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)