Bridget Cardigan

Diane Keaton

Nina Brewster

Queen Latifah

Jackie

Katie Holmes

Don Cardigan

Ted Danson

Barry

Roger R. Cross

Bob Truman

Adam Rothenberg

Barry

Roger Cross

Glover

Stephen Root

Older Jimmy

Sterling Blackmon

Older Dante

Peyton Smith

Richard Mandelbrot

J.C. MacKenzie

Bryce Arbogast

Christopher McDonald

Cop No. 1

Charlie Caldwell

Shaun

Finesse Mitchell

Cop No. 2

Richard F. Law

Molly

Morgana Shaw

Mindy Arbogast

Meagen Fay

Junior

Mathew Greer

Older Dante

Peyton Alex Smith

Counselor

Denise Lee

Selina

Sylvia Castro Galan

Agent Wayne

Marc Macaulay

Cart Guy

Andrew Sensenig

Young Dante

Maliek Golden

Young Jimmy

Khari King

Himself

Jim Cramer

Headmaster

John McIntosh

Jeweler

Bill Jenkins

Foreman

Michael P. Flannigan

Fed Guy No. 1

Drew Waters

Fed Guy No. 2

Tron Kendrick

Ms. Cobb

Ginnie Randall

Detective Smith

Joe Nemmers

Detective Jones

Julius Washington

Helicopter Pilot

Cliff Fleming

Hotel Clerk

Jennifer Wilkerson

District Attorney

Bryan McMahon

IRS Man

Richard Folmer

Detective Scott

Duke W. Scott Jr.

Waiter

Clay Chamberlin

Detective Brinkley

Bryan Massey

Queen

Girl Scout (uncredited)

Cassidy Smith

Callie

Federal Reserve Officer (uncredited)

Jimmy Lee Jr.

Agent (uncredited)

Deborah R. Jones

Detective Jones

Julius Gregory

Detective (uncredited)

Michael Showers

Cop (uncredited)

Bill Stinchcomb