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 Bibi Osterwald Neighbor Woman Ross Bleckner Carl Bernadette Balagtas Caterer 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 Randall Batinkoff Carol's Date Jamie Kennedy Street Hustler Maya Rudolph Policewoman Lawrence Kasdan Dr. Green Alison Rose Psychiatric Patient Kathryn Morris Psychiatric Patient Wood Harris Cafe 24 Busboy Linda Gehringer Publisher Julie Benz Receptionist Antonia Jones Nurse Jimmy Workman Sean from the Bakery Matt Malloy Men's Store Salesman Maurice LaMarche Fred Bishop - Simon's Dad on Phone (voice) (uncredited)