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.
Kevin Hart plays the role of Darnell--a family man desperate to get enough money to buy a house in a better area to benefit his family's well-being. He is hired by James (Will Ferrell), a wimpy stock trader who is about to go to prison for 10 years, to prepare him for life behind bars. The catch is that James thinks Darnell is an ex-con--not because Darnell told him that, but because James just assumed.