The Kid

Bruce Willis

Russ Duritz

Spencer Breslin

Rusty Duritz

Emily Mortimer

Amy

Lily Tomlin

Janet

Jean Smart

Deirdre Lefever

Chi McBride

Kenny

Daniel von Bargen

Sam Duritz

Dana Ivey

Dr. Alexander

Stanley Anderson

Bob Riley

Juanita Moore

Kenny's Grandmother

Susan Dalian

Giselle

Esther Scott

Clarissa

Deborah May

Governor

Vernee Watson

Newsstand Cashier

Jan Hoag

Newsstand Tourist

Melissa McCarthy

Sky King Waitress

Elizabeth Arlen

Gloria Duritz

Alexandra Barreto

Flight Attendant

John Apicella

Hot Dog Vendor

Brian McGregor

Vince

Reiley McClendon

Mark

Brian Tibbetts

Herbert

Brian McLaughlin

George

Steve Tom

Lawyer Bruce

Marc Copage

Lawyer Jim

Rod McLachlan

Lawyer Seamus

Scott Mosenson

Wedding Guest

Brian Fenwick

Governor's Aide

Duke Faeger

Governor's Other Aide

Toshiya Agata

Sushi Chef

Joshua Finkel

Josh

Lou Beatty Jr.

General Manager

E.J. Callahan

Principal

Daryl Anderson

Janet's Husband

Darrell Foster

Best Man

Michael Wajacs

Security Guard

John Travis

Chef Mike

Larry King

Larry King

Jeri Ryan

Larry King's Guest

Nick Chinlund

Larry King's Guest

Stuart Scott

Ritch Eisen

Rich Eisen

Stuart Scott

Kevon Edmonds

Wedding Singer

Julia Waters

Backup Singer

Maxine Waters Willard

Backup Singer

Stephanie Spruill

Backup Singer

Tanisha Grant

Bridesmaid (uncredited)

Viola Odette Harlow

(uncredited)

Paul Moncrief

Car Driver (uncredited)

Matthew Perry

Mr. Vivian (uncredited)

Luigi Francis Shorty Rossi

Tim (uncredited)

Gary Weeks

Russ' Son (uncredited)

Harold Greene

Harold Greene