Celebrity

Hank Azaria

As David

Kenneth Branagh

As Lee Simon

Judy Davis

As Robin Simon

Leonardo DiCaprio

As Brandon

Melanie Griffith

As Nicole Oliver

Famke Janssen

As Bonnie

Michael Lerner

As Dr. Lupus

Joe Mantegna

As Tony Gardella

Bebe Neuwirth

As Nina - the Hooker

Winona Ryder

As Nola

Charlize Theron

As Supermodel

Dylan Baker

As Catholic Retreat Priest

Kate Burton

As Robin's Friend Cheryl

Patti D'Arbanville

As Iris

Karen Duffy

As TV Reporter at Premiere

Ned Eisenberg

As Elaine's Book Party Guest

Monique Fowler

As Robin's Friend Jan

Andre Gregory

As John Papadakis

Allison Janney

As Evelyn Isaacs

Debra Messing

As TV Reporter

Isaac Mizrahi

As Bruce Bishop

Gretchen Mol

As Vicky

Greg Mottola

As Director

Larry Pine

As Philip Datloff

Steven Randazzo

As Cop at Hotel

Sam Rockwell

As Darrow Entourage

Aida Turturro

As Olga

Celia Weston

As Dee Bartholomew

Jeffrey Wright

As Greg

Carmen Dell'Orefice

As Pinky Virdon

Tony Sirico

As Lou DeMarco

Kenneth Edelson

As Rabbi Kaufman

Tony Darrow

As Moving Man in Loft

Douglas McGrath

As Bill Gaines

Adrian Grenier

As Darrow Entourage

John Doumanian

As Darrow Entourage

J.K. Simmons

As Souvenir Hawker

Donald Trump

As Self

Donna Hanover

As Manhattan Moods Anchor Woman

Leslie Shenkel

As Manhattan Moods Assistant Director

Wood Harris

As Al Swayze

Frank Pellegrino

As Frankie

Renée Lippin

As Second Examining Room Patient

Irina Pantaeva

As Friend of Supermodel

Mark Vanderloo

As Friend of Supermodel

Frederique van der Wal

As Friend of Supermodel

Marian Seldes

As Datloff Party Guest

David Margulies

As Counselor Adelman

Jeff Mazzola

As Assistant Director

Dick Mingalone

As Camera Operator

Vladimir Bibic

As Director of Photography

Francisco Quijada

As Erno Delucca

Aleksa Palladino

As Production Assistant

Dan Moran

As Jackhammer Operator

Peter Castellotti

As Sound Recordist

A. Lee Morris

As Second Assistant Cameraperson

Maurice Sonnenberg

As Dalton Freed

Craig Ulmschneider

As Production Assistant Daniel

Mina Bern

As Elderly Homeowner

Janet Marlow

As Singing Nun

Tommie Baxter

As Second Nun

Kathleen Doyle

As Father Gladden's Fan

Arthur Berwick

As Father Gladden's Fan

Jodi Long

As Father Gladden's Fan

John Carter

As Father Gladden

Marylouise Burke

As Father Gladden's Fan on Porch

Peter Boyden

As Father Gladden's Fan on Porch

Peter McRobbie

As Father Gladden's Fan on Porch

Maureen McNamara

As Father Gladden's Fan on Porch

Mary Catherine Wright

As Pious Diner

Melinda Eng

As Fashion Designer

Alma Cuervo

As Bruce Bishop's Admirer

Ève Salvail

As Bruce Bishop's Admirer

Polly Adams

As Exercise Tape Fan

Brian McConnachie

As Exercise Tape Fan

Anthony Mason

As Himself

Daisy Prince

As Waiting Room Nurse

Tina Sloan

As Waiting Room Patient

Dayle Haddon

As Waiting Room Patient

Bill Gerber

As Waiting Room Patient

Julie Halston

As Patient With Jowls

Reuben Jackson

As Cameraman at Lupus Office

Skip Rose

As Couple on Beach

Alicia Meer

As Couple on Beach

Becky Ann Baker

As Glenwood High Alumna - Doris

Michael Kell

As Glenwood High Alumna - Nat

Steve Mellor

As Glenwood High Alumna - Eddie

Gerry Becker

As Glenwood High Alumna - Jay Tepper

Ileen Getz

As Glenwood High Alumna - Reunion Announcer

Robert Cuccioli

As Glenwood High Alumna - Monroe Gordon

Surinder Khosla

As V.J. Rajnipal

Frederick Rolf

As Book Reviewer

Ramsey Faragallah

As TV Program Director

William Addy

As Klansman

Patrick Thomas McCarthy

As Klansman

Bernard Addison

As Minister Polynice

Mary Samuels

As TV Production Assistant

Sarah Buff

As TV Production Assistant

Heather Marni

As Teenage Obese Acrobat

Bruno Gunn

As Skinhead

Sean Daloise

As Skinhead

Matthew Sweeney

As Skinhead

Kyle Kulish

As Overweight Achiever

Sam Gray

As Tony's Father

Marilyn Raphael

As Tony's Mother

Antonette Schwartzberg

As Tony's Grandma

Gabriel Millman

As Ricky

Adam Sietz

As Vince

Michael Crecco

As Hotel Clerk

Neal Arluck

As Hotel Clerk

Timothy Jerome

As Hotel Clerk

Joseph Tudisco

As Hotel Clerk

Jim Moody

As Security Guard

Robert Torres

As Security Guard

John Costelloe

As Cop at Hotel

Mary Jo Buttafuoco

As Herself

Joey Buttafuoco

As Himself

Lorri Bagley

As Chekhov-style Writer

Richard Mawe

As Elaine's Book Party Guest

Ted Neustadt

As Elaine's Book Party Guest

Bruce Jay Friedman

As Elaine's Book Party Guest

Erica Jong

As Elaine's Book Party Guest

Clebert Ford

As Elaine's Book Party Guest

Ralph Pope

As Comic's Agent

Rick Mowat

As Comic

Victor Colicchio

As Moving Man in Loft

Robert Cividanes

As Moving Man in Loft

Donegal Fitzgerald

As Moving Man on Street

Howard Erskine

As Senator Paley

Ray Cohen

As Pianist at Wedding

Angel Caban

As Limo Driver

Ingrid Rogers

As Off-Off Broadway Actress

Brian McCormack

As Phil

Gigi Williams

As Fan of Robin Simon

Laura Nativo

As Jailbait (uncredited)