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When obscenely rich hedge-fund manager James (Will Ferrell) is convicted of fraud and sentenced to a stretch in San Quentin, the judge gives him one month to get his affairs in order. Knowing that he won't survive more than a few minutes in prison on his own, James desperately turns to Darnell (Kevin Hart) -- a black businessman who's never even had a parking ticket -- for help. As Darnell puts James through the wringer, both learn that they were wrong about many things, including each other.