10 Great Films That Flopped in the Last 20 Years

Let’s look back at 10 of the best money-losing movies over the last couple of decades.

1. The Hudsucker Proxy (1994)

Joel and Ethan Coen’s fond sendup of 1930s screwball comedies was an ingeniously plotted story of a neophyte businessman (Tim Robbins) charged with becoming the puppet leader of a corporation that wants to depress the stock price. Instead, he turns out to be an entrepreneurial visionary who invents the hula hoop. An irascible Paul Newman is hilarious as the scheming board member frustrated by the simple honesty of the Robbins character. The movie deserves the cult success that later attached to The Big Lebowski.


2. The Shawshank Redemption (1994)

Though it received 7 Oscar nominations including Best Picture, and is the no. 1 film of all time based on imdb.com’s reader poll, this 1940s drama proved difficult to market: It was a thoughtful, action-free period piece about the rebuilding of a man’s soul, it was uncharacteristic of Stephen King (who wrote the story upon which it was based) and neither Tim Robbins nor Morgan Freeman was a big name at the time. Nevertheless, the film’s combination of plot surprises and soul cleansing made it both a huge entertainment and a profoundly affecting experience.

3. Strange Days (1995)

Back in the virtual-reality craze of the 1990s, director Kathryn Bigelow found a fresh and interesting way to approach the subject, as thrill-seekers buy bootlegs that allow them to jack into others’ experiences. Naturally, the equivalent of a snuff tape becomes one such bootleg. Bigelow’s vision of a none-too-distant-future set at the turn-of-the-century was a potent, unsettling consideration of how ethnic tensions, police abuses and technology can inflame one another.

4. Casino (1995)

It’s just a notch below Goodfellas in quality, and yet Casino, which was glitzier and no doubt more expensive to film, grossed only $42 million. Few films delved into their subjects with more gusto, and it’s impossible to see Las Vegas the same way after this fact-based film laid bare the dirty dealings behind the scenes. Smart, tough, and cynical, this mob movie is not only fascinating in its level of detail but also has, for a Scorsese movie, a surprisingly convincing love story between the betting maestro played by Robert De Niro and the mindless floozy (Sharon Stone) he can’t help marrying. 


5. Office Space (1999)

Hard to believe such a smart, knowing comedy could only gross $11 million, but character-based comedy doesn’t come through in a trailer. Maybe there should have been more vomit jokes? Anyway, analysis of TPS reports confirms that writer-director Mike Judge nailed the Dilbert life of being a cubicle drone in this breezy, smart, brilliantly observed hunk of gray climate-controlled existence.

6. Fight Club (1999)

A highly touted film that delivered only $37 million in U.S. grosses, this dark comic satire cost Fox Studios chief Bill Mechanic his job. Like most of the films on this list, the Brad Pitt-Edward Norton film was impossible to summarize in a 30-second TV commercial. It remains director David Fincher’s most dizzying, imaginative and incendiary film, though its chaotic last act doesn’t live up to the setup or the brilliant twist.

7. A.I. Artificial Intelligence (2001)

Cool and cerebral for a sci-fi movie, this expensive amalgam of the visions of Stanley Kubrick (who spent years developing it before his death) and Steven Spielberg (who took over after that) wasn’t aimed at people looking for a fun summer blockbuster. But the enduring Pinocchio-like story of a robot boy (Haley Joel Osment) who yearns to reconnect with the human mother who treated him as her own son was rendered with heartbreaking sensitivity by Spielberg, who suffused the film with a sublime fairy-tale imagination yet kept his eye on the universality of the need to be loved.


8. Team America: World Police (2004)

Trey Parker and Matt Stone came up with some of the most outlandish, contrarian and hilarious sequences ever put on film in this spoof of action movies whose marionette characters mocked such evildoers as Kim Jong Il, Matt Damon and Sean Penn. Daring to call out liberal Hollywood on its hypocrisies and knee-jerk anti-Americanism, the film was one of the very few comedies that merit the adjective “daring.”

9. Idiocracy (2006)

Fox buried this film before it was even released, hiding it from critics and hardly spending anything on publicity. It grossed less than half a million dollars, but its vision of a commercial-saturated future run by increasingly huge corporations backed by a gleefully brain-dead populace was far more dead-on than the meandering, warmed-over George Orwell of the much more acclaimed Brazil.

10. The Assassination of Jesse James by the Coward Robert Ford (2007)

Long, strange and mesmerizing, this elegy for the Western outlaw reimagined the train robber James as an aging celebrity and his gang member Ford as a jealous nobody who craved the spotlight that only betrayal and murder could bring him. Pitt is reserved and haggard as James, but the true stars of the film are a sniveling, poisonous Casey Affleck as his Judas and cinematographer Roger Deakins, who gives the film a shivery, yellowing tone that conjured up a sense of fading wisps of legend. Here’s hoping director Andrew Dominik (who went on to make the disappointing Killing Them Softly) returns to form soon.



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