Adam Sandler as Longfellow Deeds

Winona Ryder as Babe Bennett

John Turturro as Emilio Lopez

Allen Covert as Marty

Peter Gallagher as Chuck Cedar

Jared Harris as Mac McGrath

Erick Avari as Cecil Anderson

Peter Dante as Murph

Conchata Ferrell as Jan

Harve Presnell as Preston Blake

Steve Buscemi as Crazy Eyes

Blake Clark as Buddy Ward

John McEnroe as John McEnroe

JB Smoove as Reuben

Tom McNulty as Red Parka Man

Buddy Bolton as Cameraman

Angelito Bautista as Sherpa

Scott Thompson Baker as News Anchor

Robert Frank Telfer as Business Anchor

Elizabeth Owens as Kitty - Bench Woman

Florence Anglin as Jane - Bench Woman

Sylvia Kauders as Sue - Bench Woman

Henry Hayward as Mr. Wetherley

Frank Weller as Old Farmer

Karen Nation as Lucy

Bruce French as Helicopter Pilot

Ken Forsgren as Co-Pilot

Earl Schuman as Blake's Valet

Marijan 'Mario' Zoric as Blake's Chef

Irina Davidoff as Blake's Russian Maid

William Brady as Chauffeur

Brandon Molale as Kevin Ward

Derek Hughes as Waiter

Walter Williamson as Kurt

Roark Critchlow as William

Billy St. John as George

Kevin Grady as Anniversary Couple

Dru Homer as Anniversary Couple

Frank Montella as Bishop

Alfred Dennis as Old-Timer

Margie Loomis as Martha

Alex Buck as Gum Chewer

Tyler Roche as Young Kid

Lauren Mieske as Little Sister

Steele Hunter as Children's Father

George Wallace as NAACP Administrator

Gabriel Williams as Mailroom Clerk

Dianne Crawford as Secretary

John Kirk as Bartender

Aloma Wright as Coretta Keeling - Cat Lady

J.D. Donaruma as Fake Cop

Carter Edwards as Yelling Cop

Steven James Golebiowski as Yelling Fireman

Tim Herlihy as Fireman

Chloé Hult as Waitress

Sidney Ganis as Homeless Man (as Sid Ganis)

Randolph LeRoi as Afro Man

Jeremy Chu as Bike-Riding Kid

Gideon Jacobs as Bike-Riding Kid

Craig 'Radio Man' Castaldo as Radioman

Gina Gallego as Consuela Lopez

Al Sharpton as The Rhyme Master

Dion Anderson as Shareholder

Susan Bjurman as Shareholder

Andy Kreiss as Shareholder

Ramesh Pandey as Shareholder

Maurice G. Smith as Shareholder

Jennifer Tisdale as Card Reader

Toshi Toda as Card Reader

Rob Schneider as Nazo the Italian Delivery Man (uncredited)

Steve C. Porter as Pvt. James Dailey (uncredited)