while leaving room for mystery and suspense throughout. It’s a genuine marvel that the film achieved such massive highs as it did, considering the massive nightmare that it took to create the film behind the scenes.

Rent on AppleTV+

10 ‘The Iron Giant’ (1999)

Release Date: August 6th, 1999

One of the last truly great 2D animated movies of the 20th century, The Iron Giant follows the story of the unexpected friendship that blossoms between a nine-year-old boy and a giant metal robot from outer space. However, despite the kindhearted nature of the giant that the boy sees within him, the rest of the world is terrified, seeing him as nothing more than a destructive weapon and a threat to civilization. It soon becomes up to the boy to do what he can to keep the giant hidden, so as not to sound the alarms and have him possibly taken away or taken apart.

Despite its initial box office bombing, The Iron Giant has grown to have a powerful legacy as one of the most emotionally palpable and strongest animated films of its era. The film seamlessly combines 2D animation with computer-animated 3D to create an amazing story of friendship and heartbreak that has greatly stood the test of time. While many box office bombs are simply forgotten in the sands of time, The Iron Giant is definitive proof that pure quality and heart are the ultimate deciding factor in what film becomes a bonafide classic.

Rent on Amazon Prime

9 ‘The Blair Witch Project’ (1999)

Release Date: July 14th, 1999

One of the biggest defining horror phenomenons of the era, The Blair Witch Project ushered in a new wave of found footage horror films as well as low-budget films attempting to recapture the magic and success. The film follows the story of three student filmmakers in October 1994, who disappear in the woods while shooting a documentary. The footage of the film is presented as the remaining recovered footage from the students, depicting their last days before their mysterious and terrifying demise.

Those who were around during the height of The Blair Witch Project‘s popularity in the lead-up to its release understand just how much of a cultural phenomenon the film became. It was the first of its kind in terms of films that used the internet for its genius marketing campaign and redefined what was considered possible in terms of low-budget filmmaking, a testament to what was possible in the digital era. While many other horror movies have taken the found footage concept and built upon and expanded what The Blair Witch Project popularized, the undeniable legacy of the original cannot be denied.

Watch on The Criterion Channel

8 ‘The Mummy’ (1999)

Release Date: May 7th, 1999

The action-adventure remake of the classic Universal horror monster film, The Mummy follows adventurer extraordinaire Rick O’Connell as he and his team uncover hidden ruins in 1920s Egypt. They unknowingly end up unleashing a deadly cursed mummy, the former High Priest Imhotep, who has been cast away and suffering in the ruins for over three thousand years. Now that he has been reawakened, he begins to enact his curses upon the world, leaving it up to O’Connell to put a stop to the mummy and save the world.

While many action-adventure blockbusters of the 90s and 2000s find themselves aging poorly or being too cheesy on a rewatch, The Mummy strikes a perfect balance that makes it infinitely rewatchable. Thanks to the impressive special effects that at points still hold up today as well as the enthralling and electric lead performance from Brendan Fraser, The Mummy is a blast of a good time and one of the best blockbusters of the era.

Rent on Amazon Prime

7 ‘Office Space’ (1999)

Release Date: February 19th, 1999

One of the most well-regarded cult classic comedies of the 90s, Office Space follows the story of three office workers, Peter, Michael, and Samir, who are sick of their and form a scheme to get their revenge. As payback for the job continuously sapping away at their lives for years, they plan to slowly embezzle and steal money from the company cents at a time, so that they never have to worry about money again. However, the plan proves itself to be more difficult than imagined, having to balance around their quirky coworkers and unbearable bosses.

Comedy movies always have the greatest potential out of any genre to become underground hidden gems that acquire cult followings over the years with their signature forms of comedy. Office Space is no different, as its dry and cynical reflection of the pains and struggles of the 9 to 5 office life rung themselves to be more and more funny to audiences as the years went on. Combined with numerous iconic moments, messages, and themes that still hold up to this day, Office Space continues to deliver as one of the standout comedies of its era.

Watch on Max

6 ‘Magnolia’ (1999)

Release Date: December 17th, 1999

One of the earliest films by filmmaker legend Paul Thomas Anderson, Magnolia paints a portrait of the San Fernando Valley, following the stories of a variety of different characters on their own personal journeys. While each story appears to be disconnected from one another, they each find a way to intersect and collide with one another in different ways, as life finds a way to make sense of the chaos by the end.

While Anderson has had numerous other iconic films in his career since Magnolia, such as There Will Be Blood, Phantom Thread, and Licorice Pizza, Magnolia still stands out as one of his finest cinematic works. The way that the film seamlessly blends and weaves together its contrasting stories into a singular cohesive narrative is a work of mastery upon itself, even before considering the film’s multitude of other successes. The film is the highlight of a number of its stars’ careers, including the likes of Tom Cruise, John C. Reilly, and William H. Macy.

