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13. 'How Do You Know'

How Do You Know seemed like a good idea, right? Take two Oscar winners in Reese Witherspoon and Jack Nicholson, pair them with likable everymen Paul Rudd and Owen Wilson, and let them all work with an Oscar winning director. The problem with getting all these top-notch names is that you have to pay them top-notch salaries, which doomed this rom-com. The film suffered huge losses at the box office, grossing only 40 percent of its $120 million budget back.