When millionaire 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 desperately 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.
Will Ferrell
James King
Kevin Hart
Darnell Lewis
Alison Brie
Alissa
Craig T. Nelson
Martin
T.I.
Russell
Greg Germann
Peter Penny
Matt Walsh
Bathroom Stall Man
Mariana Paola Vicente
Alissa's Friend
Katia Gomez
Rosa
Candi Brooks
Alissa's Friend
Jimmy Fallon
Jimmy Fallon
Edwina Findley
Rita
Erick Chavarria
Cecelio
Ariana Neal
Makayla
Paul Ben-Victor
Gayle Burns
John Mayer
John Mayer
Jon Eyez
Big Mike
Nito Larioza
Jaoa
Dan Bakkedahl
Leo
Ron Funches
Jojo
Jackie Tuttle
Alissa's Friend
Christopher Berry
Spider
Raeden Greer
Groupie
Elliott Grey
Judge V. Carlyle
James Moses Black
FBI Agent
Brian Oerly
Skinhead
Chris Marroy
Trader
Joshua Joseph Gillum
Rico
Dave Davis
Cross Dresser
T.J. Jagodowski
Chris
Shad Gaspard
Big Ass Julian
Dominique Perry
Shonda
Eli Jane
Yoga Mom (uncredited)
Erika Erica
Client (uncredited)
Hans Marrero
Big Guy #3 (uncredited)
Michael Martin
Homeless Guy
Jason R.A. Foster
Car washer
Michael P. Sullivan
Guy In Crowd
Community
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