Jack Nicholson

Melvin Udall

Helen Hunt

Carol Connelly

Greg Kinnear

Simon Bishop

Cuba Gooding Jr.

Frank Sachs

Shirley Knight

Beverly Connelly

Jesse James

Spencer Connelly

Yeardley Smith

Jackie Simpson

Lupe Ontiveros

Nora Manning

Skeet Ulrich

Vincent Lopiano

Harold Ramis

Dr. Bettes

Lawrence Kasdan

Dr. Green

Bibi Osterwald

Neighbor Woman

Ross Bleckner

Carl

Bernadette Balagtas

Caterer

Jaffe Cohen

Partygoer

Laurie Kilpatrick

Partygoer

Alice Vaughn

Partygoer

Brian Doyle-Murray

Handyman

Kristi Zea

Mother at Table

Annie Maginnis Tippe

Daughter at Table

Patricia Childress

Cafe 24 Waitress

Rebekah Johnson

Cafe 24 Waitress

Missi Pyle

Cafe 24 Waitress

Leslie Stefanson

Cafe 24 Waitress

Tara Subkoff

Cafe 24 Waitress

Shane Black

Cafe 24 Manager

Peter Jacobson

Man at Table

Lisa Edelstein

Woman at Table

Stan Bly

Cafe 24 Customer

Randall Batinkoff

Carol's Date

Jamie Kennedy

Street Hustler

Justin Herwick

Street Hustler

Maya Rudolph

Policewoman

John F. O'Donohue

Detective Ray

Dr. David A. Kipper

Hospital Doctor

Mary Elizabeth Still

Nurse Receptionist

Chloe Brooks

Child at Cafe 24

Cooper Brooks

Child at Cafe 24

Sharon L. Alexander

Female Passerby

Holly Denys

Female Passerby

Alison Rose

Psychiatric Patient

Kathryn Morris

Psychiatric Patient

Wood Harris

Cafe 24 Busboy

Linda Gehringer

Publisher

Julie Benz

Receptionist

Antonia Jones

Nurse

Kaitlin Hopkins

Woman in Lobby

Jimmy Workman

Sean from the Bakery

Danielle Spencer

Veterinarian

Todd Solondz

Man on Bus

Tom McGowan

Maitre'd

Danielle Brisebois

Singer

Matt Malloy

Men's Store Salesman

Paul Greenberg

Bar Waiter

Kirk Ringberg

Food Waiter

Dave Hawthorne

Bartender

Dunya Djordjevic

Art Dealer (uncredited)

Alex Ballar

Flower Store Customer (uncredited)

Jason Thomas Campbell

Valet (uncredited)

Amy Anzel

Ballet Dancer (uncredited)

Eliza Harris

Ballet Dancer (uncredited)

Eddie L. Fauria

NYC Transit Cop (uncredited)

Frank Slaten

Miffed Party Goer (uncredited)

Laura Mayes Byrnes

Restaurant Patron (uncredited)

Oriana Nicole Tavoularis

Restaurant Patron (uncredited)

Roger Ferreira

Restaurant Patron (uncredited)

Bronwyn Cornelius

Bartender (uncredited)

Maurice LaMarche

Fred Bishop - Simon's Dad on Phone (voice) (uncredited)

Ava Lee Scott

New Yorker