In the years since the 1990s, many of the movies that were released during this iconic decade for film have started to become dated and lose their edge. However, there is still an overwhelming number that have become iconic pieces of media from this decade, cementing their legacy as must-watch movies. There are certain films that are engaging and high-quality, but they’re only worth watching once. Fortunately, the ’90s are responsible for producing hilarious and heartfelt works that get better with every rewatch. The hit teen rom-com Clueless stands out thanks to its influence and legacy.
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Like Clueless, many of these movies from the 1990s are considered masterpieces, and this has been proven by the fact that they’ve aged so well, standing the test of time. Even elements that are noticeably dated are viewed as nostalgic rather than in poor taste. Though the styling and dialogue featured in these films are clearly a product of the ’90s, the themes and humor hold up well today, connecting with contemporary audiences. With well-known actors and filmmakers appearing across these projects, it’s easy to find something to love about each of them.
You are watching: Clueless & 9 Other Movies From The ‘90s That Get Better With Every Rewatch
10
Clueless (1995)
Directed by Amy Heckerling
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Clueless
PG-13
Comedy
Romance
9/10
10/10
Release Date
July 19, 1995
Runtime
97 minutes
Cast
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-
Alicia Silverstone
Cher
-
Stacey Dash
Dionne
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Alicia Silverstone stars as Cher Horowitz, the Beverly Hills princess who leads the cast of Clueless. Loosely adapted from the Jane Austen novel, Emma, Clueless pays tribute to the classic story beats Austen crafted but gives the narrative an updated twist. The rom-com genre has ebbed and flowed, but the 1990s saw the release of some of the most enduring, as the late ’80s through the ’90s are often described as the golden age of the rom-com.
Clueless is a prime example of why this period is so acclaimed for its contributions to romantic comedies.
Clueless is a prime example of why this period is so acclaimed for its contributions to romantic comedies. While the original story from Austen has helped the movie retain its relevance and reliability, there’s also a great balance of self-awareness and sincerity that few movies achieve today. Though Clueless got a spinoff TV series, this show could never capture the magic of the original story, which can be felt all these years later.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Clueless (1995) |
81% |
76% |
9
Boyz N The Hood (1991)
Directed by John Singleton
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Boyz n the Hood
R
Crime
Documentary
Drama
9/10
Release Date
July 12, 1991
Runtime
102 minutes
Cast
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-
Hudhail Al-Amir
-
Lloyd Avery II
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One of the quintessential ’90s LA movies, Boyz n the Hood, was the feature debut of director John Singleton and successfully catapulted its many stars to fame. A young Cuba Gooding Jr. leads the cast as Tre, the young man growing up in the predominantly Black Crenshaw neighborhood of LA. Tre is the audience’s window into the world of the film, and Boyz n the Hood does an excellent job of taking every moment of Tre’s life seriously, from smaller romantic dramas to devastating loss.
While every performance remains as potent as it was in 1991, Laurence Fishburne’s performance as Furious is a major highlight of his career, and he’s a critical piece of the story. Furious is the character who frequently lays out the realities of life as a Black man in Los Angeles. Though Boyz n the Hood tackled the contemporaneous racial and social issues of LA in the ’90s, many of these conversations are just as relevant, if not more so, today.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Boyz n the Hood (1991) |
96% |
93% |
8
The Truman Show (1998)
Directed by Peter Weir
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The Truman Show
PG
Drama
Sci-Fi
Comedy
10/10
9/10
Release Date
June 5, 1998
Runtime
103 minutes
Cast
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Ed Harris
-
Natascha McElhone
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The Truman Show is credited with helping audiences and critics recognize Jim Carrey as a dramatic performer after years of being known exclusively for comedic work. While there are plenty of hilarious moments in The Truman Show, the heart of the film is desperately sad and critical of the rising problems of surveillance and performative living in society. It’s almost shocking how The Truman Show predicted how much of life would come to look like the dystopian version of reality it represents.
