20 Great Movies Celebrating 25 Years in 2023

The year 1999 gets a lot of credit for being a great movie year. On its 20th anniversary in 2019, myriad pieces were written about how 1999 was one of the best years for film ever, an iconic year, etc. But much of that conversation ignores how fantastic the previous year was.

But 1998, which celebrates its 25th anniversary this year, was a fantastic year in film itself. It gave us cult classics, debuts from directors who would go on to be stars, career high points for established directors, and more.

Let’s look back at 20 of the best movies turning 25 this year. It’s a wide swath, so there’s something for every mood, and every audience, whether you’re watching with the kids or looking for something children shouldn’t be near.

The Big Lebowski

The Big Lebowski 1998
Photo Credit: Working Title Films

Despite their many Oscar wins, the Coen brothers may be best remembered for this neo-noir comedy about a lazy man caught up in an equally complicated and stupid mystery. The Big Lebowski is such a cult classic that there’s even an entire religion based around it and Jeff Bridges’ iconic performance as The Dude. Whether you’re a practicing “Dudeist” or have never seen it, The Big Lebowski is a delight.

The Thin Red Line

thin red line
Image Credit: 20th Century Fox

The Thin Red Line marked Terrence Malick’s return from a two-decade filmmaking hiatus. The film is an alternately beautiful and harrowing adaptation of the novel of the same name by James Jones that highlights Malick’s talent for weaving together images of nature and humanity’s cruelty. It’s one of the best war movies ever made and undoubtedly one of the most unique.

Velvet Goldmine

Velvet Goldmine
Image Credit: Miramax

Todd Haynes’ Velvet Goldmine is a fictional biopic about Brian Slade (Jonathan Rhys Meyers), a character based on David Bowie. It’s a delightful ride through the history of glam rock with outstanding costumes, beautiful faces, and, of course, fantastic music performances. Velvet Goldmine is a must-see for fans of Bowie and movies about music.


Following IFC Films
Image Credit: IFC Films

Following is the small-budget, feature film debut from a little director named Christopher Nolan. Like many of Nolan’s films, Following is primarily a movie based on its high concept. Here that concept is a man who follows people to entertain himself and finds himself pulled into a criminal enterprise. It’s not a science fiction film, but Nolan’s fascination with time is already unmistakable as the non-linear narrative slowly comes together over the course of the film. It’s a great mystery and still one of the director’s best.


Pi Artisan
Image Credit: Artisan

Nolan wasn’t the only famous filmmaker who made his feature debut in 1998; Darren Aronofsky also appeared on the scene with Pi. Pi is a mind-bending thriller that follows a mathematician who encounters a number that seems to hold answers about the structure of the universe. As he attempts to make sense of this discovery through math and investigations into Kabbalah, more and more questions arise. Pi is a striking movie that will stick with you well after it ends.

Saving Private Ryan

saving private ryan
Image Credit: Dreamworks/Paramount Pictures.

While new directors were making their debuts, an established master delivered one of the best films of his career. Steven Spielberg’s Saving Private Ryan is one of the most beloved and powerful war movies ever made. The movie is largely remembered for its visceral depiction of the Normandy invasion, but the story about a small group of soldiers tasked with finding a young soldier and getting him home makes it a classic.

The Truman Show

The Truman Show
Image Credit: Paramount Pictures

The Truman Show tells the story of the titular Truman (Jim Carrey) as he discovers that his entire life is a fabrication made for a television show. It’s a movie that manages to be hilarious and poignant with its satire of the then-burgeoning reality TV genre in a way that has only become more relevant since it was made.


Image Credit:1998 New Line Cinema.

Black Panther gets a lot of well-deserved attention for bringing a black superhero to the MCU, but T’Challa wasn’t the first black superhero to grace the big screen. Before T’Challa, there were several others, but the best remains Wesley Snipes’ performance as the titular Blade in this movie adapted from the Marvel comics. The film sees Blade performing gravity-defying martial arts moves while decked out in black leather and dark sunglasses a year before the release of The Matrix.

SLC Punk!

SLC Punk Sony Pictures
Image Credit: Sony Pictures

SLC Punk centers on the life of Stevo (Matthew Lillard), the titular punk who lives in Salt Lake City. He goes to shows and parties with his friends, gets into relationships with girls, and ultimately begins to reassess his choices. It’s a coming-of-age movie that neither revels in nor disrespects the culture of its characters, highlighting the joys and dangers of punk life in the city during the mid-1980s in a way that feels authentic.

Out of Sight

Out of Sight Universal
Image Credit: Universal

Based on the novel of the same name by Elmore Leonard, Out of Sight remains one of Steven Soderbergh’s best crime films and by far his best romance. The story follows a prison escapee (George Clooney) and the U.S. Marshall (Jennifer Lopez) on his tail as they engage in a cat and mouse game that’s equal parts thriller, comedy, and romance. It’s a slick crime movie with an often suspenseful plot, but the real star is the chemistry between Clooney and Lopez.

