Adam Sandler

Dave Buznik

Jack Nicholson

Dr. Buddy Rydell

Marisa Tomei

Linda

Luis Guzmán

Lou

Allen Covert

Andrew

Lynne Thigpen

Judge Daniels

Kurt Fuller

Frank Head

Jonathan Loughran

Nate

Krista Allen

Stacy

January Jones

Gina

Woody Harrelson

Galaxia / Security Guard Gary

John Turturro

Chuck

Kevin Nealon

Sam

Conrad Goode

Bailiff / Lexus Man

Gina Gallego

Bar Waitress

Nancy Carell

Flight Attendant

Marisa Chandler

Flight Attendant

Don Diamont

Man in Seat

Isaac C. Singleton, Jr.

Air Marshall

Bobby Knight

Bobby Knight

John McEnroe

John McEnroe

Rudolph Giuliani

Mayor Rudy Giuliani

Judith Nathan

Judith Nathan

Tony Carbonetti

Tony Carbonetti

Bob Sheppard

The Voice of the Yankees

Robert Merrill

Robert Merrill

Derek Jeter

Derek Jeter

Lori Heuring

Anger Management Receptionist

Stephen Dunham

Maitre d'

Jeff Morris

Porter

Tony Genaro

Cabbie

John Kirk

Bar Waitress's Lawyer

Ken Rosier

Buddy's Lawyer

Clint Black

Masseur

Rob Steiner

Dave's Co-Worker

Lorna Scott

Lady in Restroom

Bonnie Hellman

Wife at Table

Joe Howard

Husband at Table

Kevin Dunigan

Man #1 in Anger Group

Paul Renteria

Man #2 in Anger Group

Kevin Grady

Baseball Fan

Sidney Ganis

Neighbor

Larry Morgan

Pool Player

Cody Arens

Boy at Yankee Stadium

Michael Arthur

Police Officer

Jonathan Osser

Young Dave Buznik

Melissa Mitchell

Sara

Alan James Morgan

Young Arnie Shankman

Lindsey Weber

Arnie's Sister

Halley Eveland

Wedgie Boy

Taylor Segal

Laughing Girl

Nikki Segal

Girl Playing in Water

John C. Reilly

Older Arnie Shankman (uncredited)

Harry Dean Stanton

Blind Man (uncredited)

Heather Graham

Kendra (uncredited)

Kristen Moser

Lauren (uncredited)

Dawn Drake

Girl on Plane (uncredited)

Sarah Beth Nelson

Kelly Canfield (uncredited)

Nils Allen Stewart

Tiny (uncredited)

Tom Malloy

Yankees Left Fielder (uncredited)

Zack Abramowitz

Baseball Fan (uncredited)

Arnold Chon

Buddhist Monk (uncredited)

John Farrer

Yankees Fan (uncredited)