Drew Barrymore as Beverly Donofrio

Steve Zahn as Ray Hasek

Adam Garcia as Jason

Brittany Murphy as Fay Forrester

James Woods as Leonard Donofrio

Lorraine Bracco as Teresa Donofrio

Rosie Perez as Shirley Perro

Sara Gilbert as Tina Barr

Peter Facinelli as Tommy Butcher

Mika Boorem as Beverly Donofrio (Age 11)

Vincent Pastore as Uncle Lou

Maryann Urbano as Aunt Ann

Alexia Landeau as Jenny

Kristin Proctor as Cindy

Celine Ordioni as Janet Donofrio (Age 8)

Alissa Dean as Townie Girl #1

Jessica Leshnower as Townie Girl #2

Temple Brooks as Karen

Lauren Lake as Karen's Friend

Desmond Harrington as Bobby

Jordan Gelber as Kevin

Gabriel Carpenter as Sky Barrister

Kevin Thoms as Mark

Vincent De Paul as Linebacker

Joseph Cassese as Linebacker

Kevin O'Rourke as Jail Ward

Susan Forristal as Mrs. Forrester

John Bedford Lloyd as Mr. Forrester

Paz de la Huerta as Phone Call Flirt

Olivia Morgan Scheck as Janet Donofrio (Age 12)

David Moscow as Lizard

Dusty Rizzo as Wedding Singer Tony

Gene Canfield as Pete

Carl Capotorto as Cop #1

Robert Greenhut as Cop #2

Heather Hodder as Donofrio Cousin

Sean Liotine as Zippy

Tracy Reiner as Nurse

Joseph M. Cannizaro as Jason (Newborn)

Noah Hartwick as Jason (Newborn)

Briana Tilden as Jason (Baby)

Skye Arens as Jason (Age 1)

Patrick Salerno as Jason (Age 2)

Robert Salerno as Jason (Age 2)

Logan Arens as Jason (Age 3)

Samantha Reale as Amelia (Age 3)

Wade Mylius as Al

Jon Korkes as Counselor

Cody Arens as Jason (Age 6)

Samantha Lucier as Amelia (Age 6)

Gaetano Lisi as Sweeny's Owner

Marisa Ryan as Janet Donofrio (Age 19)

Maggie Gyllenhaal as Amelia

Logan Lerman as Jason (Age 8)

Skye McCole Bartusiak as Amelia (Age 8)

Michael Linstroth as Dennis Forrester

Sophia Barricelli as Sophia (uncredited)

Shani Bayne Haller as Waitress (uncredited)

J.D. Brookshire as Jerk in Car (uncredited)

Toni D'Antonio as Tied-Dyed Girl (uncredited)

Anna Damergis as Cop's Wife (uncredited)

Gene Gabriel as Make-Out Guy (uncredited)

Jaime Gallagher as Car Passenger (uncredited)

Donna Sue Jahier as Woman in Maternity Ward (uncredited)

Rich Keen as Passer By in Car (uncredited)

Richard Keith as Heald Family Member (uncredited)

Sara Klingebiel as Townie Girl #3 (uncredited)

Randi Rosenholtz as Townie Girl #4 (uncredited)

Peter Austin Noto as Short Order Cook (uncredited)

Dana Segal as Hippie Neighbor (uncredited)

Mario Simone as Student (uncredited)

Marilyn Spanier as Mary (uncredited)

Todd Wall as Nice Guy at Party (uncredited)

Bill Walters as Hippie at Party (uncredited)