10 25-Year-Old Movies That Are Perfect From Start to Finish (2025)

10 25-Year-Old Movies That Are Perfect From Start to Finish (1)

By Bankole Imoukhuede

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10 25-Year-Old Movies That Are Perfect From Start to Finish (2)

The factors that need to fall into place to create an excellent film year can never be predicted. Sometimes, even after the fact, it might be impossible to individually pinpoint what leads to a standout year at the cinemas. However, what is beyond reproach is the body of work that ineffable alchemy creates. 1999 is one such year when everything seemed to fall into place exactly right.

Placed in isolation, 1999 is an interesting film year. It sits at the end of a great decade of independent, mid-sized and blockbuster filmmaking and comes right before Hollywood will forever be changed with the start of the Spider-Man, Harry Potter, X-Men and The Lord of the Rings franchises. The year featured many films that would redefine the industry. It saw the posthumous release of Stanley Kubrick's final film, introduced the world to British trio Guy Ritchie, Jason Statham and Vinnie Jones via Lock, Stock and Two Smoking Barrels, ushered in Sofia Coppola's directorial debut and saw the return of Star Wars to the big screen. While commiserations are owed to David Fincher's Fight Club, Alexander Payne's Election and many more great films, these are the films from an electric 12 months that remain perfect 25 years later.

10 'Being John Malkovich'

Directed by Spike Jonze

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Perhaps the most out-there film of 1999, Being John Malkovich introduced audiences to the surreal minds of Spike Jonze and Charlie Kaufman. In the film, John Cusack plays puppeteer Craig Schwartz, who, while working as a clerk, finds a portal that leads him into the mind of Academy Award nominee John Malkovich. When inside, Schwartz can control Makovich's mind and body. Besides Cusack and Malkovich, the film also features Cameron Diaz and Catherine Keener.

An absurdly surreal and hilarious film, Being John Malkovich received near-unanimous critical praise. The inventiveness of the premise and execution was consistently highlighted, as was Charlie Kaufman's script and his ability to perfectly balance many weighty ideas. Catherine Keener received an Academy Award nomination for her performance and Spike Jonze and Charlie Kaufman were nominated for the film's directing and screenplay, respectively.

10 25-Year-Old Movies That Are Perfect From Start to Finish (4)

Being John Malkovich

R

Comedy

Drama

Fantasy

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Release Date
October 29, 1999
Cast
John Cusack, John Malkovich, Cameron Diaz, Catherine Keener, Mary Kay Place, Orson Bean, Charlie Sheen, Reggie Hayes, W. Earl Brown, Carlos Jacott, Willie Garson, K.K. Dodds, Byrne Piven, Judith Wetzell, Gregory Sporleder, Octavia Spencer, Ned Bellamy, Eric Weinstein, Madison Lanc, Kevin Carroll, Gerald Emerick, Richard Fancy, Patti Tippo, Daniel Hansen, Mariah O'Brien

Runtime
113 minutes

9 'Eyes Wide Shut'

Directed by Stanley Kubrick

10 25-Year-Old Movies That Are Perfect From Start to Finish (6)

Stanley Kubrick's final film, Eyes Wide Shut, was one of two Tom Cruise dramatic roles this year. The film starred the at-the-time real-life couple Tom Cruise and Nicole Kidman, alongside Sydney Pollack, Todd Field and Marie Richardson. In the erotic thriller, Tom Cruise plays a successful doctor whose beliefs are shaken when his wife (Kidman) reveals that she considered having an affair and leaving him and their daughter a year earlier. Cruise's Bill Harford then spends a night exploring a masked orgy at an unnamed secret society.

Eyes Wide Shut tackles several transgressive topics head-on, most especially those related to sex. The film analyzes the primal desires of both genders and earnestly examines sexual depravity and amorality. Despite being something of a box office success, Eyes Wide Shut developed a reputation for being confrontational and even inaccessible, making it fodder for a very particular type of viewer.

10 25-Year-Old Movies That Are Perfect From Start to Finish (7)
Eyes Wide Shut

R

Mystery

Thriller

Drama

Where to Watch

*Availability in US

Release Date
July 16, 1999
Cast
Marie Richardson, Todd Field, Sydney Pollack, Nicole Kidman, Tom Cruise

Runtime
159 minutes

Writers
Stanley Kubrick, Frederic Raphael

8 'Magnolia'

Directed by Paul Thomas Anderson

Paul Thomas Anderson's third film, Magnolia, is an epic ensemble film about the lives of several San Fernando Valley inhabitants. The large ensemble cast includes Tom Cruise, Philip Seymour Hoffman, John C. Reilly, Julianne Moore, Philip Baker Hall, William H. Macy, and more. Anderson began writing the script to give a more grand treatment to ideas and characters that are not usually afforded that luxury. The writing process then evolved into him writing certain characters and scenes for specific actors.

