Get Hard (2015)

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.