The Faculty

The Faculty 1996
Image Credit: Miramax Films

Two years after writing the slasher parody classic Scream, Kevin Williamson wrote this almost equally parodic high school set take on Invasion of the Body Snatchers. The story follows a group of teens as they attempt to foil the attempts of the aliens that have begun taking over the bodies of, you guessed it, the faculty at their high school. The Faculty is also an early film from Robert Rodriguez, who is a master of the tongue-in-cheek tone displayed here. And to top it all off, it’s got a fantastic ensemble cast, including Salma Hayek, Elijah Wood, and Jon Stewart in one of his few acting roles.

Wild Things

Kevin Bacon Wild Things Columbia
Image Credit: Columbia Pictures

Perhaps best remembered for the scene of Denise Richards and Neve Campbell kissing in the pool, Wild Things has much more to offer than its most salacious moment. Wild Things is a densely layered neo-noir that takes viewers on a, well, wild ride of twists and turns that come so fast you don’t have a chance to catch your breath. Add to that the excellent cast, including Matt Dillon and Kevin Bacon, and you’ve got a sleazy fun mystery masterpiece on your hands.


Ringu Basara Pictures
Image Credit: Basara Pictures

While the 1980s may have a lock on the decade that introduced the most horror icons (including Freddy, Chucky, and Pinhead to name just a few), the 1990s introduced the world to a fair share of iconic horror movie monsters as well, and perhaps the greatest among them is Ringu’s Sadako. Based on the novel of the same name by Koji Suzuki, Ringu tells the story of a young woman who begins to investigate a mysterious videotape that leaves anyone who watches it dead within a week. She soon discovers that the tape is related to the violent death of a child seeking revenge, and an icon of horror is born. Ringu may not be as scary today as it was upon release, given that we no longer use VHS tapes, but the mystery at its center is still as enthralling as ever.


Mulan 2020 Walt Disney Pictures 2
Image Credit: Walt Disney Pictures

A high point of the Disney Renaissance, Mulan adapted the Chinese folk story for a modern children’s audience and gave us a classic. The story follows the titular Mulan (voiced by Ming-Na Wen) as she enlists, posing as a man in the Chinese army that’s attempting to save China from invasion. It’s surprising that a war movie about cross-dressing is as child friendly as it is, but Mulan remains one of the best Disney movies to this day.

Kuch Kuch Hota Hai

Kuch Kuch Hota Hai Dharma Productions
Image Credit: Dharma Productions

A Bollywood classic, Kuch Kuch Hota Hai tells the story of three friends who find themselves in a love triangle during college. The story plays out in two parts, one during their college years and another, years later, when two of the pair have had a child, but one of them has passed away. It’s a bittersweet but ultimately joyous movie about love, friendship, and grief. That tells its story as only the best of Bollywood can, with glorious use of color and at least three different songs that will be stuck in your head after viewing.


Ronin MGM
Image Credit: MGM

Ronin is a modern action classic for several reasons. The film offers an all-star cast, some of the most iconic car chases ever put to film, and a thrilling story that keeps you guessing until its final moments. It’s an action movie made with almost no digital effects, which means every action scene hits hard and leaves us in awe of the stunt performers’ talents.

The Parent Trap

parent trap dennis quaid natasha richardson 1
Image Credit Walt Disney Pictures

1998’s The Parent Trap is the rare example of a remake that’s better than the original. Based on the book Lottie and Lisa by Erich Kästner, the film tells the story of identical twins (Lindsay Lohan in an unforgettable dual role) separated at birth who scheme to get their parents back together. It’s a modern classic that made Lohan a star and is a high point in Nancy Meyers’ storied career.

Lock, Stock and Two Smoking Barrels

Lock Stock and Two Smoking Barrels Gramercy Pictures
Image Credit: Gramercy Pictures

Another debut from a director who would become a titan of the industry, Lock, Stock and Two Smoking Barrels marked the arrival of Guy Ritchie as England’s answer to Quentin Tarantino. The crime comedy follows a group of friends as they attempt to steal from a dangerous gang to pay back debts. Aside from being Ritchie’s debut, it also marks the first performances from ex-athletes Vinnie Jones and Jason Statham.

The Decline of Western Civilization Part III

The Decline of Western Civilization Part III Spheeris Films
Image Credit: Spheeris Films

The final film in director Penelope Spheeris’s The Decline of Western Civilization trilogy of music documentaries is just as fascinating as the two previous films and undoubtedly the most emotionally powerful. In Part III, Spheeris interviews young “gutter punks” who have decided to retreat entirely from polite society and live on their own, usually without a home. It’s a documentary that uses music as an entryway to exploring these young people’s lives more than a documentary about music.


Happiness Killer Films
Image Credit: Killer Films

Todd Solondz’s Happiness is a pitch-black comedy that plays almost like a parody of Paul Thomas Anderson’s Magnolia, even though it was released the year before. Happiness tells the story of several characters whose lives intersect. But nearly all the people in the movie are horrible. It’s a movie that pushes viewers to extreme discomfort and then challenges them to laugh. It’s not an easy film to watch, but for anyone who wants to go well beyond the cringe comedy of The Office, Happiness is a must-watch.

This article was produced and syndicated by Wealth of Geeks.

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