The film received widespread praise, mostly for Anderson's script and the strength of its characters. Out of the excellent ensemble, Tom Cruise was singled out for the most praise, and he received his third and, so far, last Academy Award nomination. Meanwhile, Paul Thomas Anderson's script for the film was also Academy Award-nominated. Almost three decades later, the praise still rings true, and Magnolia is as essential as when it debuted.

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7 'Notting Hill'

Directed by Roger Michell

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With the release of Pretty Woman at the start of the decade, Julia Roberts staked her claim as the next great rom-com movie star. To cap off a decade that produced many more excellent romantic comedies, she combined her unending charm with that of Hugh Grant — who had recently announced his arrival with Four Weddings and a Funeral — to produce the box office hit Notting Hill.

The film portrays the unlikely romance between an American movie star (Roberts) and a British bookseller (Grant). Notting Hill was an immediate critical success upon arrival and remains a crucial Gen X rom-com. However, in the years since, its reputation has continued to grow, and it is now regarded as one of the best in the genre. A charming and endearing film, Roberts and Grant's performances rubber-stamped their already confirmed rom-com reputations.

10 25-Year-Old Movies That Are Perfect From Start to Finish (20)

Notting Hill

pg-13

Romance

Comedy

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Release Date
May 13, 1999
Cast
Julia Roberts, Hugh Grant

Runtime
124minutes

Writers
Roger Michell

6 'The Blair Witch Project'

Directed by Daniel Myrick and Eduardo Sánchez

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Made on an initial budget of $60,000, The Blair Witch Project was a critical hit and became one of the most successful films ever made with its nearly $250 million box office return. The film uses found footage to tell the story of three film students on a hike to shoot a documentary about the Blair Witch, a local myth. The Blair Witch Project became a standout horror film of the decade and has influenced many films in the genre.

Largely improvised, it blurred the lines between real and fake for most audiences. To aid the film's found footage technique, the marketing leaned into the plot's sense of authenticity by creating newspaper articles and news segments about the "missing" students. Thanks to its excellent marketing and positive word-of-mouth, The Blair Witch Project became a sleeper hit and a seminal entry in modern horror. It introduced the found-footage subgenre and revolutionized movie marketing, becoming a true before-and-after in modern entertainment.

10 25-Year-Old Movies That Are Perfect From Start to Finish (24)
The Blair Witch Project

R

Horror

Mystery

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Release Date
July 30, 1999

Cast
Joshua Leonard, Michael C. Williams, Heather Donahue

Runtime
81 minutes

Writers
Daniel Myrick, Eduardo Sánchez

5 'The Insider'

Directed by Michael Mann

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Following their collaboration on 1995’s Heat, which was inspired by real-life events, Michael Mann and Al Pacino reunited for a more factual drama in 1999’s The Insider. The film was based on a 1996 Vanity Fair article and adapted by Mann and Eric Roth. Russell Crowe and Christopher Plummer joined Al Pacino for the film.

The Insider centers on a 60 Minutes segment about tobacco whistleblower Jeffrey Wigand. The film depicts the struggles he and Lowell Bergman, a CBS producer, encountered as they defended his testimony against allegations from both Wigand’s former employer and CBS. A lot of praise was afforded to Mann for his entertaining direction of the material. The script was further praised for its ability to entertain and provoke anger. The Insider received seven Academy Award nominations, including Best Picture, Best Director, Best Actor and Best Adapted Screenplay.

10 25-Year-Old Movies That Are Perfect From Start to Finish (29)
The Insider

R

Drama

Biography

Thriller

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Release Date
November 5, 1999
Cast
Russell Crowe, Al Pacino, Christopher Plummer, Diane Venora, Philip Baker Hall, Lindsay Crouse, Debi Mazar, Stephen Tobolowsky

Runtime
157 Minutes

Writers
Marie Brenner, Eric Roth, Michael Mann

4 'The Matrix'

Directed by The Wachowskis

10 25-Year-Old Movies That Are Perfect From Start to Finish (30)

Every so often, there comes a film that completely redefines the capabilities and limits of its genre. In 1999, The WachowskisThe Matrix was just that. The film is a science-fiction, martial arts action tale that depicts a dystopian future where humanity is trapped in a simulated reality called The Matrix. Already an action star on the rise thanks to roles in Point Break and Speed, The Matrix certified Keanu Reeves as an action movie star and box office draw. Joining him in the film’s cast were Laurence Fishburne, Carrie-Anne Moss, Hugo Weaving and Joe Pantoliano.

