25 Great Movies That Flopped

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22. How Do You Know (2010)

Reese Witherspoon, Paul Rudd, Owen Wilson, and Jack Nicholson teamed up to create the quirky and fun romantic comedy “How Do You Know”.

Though the film was a feel-good story, it fell flat at the box office.

The basic premise of the film is that Paul Rudd’s character George Madison was kicked out of his dad’s company and is trying to figure out what to do with his life.

On the same day Witherspoon’s character, a professional softball player, finds out she was left off the Olympic team. The two meet up in an elevator by coincidence and soon develop a friendship and then a relationship.

However, things are complicated for Rudd’s character when he finds out that Witherspoon is also being wooed by Wilson’s character, a sleazy, less-than-kind man that Rudd feels Witherspoon is far too good for.

Life is further complicated for Rudd’s character when he discovers he is the subject of a federal investigation, and later finds out that his dad, played by Jack Nicholson, had set him up to take the fall because Rudd would face less prison time than Nicholson.

At the end Rudd asks if his father will give him one last chance to convince Witherspoon to be with him, making the deal that if she says no he’ll go to prison for his father, but if she says yes his father must do the time. Fortunately, Witherspoon goes for Rudd and his father gets his due justice.

Most people who saw the film loved it, and even the critics weren’t unduly harsh. Many blame the $75.6 million box office loss on the proximity of the film’s release to Christmas, slating that some of the more impressive and more highly anticipated films posed nearly unbeatable competition for the romantic comedy.