Synopsis
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.
Cast

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
More like this

Bringing Down the House

Big Stan

Stir Crazy

That's My Boy

Madea's Witness Protection

I Love You Phillip Morris

Bandits

Analyze That

The Longest Yard

Tough Guys

The Letter Room

The Wolf of Wall Street

The Boss

Married to the Mob

Oscar

The Big Short

Fun with Dick and Jane

Hustlers

The Valet

Dumb Money