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This relevance and understanding of the trajectory of technology and media are what have kept The Truman Show at the forefront of cultural conversations. While there’s something eerie about the similarities between The Truman Show and our real lives, the film still ends on an unabashedly hopeful note. Truman ultimately exercises his free will and refuses to capitulate to his audience, choosing the uncertainty of real life instead. Carrey’s performance gives us a sensitive and vulnerable insight into this character.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
The Truman Show (1998) |
94% |
89% |
7
Fargo (1996)
Directed by Joel & Ethan Coen
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Fargo
R
Crime
Thriller
10/10
Release Date
April 5, 1996
Runtime
98 Minutes
Cast
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-
William H. Macy
-
Frances McDormand
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The Coen Brothers’ frequent collaborator Frances McDormand is hilarious in this darkly comic addition to the filmmakers’ oeuvre. She’s one of many performers featured in the film who have gone on to have illustrious filmographies. The work of the actors in Fargo is a significant factor in the film’s longevity, as they all understand the unique tone and idiosyncratic formula of a Coen Brothers movie. This style is what sets Fargo apart, making it instantly recognizable as a project from the filmmakers.
The fact that Fargo went on to inspire the highly successful anthology TV series of the same name speaks to its ability to capture our attention years later. Crime dramas are inherently popular, but most of us expect movies within the genre to follow a specific set of steps and tropes. Fargo subverts our expectations at every turn, remaining fresh and offering something new to uncover with every successive viewing.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Fargo (1996) |
95% |
92% |
6
Malcolm X (1992)
Directed by Spike Lee
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Malcolm X
PG-13
Biography
Drama
History
12
9.2/10
Release Date
November 18, 1992
Runtime
202 minutes
Cast
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-
Denzel Washington
-
Angela Bassett
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One of Denzel Washington’s most rewatchable movies, Malcolm X, demonstrates an unforgettable side of Washington, cementing him as one of the greatest actors of his generation. The genre-bending biopic, directed by the visionary Spike Lee, focuses on the different points of Malcolm X’s life, playing with the timeline and perspectives to paint an emotionally resonant picture of both a well-known social and political figure and a man. It can be difficult for a biopic to balance the truth of a person’s life with a compelling cinematic narrative, but Malcolm X achieves both.
Without Washington’s work, the film would still be a vital piece of cinematic history, but he elevates the film, taking it to another level.
Without Washington’s work, the film would still be a vital piece of cinematic history, but he elevates the film, taking it to another level. In the years since it was released, Malcolm X has only grown in importance. X’s life and contributions to the fight for civil liberties are part of U.S. history and shouldn’t be forgotten. However, outside of its social and political impact, Malcolm X is simply a compelling and moving movie to be enjoyed.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Malcolm X (1992) |
89% |
91% |
5
Velvet Goldmine (1998)
Directed by Todd Haynes
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Velvet Goldmine
R
Drama
Music
Release Date
August 28, 1998
Runtime
123 minutes
Cast
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-
Ewan McGregor
Curt Wild
-
Jonathan Rhys Meyers
Brian Slade
-
Toni Collette
Mandy Slade
-
Christian Bale
Arthur Stuart
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The non-linear storytelling style of Velvet Goldmine has allowed the film to age well, as modern audiences are more ready than ever to engage with non-traditional narrative structures. Loosely based on the bisexual and gay glam rock stars of the 1970s, Velvet Goldmine is entranced by the legacy of its fictional David Bowie-esque rock star, Brian Slade (Jonathan Rhys Meyers). Rhys Meyers is far from the only big name in the cast, as he’s joined by Christian Bale and Ewan McGregor.
Though Velvet Goldmine drew some criticism for its surrealist elements and allusions to the real glam rock figures of its time, these are the parts of the film that have allowed it to endure. The director, Todd Haynes, would take a similar approach to the life of Bob Dylan with his 2007 film I’m Not There, using style and theme to communicate the facts of its subjects’ lives rather than fact. In some ways, this offers more truth and emotional realism than many contemporary music biopics.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Velvet Goldmine (1998) |
63% |
80% |
4
Election (1999)
Directed by Alexander Payne
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Election
tv-ma
Comedy
Release Date
April 23, 1999
Runtime
103minutes
Cast
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-
Reese Witherspoon
-
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Matthew Broderick
-
Chris Klein
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Reese Witherspoon and Matthew Broderick are at their best as the precocious high schooler Tracy Flick and the teacher with a vendetta against her, Jim McAllister. Though the movie deals with the pangs of adolescence and the challenges of trying to fit in during high school, it’s clear from the first moments of the story that it’s much more than that. The conflict between Tracy and McAllister might play out through small, petty dramas, but it represents the intensity of power dynamics between teachers and students, even at this micro level.
