Adam Sandler

as Dave Buznik

Jack Nicholson

as Dr. Buddy Rydell

Marisa Tomei

as Linda

Luis Guzmán

as Lou

Allen Covert

as Andrew

Lynne Thigpen

as Judge Daniels

Kurt Fuller

as Frank Head

Jonathan Loughran

as Nate

Krista Allen

as Stacy

January Jones

as Gina

Woody Harrelson

as Galaxia / Security Guard Gary

John Turturro

as Chuck

Kevin Nealon

as Sam

Conrad Goode

as Bailiff / Lexus Man

Gina Gallego

as Bar Waitress

Nancy Carell

as Flight Attendant

Marisa Chandler

as Flight Attendant

Don Diamont

as Man in Seat

Isaac C. Singleton, Jr.

as Air Marshall

Bobby Knight

as Bobby Knight

John McEnroe

as John McEnroe

Rudolph Giuliani

as Mayor Rudy Giuliani

Judith Nathan

as Judith Nathan

Tony Carbonetti

as Tony Carbonetti

Bob Sheppard

as The Voice of the Yankees

Robert Merrill

as Robert Merrill

Derek Jeter

as Derek Jeter

Lori Heuring

as Anger Management Receptionist

Stephen Dunham

as Maitre d'

Jeff Morris

as Porter

Tony Genaro

as Cabbie

John Kirk

as Bar Waitress's Lawyer

Ken Rosier

as Buddy's Lawyer

Clint Black

as Masseur

Rob Steiner

as Dave's Co-Worker

Lorna Scott

as Lady in Restroom

Bonnie Hellman

as Wife at Table

Joe Howard

as Husband at Table

Kevin Dunigan

as Man #1 in Anger Group

Paul Renteria

as Man #2 in Anger Group

Kevin Grady

as Baseball Fan

Sidney Ganis

as Neighbor

Larry Morgan

as Pool Player

Cody Arens

as Boy at Yankee Stadium

Michael Arthur

as Police Officer

Jonathan Osser

as Young Dave Buznik

Melissa Mitchell

as Sara

Alan James Morgan

as Young Arnie Shankman

Lindsey Weber

as Arnie's Sister

Halley Eveland

as Wedgie Boy

Taylor Segal

as Laughing Girl

Nikki Segal

as Girl Playing in Water

John C. Reilly

as Older Arnie Shankman (uncredited)

Harry Dean Stanton

as Blind Man (uncredited)

Heather Graham

as Kendra (uncredited)

Kristen Moser

as Lauren (uncredited)

Dawn Drake

as Girl on Plane (uncredited)

Sarah Beth Nelson

as Kelly Canfield (uncredited)

Nils Allen Stewart

as Tiny (uncredited)

Tom Malloy

as Yankees Left Fielder (uncredited)

Zack Abramowitz

as Baseball Fan (uncredited)

Arnold Chon

as Buddhist Monk (uncredited)

John Farrer

as Yankees Fan (uncredited)