Diane Keaton

Bridget Cardigan

Queen Latifah

Nina Brewster

Katie Holmes

Jackie Truman

Ted Danson

Don Cardigan

Adam Rothenberg

Bob Truman

Roger Cross

Barry

Stephen Root

Glover

J.C. MacKenzie

Richard Mandelbrot

Christopher McDonald

Bryce Arbogast

Meagen Fay

Mindy Arbogast

Finesse Mitchell

Shaun

Mathew Greer

Junior

Peyton Alex Smith

Older Dante

Morgana Shaw

Molly

Marc Macaulay

Agent Wayne

Andrew Sensenig

Cart Guy

Jim Cramer

Self

Michael P. Flannigan

Foreman

Drew Waters

Fed Guy #1

Ginnie Randall

Ms. Cobb

Cliff Fleming

Helicopter Pilot

Clay Chamberlin

Waiter

Bryan Massey

Detective Brinkley

Sterling Blackmon

Older Jimmy

Jimmy Lee Jr.

Federal Reserve Officer (uncredited)

Michael Showers

Detective (uncredited)