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 Himself

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)