7 '90s Movies That Nearly Reached Masterpiece Status

From 'The Crying Game' to 'Shakespeare in Love', these films came close but fell just short of perfection.

Feb. 22, 2026 at 5:55pm

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The 1990s were a landmark decade for cinema, producing many outright masterpieces. However, the decade also gave us a number of films that came extremely close to perfection but fell just short. Movies like 'The Crying Game', 'Quiz Show', 'Casino', and 'Jackie Brown' are considered near-masterpieces, showcasing incredible performances, writing, and filmmaking, even if they don't quite reach the heights of the era's true classics.

Why it matters

The '90s were a transformative time for film, with a wave of auteurs and independent voices emerging to challenge the studio-driven atmosphere of the previous decade. While not every movie from this period achieved perfection, these near-masterpieces highlight the creativity, risk-taking, and high standards that defined '90s cinema, cementing the decade's legacy as one of the greatest in movie history.

The details

The article examines seven '90s films that came tantalizingly close to masterpiece status but fell just short for various reasons. These include the genre-blending thriller 'The Crying Game', the historical drama 'Quiz Show', Martin Scorsese's sprawling crime epic 'Casino', the beloved teen comedy 'Clueless', the sports romance 'Jerry Maguire', Quentin Tarantino's underappreciated 'Jackie Brown', and the period piece 'Shakespeare in Love'. Each film is praised for its strong performances, distinctive style, and thematic ambition, even as the author acknowledges their minor flaws or shortcomings that prevent them from reaching the highest echelon of '90s cinema.

  • The Crying Game was released in 1992.
  • Quiz Show was released in 1994.
  • Casino was released in 1995.
  • Clueless was released in 1995.
  • Jerry Maguire was released in 1996.
  • Jackie Brown was released in 1997.
  • Shakespeare in Love was released in 1998.

The players

Neil Jordan

The director of The Crying Game.

Robert Redford

The director of Quiz Show.

Martin Scorsese

The director of Casino.

Amy Heckerling

The director of Clueless.

Cameron Crowe

The writer and director of Jerry Maguire.

Quentin Tarantino

The writer and director of Jackie Brown.

John Madden

The director of Shakespeare in Love.

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What they’re saying

“The '90s gave us many masterpieces — too many, in fact. Yet, it also gave us a slew of movies that came extremely close to perfection but didn't quite reach it.”

— David Caballero, Author

“Sure, its treatment of gender themes leaves a lot to be desired when judged with a 2026 eye, but in 1992, The Crying Game was a bold step for LGBTQ+ cinema, especially considering its ending.”

— David Caballero, Author

“In a year of cinematic titans, Quiz Show often gets overlooked — indeed, it's the forgotten one when discussing the 1995 Best Picture nominees. However, it deserves far more attention as a near-masterpiece of the '90s.”

— David Caballero, Author

“Scorsese treads familiar ground with a much more brutal approach, and the result is a movie that, while not among his masterpieces, is still an exhilarating and insightful look into the criminal underworld.”

— David Caballero, Author

“The controversy behind it might be strong enough to cloud its many achievements, but the film itself is a triumph of historical fiction that deserves its place as one of the movies of the '90s.”

— David Caballero, Author

The takeaway

While not achieving the status of true masterpieces, these '90s films showcase the creativity, ambition, and high standards that defined the decade's cinematic landscape. Though they may have minor flaws, they remain beloved by audiences and critics alike, cementing the '90s as one of the greatest eras in modern film history.