Get Hard (2015)

When a rich hedge-fund manager, James, 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 turns to Darnell, 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.