

07/09/1998
The career and personal life of writer Lee are at a standstill, so he divorces his bashful wife, Robin, and dives into a new job as an entertainment journalist. His assignments take him to the swankiest corners of Manhattan, but as he jumps from one lavish party to another and engages in numerous empty romances, he starts to doubt the worth of his work. Meanwhile, top TV producer Tony falls for Robin and introduces her to the world of 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)
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