Adam Sandler

Longfellow Deeds

Winona Ryder

Babe Bennett

John Turturro

Emilio Lopez

Allen Covert

Marty

Peter Gallagher

Chuck Cedar

Jared Harris

Mac McGrath

Erick Avari

Cecil Anderson

Peter Dante

Murph

Conchata Ferrell

Jan

Harve Presnell

Preston Blake

Steve Buscemi

Crazy Eyes

Blake Clark

Buddy Ward

John McEnroe

John McEnroe

JB Smoove

Reuben

Tom McNulty

Red Parka Man

Buddy Bolton

Cameraman

Angelito Bautista

Sherpa

Scott Thompson Baker

News Anchor

Robert Frank Telfer

Business Anchor

Elizabeth Owens

Kitty - Bench Woman

Florence Anglin

Jane - Bench Woman

Sylvia Kauders

Sue - Bench Woman

Henry Hayward

Mr. Wetherley

Frank Weller

Old Farmer

Karen Nation

Lucy

Bruce French

Helicopter Pilot

Ken Forsgren

Co-Pilot

Earl Schuman

Blake's Valet

Marijan 'Mario' Zoric

Blake's Chef

Irina Davidoff

Blake's Russian Maid

William Brady

Chauffeur

Brandon Molale

Kevin Ward

Derek Hughes

Waiter

Walter Williamson

Kurt

Roark Critchlow

William

Billy St. John

George

Kevin Grady

Anniversary Couple

Dru Homer

Anniversary Couple

Frank Montella

Bishop

Alfred Dennis

Old-Timer

Margie Loomis

Martha

Alex Buck

Gum Chewer

Tyler Roche

Young Kid

Lauren Mieske

Little Sister

Steele Hunter

Children's Father

George Wallace

NAACP Administrator

Gabriel Williams

Mailroom Clerk

Dianne Crawford

Secretary

John Kirk

Bartender

Aloma Wright

Coretta Keeling - Cat Lady

J.D. Donaruma

Fake Cop

Carter Edwards

Yelling Cop

Steven James Golebiowski

Yelling Fireman

Tim Herlihy

Fireman

Chloé Hult

Waitress

Sidney Ganis

Homeless Man (as Sid Ganis)

Randolph LeRoi

Afro Man

Jeremy Chu

Bike-Riding Kid

Gideon Jacobs

Bike-Riding Kid

Craig Castaldo

Radioman

Gina Gallego

Consuela Lopez

Al Sharpton

The Rhyme Master

Dion Anderson

Shareholder

Susan Bjurman

Shareholder

Andy Kreiss

Shareholder

Ramesh Pandey

Shareholder

Maurice G. Smith

Shareholder

Jennifer Tisdale

Card Reader

Toshi Toda

Card Reader

Rob Schneider

Nazo the Italian Delivery Man (uncredited)

Steve C. Porter

Pvt. James Dailey (uncredited)