Adam Sandler

Character: Longfellow Deeds

Winona Ryder

Character: Babe Bennett

John Turturro

Character: Emilio Lopez

Allen Covert

Character: Marty

Peter Gallagher

Character: Chuck Cedar

Jared Harris

Character: Mac McGrath

Erick Avari

Character: Cecil Anderson

Peter Dante

Character: Murph

Conchata Ferrell

Character: Jan

Harve Presnell

Character: Preston Blake

Steve Buscemi

Character: Crazy Eyes

Blake Clark

Character: Buddy Ward

John McEnroe

Character: John McEnroe

JB Smoove

Character: Reuben

Tom McNulty

Character: Red Parka Man

Buddy Bolton

Character: Cameraman

Angelito Bautista

Character: Sherpa

Scott Thompson Baker

Character: News Anchor

Robert Frank Telfer

Character: Business Anchor

Elizabeth Owens

Character: Kitty - Bench Woman

Florence Anglin

Character: Jane - Bench Woman

Sylvia Kauders

Character: Sue - Bench Woman

Henry Hayward

Character: Mr. Wetherley

Frank Weller

Character: Old Farmer

Karen Nation

Character: Lucy

Bruce French

Character: Helicopter Pilot

Ken Forsgren

Character: Co-Pilot

Earl Schuman

Character: Blake's Valet

Marijan 'Mario' Zoric

Character: Blake's Chef

Irina Davidoff

Character: Blake's Russian Maid

William Brady

Character: Chauffeur

Brandon Molale

Character: Kevin Ward

Derek Hughes

Character: Waiter

Walter Williamson

Character: Kurt

Roark Critchlow

Character: William

Billy St. John

Character: George

Kevin Grady

Character: Anniversary Couple

Dru Homer

Character: Anniversary Couple

Frank Montella

Character: Bishop

Alfred Dennis

Character: Old-Timer

Margie Loomis

Character: Martha

Alex Buck

Character: Gum Chewer

Tyler Roche

Character: Young Kid

Lauren Mieske

Character: Little Sister

Steele Hunter

Character: Children's Father

George Wallace

Character: NAACP Administrator

Gabriel Williams

Character: Mailroom Clerk

Dianne Crawford

Character: Secretary

John Kirk

Character: Bartender

Aloma Wright

Character: Coretta Keeling - Cat Lady

J.D. Donaruma

Character: Fake Cop

Carter Edwards

Character: Yelling Cop

Steven James Golebiowski

Character: Yelling Fireman

Tim Herlihy

Character: Fireman

Chloé Hult

Character: Waitress

Sidney Ganis

Character: Homeless Man (as Sid Ganis)

Randolph LeRoi

Character: Afro Man

Jeremy Chu

Character: Bike-Riding Kid

Gideon Jacobs

Character: Bike-Riding Kid

Craig 'Radio Man' Castaldo

Character: Radioman

Gina Gallego

Character: Consuela Lopez

Al Sharpton

Character: The Rhyme Master

Dion Anderson

Character: Shareholder

Susan Bjurman

Character: Shareholder

Andy Kreiss

Character: Shareholder

Ramesh Pandey

Character: Shareholder

Maurice G. Smith

Character: Shareholder

Jennifer Tisdale

Character: Card Reader

Toshi Toda

Character: Card Reader

Rob Schneider

Character: Nazo the Italian Delivery Man (uncredited)

Steve C. Porter

Character: Pvt. James Dailey (uncredited)