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6. Town & Country (2001)

Net losses, inflation adjusted: $115,352,672
Total cost: $105,000,000
Worldwide theater gross: $10,372,291
Net losses (actual): $94,627,709

Town & Country was a 2001 ensemble comedy starring Warren Beatty, Goldie Hawn, Diane Keaton and Garry Shandling. Ensemble comedies are relatively inexpensive to make, as there’s no CGI or full-scale replicas of the Titanic to pay for.

But Beatty demanded a huge number of takes for each scene, and the script was still being re-written as the movie was shooting, pushing the production behind schedule. Shandling and Keaton both had to leave the shoot before it was finished in order to do other films, and it would be a year before the cast reunited to finish it.

Three years after filming began the movie was released, receiving severe thrashings from critics and audiences alike. Ultimately it lost close to $100 million, making it one of the most unsuccessful movies of all time.

Photo: New Line Cinema