Hank Azaria

Character: David

Kenneth Branagh

Character: Lee Simon

Judy Davis

Character: Robin Simon

Leonardo DiCaprio

Character: Brandon

Melanie Griffith

Character: Nicole Oliver

Famke Janssen

Character: Bonnie

Michael Lerner

Character: Dr. Lupus

Joe Mantegna

Character: Tony Gardella

Bebe Neuwirth

Character: Nina - the Hooker

Winona Ryder

Character: Nola

Charlize Theron

Character: Supermodel

Dylan Baker

Character: Catholic Retreat Priest

Kate Burton

Character: Robin's Friend Cheryl

Patti D'Arbanville

Character: Iris

Karen Duffy

Character: TV Reporter at Premiere

Ned Eisenberg

Character: Elaine's Book Party Guest

Monique Fowler

Character: Robin's Friend Jan

Andre Gregory

Character: John Papadakis

Allison Janney

Character: Evelyn Isaacs

Debra Messing

Character: TV Reporter

Isaac Mizrahi

Character: Bruce Bishop

Gretchen Mol

Character: Vicky

Greg Mottola

Character: Director

Larry Pine

Character: Philip Datloff

Steven Randazzo

Character: Cop at Hotel

Sam Rockwell

Character: Darrow Entourage

Aida Turturro

Character: Olga

Celia Weston

Character: Dee Bartholomew

Jeffrey Wright

Character: Greg

Carmen Dell'Orefice

Character: Pinky Virdon

Tony Sirico

Character: Lou DeMarco

Kenneth Edelson

Character: Rabbi Kaufman

Tony Darrow

Character: Moving Man in Loft

Douglas McGrath

Character: Bill Gaines

Adrian Grenier

Character: Darrow Entourage

John Doumanian

Character: Darrow Entourage

J.K. Simmons

Character: Souvenir Hawker

Donald Trump

Character: Self

Donna Hanover

Character: Manhattan Moods Anchor Woman

Leslie Shenkel

Character: Manhattan Moods Assistant Director

Wood Harris

Character: Al Swayze

Frank Pellegrino

Character: Frankie

Renée Lippin

Character: Second Examining Room Patient

Irina Pantaeva

Character: Friend of Supermodel

Mark Vanderloo

Character: Friend of Supermodel

Frederique van der Wal

Character: Friend of Supermodel

Marian Seldes

Character: Datloff Party Guest

David Margulies

Character: Counselor Adelman

Jeff Mazzola

Character: Assistant Director

Dick Mingalone

Character: Camera Operator

Vladimir Bibic

Character: Director of Photography

Francisco Quijada

Character: Erno Delucca

Aleksa Palladino

Character: Production Assistant

Dan Moran

Character: Jackhammer Operator

Peter Castellotti

Character: Sound Recordist

A. Lee Morris

Character: Second Assistant Cameraperson

Maurice Sonnenberg

Character: Dalton Freed

Craig Ulmschneider

Character: Production Assistant Daniel

Mina Bern

Character: Elderly Homeowner

Janet Marlow

Character: Singing Nun

Tommie Baxter

Character: Second Nun

Kathleen Doyle

Character: Father Gladden's Fan

Arthur Berwick

Character: Father Gladden's Fan

Jodi Long

Character: Father Gladden's Fan

John Carter

Character: Father Gladden

Marylouise Burke

Character: Father Gladden's Fan on Porch

Peter Boyden

Character: Father Gladden's Fan on Porch

Peter McRobbie

Character: Father Gladden's Fan on Porch

Maureen McNamara

Character: Father Gladden's Fan on Porch

Mary Catherine Wright

Character: Pious Diner

Melinda Eng

Character: Fashion Designer

Alma Cuervo

Character: Bruce Bishop's Admirer

Ève Salvail

Character: Bruce Bishop's Admirer

Polly Adams

Character: Exercise Tape Fan

Brian McConnachie

Character: Exercise Tape Fan

Anthony Mason

Character: Himself

Daisy Prince

Character: Waiting Room Nurse

Tina Sloan

Character: Waiting Room Patient

Dayle Haddon

Character: Waiting Room Patient

Bill Gerber

Character: Waiting Room Patient

Julie Halston

Character: Patient With Jowls

Reuben Jackson

Character: Cameraman at Lupus Office

Skip Rose

Character: Couple on Beach

Alicia Meer

Character: Couple on Beach

Becky Ann Baker

Character: Glenwood High Alumna - Doris

Michael Kell

Character: Glenwood High Alumna - Nat

Steve Mellor

Character: Glenwood High Alumna - Eddie

Gerry Becker

Character: Glenwood High Alumna - Jay Tepper

Ileen Getz

Character: Glenwood High Alumna - Reunion Announcer

Robert Cuccioli

Character: Glenwood High Alumna - Monroe Gordon

Surinder Khosla

Character: V.J. Rajnipal

Frederick Rolf

Character: Book Reviewer

Ramsey Faragallah

Character: TV Program Director

William Addy

Character: Klansman

Patrick Thomas McCarthy

Character: Klansman

Bernard Addison

Character: Minister Polynice

Mary Samuels

Character: TV Production Assistant

Sarah Buff

Character: TV Production Assistant

Heather Marni

Character: Teenage Obese Acrobat

Bruno Gunn

Character: Skinhead

Sean Daloise

Character: Skinhead

Matthew Sweeney

Character: Skinhead

Kyle Kulish

Character: Overweight Achiever

Sam Gray

Character: Tony's Father

Marilyn Raphael

Character: Tony's Mother

Antonette Schwartzberg

Character: Tony's Grandma

Gabriel Millman

Character: Ricky

Adam Sietz

Character: Vince

Michael Crecco

Character: Hotel Clerk

Neal Arluck

Character: Hotel Clerk

Timothy Jerome

Character: Hotel Clerk

Joseph Tudisco

Character: Hotel Clerk

Jim Moody

Character: Security Guard

Robert Torres

Character: Security Guard

John Costelloe

Character: Cop at Hotel

Mary Jo Buttafuoco

Character: Herself

Joey Buttafuoco

Character: Himself

Lorri Bagley

Character: Chekhov-style Writer

Richard Mawe

Character: Elaine's Book Party Guest

Ted Neustadt

Character: Elaine's Book Party Guest

Bruce Jay Friedman

Character: Elaine's Book Party Guest

Erica Jong

Character: Elaine's Book Party Guest

Clebert Ford

Character: Elaine's Book Party Guest

Ralph Pope

Character: Comic's Agent

Rick Mowat

Character: Comic

Victor Colicchio

Character: Moving Man in Loft

Robert Cividanes

Character: Moving Man in Loft

Donegal Fitzgerald

Character: Moving Man on Street

Howard Erskine

Character: Senator Paley

Ray Cohen

Character: Pianist at Wedding

Angel Caban

Character: Limo Driver

Ingrid Rogers

Character: Off-Off Broadway Actress

Brian McCormack

Character: Phil

Gigi Williams

Character: Fan of Robin Simon

Laura Nativo

Character: Jailbait (uncredited)