David Spade as Dickie Roberts

Mary McCormack as Grace Finney

Jon Lovitz as Sidney Wernick

Craig Bierko as George Finney

Alyssa Milano as Cyndi

Rob Reiner as Self

Scott Terra as Sam Finney

Jenna Boyd as Sally Finney

John Farley as Referee

Michael Buffer as Self

Spencer Garrett as Publisher

Rachel Dratch as Reiner's Secretary

Bobby Slayton as Commentator

Fred Wolf as Dickie's Corner Man

Emmanuel Lewis as Self

Joey Diaz as Emmanuel's Entourage

Kevin Grevioux as Emmanuel's Entourage

Brian Clark as Guy in Car

Leif Garrett as Himself

Emily Harrison as Girl

Nancy M. Pimental as Girl

Alan Blumenfeld as Mr. Rollins

Sasha Mitchell as Angry Driver

M. Blair Breard as Alcoholic Speaker

Tom Arnold as Self

Kathleen Randazzo as Counselor

Peggy Mannix as Lamaze Group Leader

Corey Feldman as Self

Barry Williams as Self

Danny Bonaduce as Self

Dustin Diamond as Self

Hal Sparks as Publisher

Rob Elk as Biker

Retta as Sad Eye Sadie

Ian Gomez as Strange Man

Doris Roberts as Peggy Roberts

Dick Van Patten as Self

Nicholas Schwerin as Young Dickie

Michelle Ruben as Ring Girl

Edie McClurg as Mrs. Gertrude

John Kirk as Passing Man with Camera

Alexander D. Slanger as Map Seller

Oliver Kindred as Bully

Brandon de Paul as Bully

Evan Lee Dahl as Bully

Wyatt Smith as Boy in Crowd

Patrick Thomas O'Brien as Mr. Gertrude

Colin Ryan as Gertrude Kid

Christopher Johnson as Boy

Sergei Virovlianski as Boy

Jake Chapman as Boy

Ambyr Childers as Barbie

Valerie Perrine as Teacher at Microphone

Ashley Edner as Heather Bolan

Kevin Farley as Valet

Miko C. Brando as Valet

Mindy Burbano as News Correspondent

Jann Carl as Self

Lindsey Dann as Reporter

Lisa Joyner as Self

Erin Murphy as Brittany

Meghan Faye Gallagher as Janice

Willie Aames as Self

Fred Berry as Self

Todd Bridges as Self

Gary Coleman as Self

Jeff Conaway as Self

Corey Haim as Self

Tony Dow as Self

Florence Henderson as Self

Christopher Knight as Self

Barry Livingston as Self

Mike Lookinland as Self

Maureen McCormick as Self

Eddie Mekka as Self

Jeremy Miller as Self

Erin Moran as Self

Haywood Nelson as Self

Jay North as Self

Ron Palillo as Self

Butch Patrick as Self

Jonathan Loughran as Self

Peter Dante as Self

Paul Petersen as Self

Adam Rich as Self

Rodney Allen Rippy as Self

Marion Ross as Self

Ernest Lee Thomas as Self

Charlene Tilton as Self

Michael McDonald as Maitre' D

Brendan Fraser as Self (uncredited)

Jesse Rutherford as 5th Grade Boy