The Biggest Box Office Bomb: Cut Throat Island

The largest net loss ever recorded in film goes to the feminist pirate epic Cutthroat Island starring Geena Davis. The film cost a staggering $115 million to produce but made a paltry $10 million at the box office. The losses reported from this film forced one-time production giant Carolco Pictures (The Rambo Series, Total Recall) into bankruptcy after yet another disaster Showgirls. The film was lambasted by critics as “strangely devoid of any genuine fun or excitement,” and effectively killed Geena Davis’ chances of ever becoming a bankable star, relegating the actress to a failed sitcom and a brief run as the first female president in Commander in Chief. Perhaps the film suffered because Davis’ then husband Renny Harlin directed the feature and cast his wife in the main role, usually not the best idea (see Swept Away). The worst part about this film is that even now it is completely unwatchable. Unlike other box office disasters like Battlefield Earth or The Adventures of Pluto Nash, which enjoy a cult following for how awful they are, Cutthroat Island is worse than awful… it’s boring.

The Worst Reviewed Film of All Time: Bucky Larson-Born to Be a Star

Bucky Larson marks the magnum opus of Adam Sandler’s Happy Madison Production’s string of terrible movies including Jack and Jill, You Don’t Mess with the Zohan, and Benchwarmers. The story follows Bucky Larson, played by Nick Swardson, a small town grocery store clerk who discovers that his conservative parents were once adult film stars. Upon gaining this information Bucky flies out the Los Angeles to follow in their footsteps only to be informed that he has a micropenis. That’s the plot. The film aspires to be the anti-Boogie Nights but suffers from extremely underdeveloped writing and repetition of the same joke for an hour and a half. One reviewer put it perfectly, “A comic monstrosity…plays like an unfunny idea for a raunchy five-minute sketch that’s been cruelly extended to an insufferable ninety-six minutes.” Co-starring bad movie magnet Steven Dorff, Bucky Larson is the perfect example of how Adam Sandler has definitely lost “the funny” and makes you wonder if he ever had it in the first place.

Biggest On Set Disaster: The Conqueror

There have been many well known on-set accidents, like the death of Brandon Lee while filming The Crow, but few people know the production of Howard Hughes’ epic The Conqueror led to 91 members of the cast and crew contracting cancer including stars John Wayne, Susan Hayward, Agnes Moorehead and director Dick Powell. Experts attribute the large number of cancer diagnoses to the nuclear fallout from atomic bomb testing in nearby Nevada. The worst part about this tragedy? Nobody was allowed to see the movie for almost twenty years after production halted. Why? Hughes apparently despised the film so much that he purchased every copy of the reel so that it would never be seen by the general public. In his later, more paranoid, years Hughes would allegedly screen the film every night to remind himself of what a massive failure it was. It wasn’t until 1974 that Paramount would reach a deal with Hughes to allow it’s distribution.

The Most Unfortunate Film Shoot: The Man Who Killed Don Quixote

Terry Gilliam wins the prize for most unforeseen complications during a film shoot for his 2000 film The Man Who Killed Don Quixote which was so mired with bad luck that it never even finished production. The Brazil director’s many misfortunes include an $8 million cut to his budget, military jets constantly flying over a main shooting location, a flash flood washing away equipment, and the lead actor suffering from a double herniated disc forcing the production to halt indefinitely. The entire disaster was chronicled in the documentary Lost in La Mancha which features a very pissed off Terry Gilliam scrambling to deal with the mounting number of issues plaguing the film. Gilliam has since tried to get the project back on its feet with a new script and cast but no news of the film has been released since 2010.

Worst Film Adaptation/Sequel: Catwoman

Halle Berry’s turn as the Batman antagonist Catwoman is widely regarded by the comic book community as the worst superhero movie ever made. All but destroying the source material, Catwoman ignores the origin story set up in the DC comics mythology giving Catwoman superpowers and the ability to jump from rooftop to rooftop in stiletto heels. How does Halle get these powers? She drowns in a pipe and a magical cat brings her back to life… Additionally, producers of the film decided to ditch the iconic Lycra body suit characteristic of Catwoman in favor of skin tight leather jeans and a bra. The film was so bad that one critic suggested that Berry give back her 2001 Academy Award. The production company also lost boatloads of money trying to merchandise the film with action figures and the ill-conceived concept of selling diamond Catwoman claws.