Rent on Amazon Prime

5 ‘The Sixth Sense’ (1999)

Release Date: August 6th, 1999

The cinematic masterpiece that put M. Night Shyamalan on the map, The Sixth Sense follows the story of the connection between psychologist Malcolm Crowe and nine-year-old boy Cole Sear. After witnessing an unexpected tragedy, Cole has seemingly adopted the ability to see the ghosts of deceased people as a part of his daily life, and they ask him to do terrible deeds. It soon becomes up to Malcolm to not only get to the bottom of the mystery behind Cole’s newfound ability, but to keep him safe from these dangerous spirits.

The Sixth Sense was a massive hit on its release, providing a thrilling and terrifying story that revolutionized what was considered possible for mystery thrillers and horror films in general. The film features notable amazing performances from Bruce Willis and Haley Joel Osment, as well as having one of the most iconic and powerful twists in film history. While Shyamalan’s career has certainly had its ups and downs over the years, it’s hard to deny that The Sixth Sense is his highest crowning achievement as a thriller director.

Rent on Amazon Prime

4 ’10 Things I Hate About You’ (1999)

Release Date: March 31st, 1999

Adapted from William Shakespeare‘s The Taming of the Shrew, 10 Things I Hate About You is a teen romantic comedy that translates the story to a modern high school setting. The film follows Cameron, who in an attempt to go on a date with Bianca, enlists the help of bad boy Patrick, having him begin dating Bianca’s older sister Kat so that Bianca can begin dating as well. However, their plan begins to face several obstacles, from other students looking to date Bianca to Kat catching onto Cameron and Patrick’s scheme.

The late 90s and early 2000s were a premiere time when it came to teen movies and romantic comedies, with 10 Things I Hate About You being one of the best instances of both genres of the period. The chemistry and dynamic between Heath Ledger and Julia Styles works tremendously well, alongside numerous comedic sequences and moments that have cemented a powerful legacy for the film.

Watch on Disney+

3 ‘Being John Malkovich’ (1999)

Release Date: October 29th, 1999

A wild psychological comedy by director Spike Jonze and writer Charlie Kaufman, Being John Malkovich follows the story of Craig, a puppeteer living a boring dead-end office job. However, his life is suddenly spiced up when he discovers a mysterious tunnel in his office that happens to be a portal into the head of John Malkovich. It doesn’t take long before the portal becomes the talk of the town, with everyone who experiences it having their life changed forever, with the news of the portal’s existence soon reaching Malkovich himself.

Kaufman’s stories have always had the tendency to use abstract and strange concepts as a jumping-off point for powerful philosophical themes and underlying messages. Being John Malkovich is easily the greatest example of this, with its high-concept premise allowing for great deals of comedy as well as existential fear and anxiety on a level simply unparalleled in filmmaking. The film’s powerful usage of magical realism creates a strange and enthralling world that audiences can’t help but fall in love with as time goes on, and the film continues to age beautifully and gracefully.

Rent on Amazon Prime

2 ‘The Matrix’ (1999)

Release Date: March 30th, 1999

One of the most influential and groundbreaking sci-fi films of the digital era, The Matrix brought new life into the sci-fi genre at a time when the genre was fluctuating and becoming repetitive. The film takes place in a far-off future, where the world and humanity have been overtaken and controlled by robotic overlords, with humans being placed in a simulation of the real world while their bodies are used as batteries. However, there is an underground group consisting of the last of humanity attempting to fight back, as computer hacker Neo joins the battle and escapes the simulation.

Getting inspiration from ’80s and ’90s anime, The Matrix‘s flashy visuals and abstract concept completely revolutionized what was considered possible for both sci-fi films and action blockbusters as a whole. The world and characters created in The Matrix are filled with creative possibilities, being left open-ended enough to make it a massive hit that rivaled the sci-fi franchises of old. While the eventual sequels would fail to live up to the strength of the original film, the first entry in the franchise still holds a special place in the hearts of many.

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1 ‘Fight Club’ (1999)

Release Date: October 15th, 1999

One of the most iconic and recognizable films of the 90s, Fight Club follows the story of a rag-tag partnership between an insomniac and a soap salesman, who begin letting their aggression loose on each other in hand-to-hand combat. Their unexpected “fight clubs” begin to pick up traction, with larger and larger groups of people looking to release their tension in this way nearly everywhere they go. However, as things get out of control, Tyler Durden begins to enact a dangerous out-of-control plan to put an end to the monotony of modern life once and for all.

Fight Club was once considered one of, if not the most iconic films of the digital era, with its aggressively powerful underlying themes that went over the heads of many audiences alongside flashy visuals and powerful lead performances. Even 25 years after its release, its true meaning and themes are still a point of constant conversation, as the film is frequently considered by some to be one of the greatest movies of all time.

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