The film is critical of everyone in it, not just Tracy and McAllister, who quickly prove themselves to be equally unscrupulous in carving out a place for their ambition and desire for power.
Hilarious and compulsively watchable from beginning to end, Election quickly became a cult classic and has aged better than many high school movies of the ’90s. The film is critical of everyone in it, not just Tracy and McAllister, who quickly prove themselves to be equally unscrupulous in carving out a place for their ambition and desire for power. It’s easy to take the takes of this high school class election seriously even as we laugh at the archetypal characters who populate the world.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Election (1999) |
92% |
79% |
3
Unforgiven (1992)
Directed by Clint Eastwood
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Unforgiven
R
Western
Drama
16
9.4/10
Release Date
August 7, 1992
Runtime
130 Mins
Cast
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-
Clint Eastwood
Bill Munny
-
Gene Hackman
Little Bill Daggett
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Clint Eastwood has directed and starred in plenty of iconic movies throughout his long career, but Unforgiven might be his best. Unforgiven is both a love letter to the Western genre and a critical evaluation of what we’ve come to believe about the genre. After playing the archetype of the rugged lone gunslinger for most of his early career, Eastwood grappled with what it meant for him to be aging out of this role and how this is a metaphor for the genre as a whole.
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1
Unforgiven reflects on how the Western has changed and if there’s a place for it in Hollywood anymore. It’s the culmination of years of work on these stories and could only be brought to life by a veteran of the industry like Eastwood. Unforgiven is a Western that would win the Oscar for Best Picture today, which is a good indication of how well it’s aged. Even though Eastwood has branched off from the Western since then, Unforgiven will likely remain his magnum opus.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Unforgiven (1992) |
96% |
93% |
2
Princess Mononoke (1997)
Directed by Hayao Miyazaki
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Princess Mononoke
PG-13
Animated
Epic
Historical
Fantasy
9.3/10
Release Date
July 12, 1997
Runtime
133 Minutes
Cast
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-
Yôji Matsuda
-
Yuriko Ishida
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One of the most visually stunning movies of the 1990s, Princess Mononoke, exemplifies how and why Studio Ghibli and its visionary director, Hayao Miyazaki, have remained so popular. Like many of Miyazaki’s most iconic films, Princess Mononoke is a story outside of time that transports us to a new, vividly imagined world. However, within this narrative, there’s no shortage of thematic messaging communicating what we should be taking away from this work.
Time has been kind to Princess Mononoke, demonstrating how enduring its themes are and hitting all of its beats just as successfully today as in 1997.
Princess Mononoke encourages us to remember our deep connection to the Earth and the balance of its ecosystems, demonstrating the disaster that strikes if this harmony isn’t respected. Time has been kind to Princess Mononoke, demonstrating how enduring its themes are and hitting all of its beats just as successfully today as in 1997. It’s difficult to find any faults within Princess Mononoke, from its perfectly crafted setting to the universal emotional journey.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Princess Mononoke (1997) |
93% |
94% |
1
The Player (1992)
Directed by Robert Altman
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The Player
R
Mystery
Drama
Comedy
Crime
Release Date
April 3, 1992
Runtime
124 minutes
Cast
See All
-
Tim Robbins
-
Greta Scacchi
-
Whoopi Goldberg
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Though The Player is made for audiences interested in the film industry and the changeable nature of Hollywood, there’s something in this dark satire for everyone. Starring Tim Robbins as Griffin Mill, a Hollywood executive who commits murder, The Player quickly spins out of control as Griffin attempts to cover up his crime, maintain control of his career, and develop a relationship with the girlfriend of his victim. It’s a twisting and dark story, anchored by Robbins’ fantastic performance.
In the years since The Player was released, Hollywood might have changed, but much of the ambition, cut-throat behavior, and privileged exceptionalism the characters experience still rings true. The director, Robert Altman, helmed many great films set in Los Angeles that challenge genre conventions, like The Long Goodbye. The Player also demonstrates the disillusionment with the establishment felt in the 1990s, coupled with the comfortable corporate atmosphere so prevalent at the time.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
The Player (1992) |
97% |
84% |
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Category: Entertainment