Fantastic Four – $100 million
What did deserve to flop, and did flop in extraordinary fashion, is Fantastic Four. If you don’t remember, Marvel made Fantastic Four starring Chris Evans as the Human Torch and a cast of unmemorable actors. Thankfully, Chris got the heck out of FF and took up the role of Captain America where he truly belongs.

Following the success of Spider-Man and Spider-Man 2, people had pretty high expectations for what Marvel would do next. It turns out Marvel’s next plan was to disappoint its fan base with a movie that would go on to lose $100 million. And then they made a sequel, Rise of the Silver Surfer, two years later, which was bad but at least made money.