The Matrix spawned a multimedia franchise of sequels, comic books, animated entries and video games. It examines the subjugation of humans by the machines controlling the simulation and the resistance fighting against the machines. The Matrix's stunt work, aesthetic and special effects have been repeatedly praised and have influenced a generation of films since its release.

10 25-Year-Old Movies That Are Perfect From Start to Finish (31)

The Matrix

R

Action

Adventure

Sci-Fi

Where to Watch

*Availability in US

Release Date
March 31, 1999
Cast
Keanu Reeves, Laurence Fishburne, Carrie-Anne Moss, Hugo Weaving, Gloria Foster, Joe Pantoliano

Runtime
136 minutes
Writers
Lilly Wachowski, Lana Wachowski

3 'The Sixth Sense'

Directed by M. Night Shyamalan

10 25-Year-Old Movies That Are Perfect From Start to Finish (46)

"I see dead people." M. Night Shyamalan’s third feature film is also his most often quoted. Starring Bruce Willis, Haley Joel Osment. and Toni Collette, The Sixth Sense follows a child psychologist played by Bruce Willis, whose patient (Haley Joel Osment) claims to be able to see and communicate with dead people. The psychological thriller was widely praised for its performances and Shyamalan’s screenplay and direction.

In addition to a Best Picture nomination, The Sixth Sense received individual Academy Award nominations for Collette and Osment. The film, which was made for $40 million, was a box office hit, making over $672 million on the way to being the second-highest-grossing film of the year. Twenty-five years later, The Sixth Sense still reigns as one of the horror genre's most exciting entries.

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The Sixth Sense

PG-13

Thriller

Drama

Horror

Mystery

Where to Watch

*Availability in US

Release Date
August 6, 1999
Cast
Bruce Willis, Toni Collette, Haley Joel Osment, Olivia Williams, Donnie Wahlberg

Runtime
107 minutes
Writers
M. Night Shyamalan

2 'The Talented Mr. Ripley'

Directed by Anthony Minghella

10 25-Year-Old Movies That Are Perfect From Start to Finish (61)

1999’s The Talented Mr Ripley is the second adaptation of Patricia Highsmith’s first novel in her Ripley series. The film stars Matt Damon as Tom Ripley, a low-level con artist sent to Italy by a rich shipbuilding magnate (James Rebhorn) to convince his son, Dickie Greenleaf (Jude Law), to return to America. When in Italy, Ripley quickly becomes seduced by the lifestyle Dickie and his girlfriend, Marge (Gwyneth Paltrow), have grown accustomed to, leading him down dark paths. Cate Blanchett and Philip Seymour Hoffman round out the film’s main cast.

Despite multiple adaptations of both The Talented Mr Ripley and the other novels in Highsmith’s series, Anthony Minghella’s film remains the most famous Ripley adaptation. The film was nominated for five Academy Awards, including for Minghella’s script and Jude Law’s supporting performance. Sun-kissed, seductive, and genuinely tense, The Talented Mr. Ripley is among the best thrillers of the '90s.

10 25-Year-Old Movies That Are Perfect From Start to Finish (62)

The Talented Mr. Ripley

r

Thriller

Drama

Crime

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Release Date
December 25, 1999
Cast
Matt Damon, Gwyneth Paltrow, Jude Law, Cate Blanchett, Philip Seymour Hoffman, Jack Davenport, James Rebhorn, Philip Baker Hall

Runtime
139 minutes

Writers
Anthony Minghella

1 'Toy Story 2'

Directed by John Lasseter, Ash Brannon and Lee Unkrich

10 25-Year-Old Movies That Are Perfect From Start to Finish (67)

It is very rare for a sequel to be considered perfect, especially a sequel to a film as beloved as 1995’s Toy Story. Again featuring the voice talents of Tom Hanks, Tim Allen, Don Rickles and many more, Pixar’s Toy Story 2 sees the toys on a journey to save Woody from a toy collector who steals him.

Instantly acclaimed and revered as a modern animation classic, Toy Story 2 grossed almost $500 million at the box office, out-grossing its predecessor and becoming the third-highest-grossing film of the year. The film was widely praised for its ability to maintain the spirit of the original without re-treading the story. It was immediately popular, and over the years, many fans and critics have argued that Toy Story 2 is equal or superior to the franchise's first film.

10 25-Year-Old Movies That Are Perfect From Start to Finish (68)

Toy Story 2

G

Animation

Adventure

Comedy

Family

Fantasy

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Release Date
November 24, 1999
Cast
Tim Allen, Tom Hanks, Joan Cusack, Annie Potts, Kelsey Grammer

Runtime
92 minutes

Writers
Rita Hsiao, Andrew Stanton, Chris Webb, Doug Chamberlin

NEXT: The 10 Best Independent Movies of 1999, Ranked

  • The Sixth Sense

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