For James Brooks, the director of the romantic comedy-drama film, “How Do You Know,” it’s not just a flop, it is a career-ender. Responsible for such memorable and funny hits (“Terms of Endearment,” “As Good As It Gets,” and “The Mary Tyler Moore Show,” and wielding a powerhouse (and very expensive) cast including Reese Witherspoon, Jack Nicholson, Paul Rudd, and Owen Wilson — Brooks just didn’t pull it off. It cost the production team $10 million for his time as director of the 2010 release.
Great director, a stellar cast, and one of the most expensive losses ever. The budget for the Sony Pictures flop was $100 million. Gross profit was a paltry $48.7 million and losses, adjusted for inflation, added up to $85-$118 million. Nothing funny about that either.
Estimated loss: $76 – $105 million
Jack the Giant Slayer (2013)
Reviews were mixed. Critics called the film dull, lacking inspiration, and over-produced. Others found it worth the fare and “reasonably engaging” (for a kids' fantasy flick). The memorably versed narration, thundering, “Fee Fi Fo Fum!” dramatizes the olde, English fairy tale for the big screen, and the production is billed as a deeper, backstory, to the 16th-century tale about Jack and the enchanted Beanstalk.
Jack the Giant Slayer was a joint venture by Warner Bros.’ New Line division and Legendary. The fantasy adventure film was directed by Bryan Singer. Also starring, Stanley Tucci, Ian McShane, Bill Nighy, and Ewan McGregor, the story was written by Darren Lemke, who has been pitching it since 2005. The production budget rang in at an alarming $185-$200 million. And, an estimated financial loss of, wait for it…. $90 - $112 million (ouch).
Estimated loss: $86 - 106 million
Deadfall (1993)
"Deadfall" starred Michael Biehn, Charlie Sheen, James Coburn, and Peter Fonda. Its true main star, though, is none other than Nicolas Cage. Cage appeared in a few highly successful films but his career is mired with some of the worst, most unintentionally hilarious films of all time.
Nicolas Cage took the role of Eddie King in 1993's "Deadfall," a role which would proceed to be mocked for decades to come. The film was one of the worst box-office failures of all time, making a measly $18,369 against a whopping $10 million budget. It holds a 0% rating on Rotten Tomatoes and was described by film critic, Kevin Thomas as "a hopelessly callow, leaden-paced attempt at film noir." Warning — Nicolas Cage swears more in this film than in all his other roles combined.
Estimated loss: $9.9 million
Titan A.E. (2000)
This one stumbled out of the blocks with the producer and director getting canned $30 million into the production budget with little to show for it. It never fully recovered. Don Bluth and Gary Goldman, directors of Anastasia, took over from there. Alas, it was still a disaster.
According to critics, the storyline lacked originality, but the animation is a visual masterpiece, a riveting 94-minute digital canvas. The action-adventure tale takes place on a post-apocalyptic Earth, far off in the 31st century. Popular Hollywood legends Matt Damon and Drew Barrymore lend some weight to the film voicing Cale and Akima, respectively. The characters try to save the remnants of mankind left on the fantastical scorched Earth. It flopped. Box office totals for Titan A.E. were a pathetic $36.8 million dollars. It tanked locally and globally.
Estimated loss: $100 million
Gigli (2003)
We couldn't possibly make a list of the biggest box office bombs without mentioning good ol' "Gigli." Since its release, "Gigli," has topped the lists of worst films of ALL times, and there are no excuses here. It's simply a bad movie. Its production cost was $75.6 million but it grossed a subpar $7.3 million. The criticism of the movie was brutal, to say the least. The movie's title even became synonymous with failure — comedian Conan O'Brien once said "The Mets are doing so badly that they will be renamed 'The New York Gigli."
Soon after the movie's release, its lead actors, Jennifer Lopez and Ben Affleck, who had been involved romantically in real life, called it quits. Little did they know...