- Greg Mottola
- Director
- Jeff Mazzola
- Assistant Director
- Dick Mingalone
- Camera Operator
- Vladimir Bibic
- Director of Photography
- Melanie Griffith
- Nicole Oliver
- Francisco Quijada
- Erno Delucca
- Aleksa Palladino
- Production Assistant
- Dan Moran
- Jackhammer Operator
- Peter Castellotti
- Sound Recordist
- A. Lee Morris
- Second Assistant Cameraperson
- Douglas McGrath
- Bill Gaines
- Kenneth Branagh
- Lee Simon
- Maurice Sonnenberg
- Dalton Freed
- Winona Ryder
- Nola
- Craig Ulmschneider
- Daniel - Production Assistant
- Mina Bern
- Elderly Homeowner
- Janet Marlow
- Singing Nun
- Tommie Baxter
- Second Nun
- Kathleen Doyle
- Father Gladden's Fan
- Arthur Berwick
- Father Gladden's Fan
- Jodi Long
- Father Gladden's Fan
- John Carter
- Father Gladden
- Judy Davis
- Robin Simon
- Monique Fowler
- Jan - Robin's Friend
- Marylouise Burke
- Father Gladden's Fan on Porch
- Peter Boyden
- Father Gladden's Fan on Porch
- Peter McRobbie
- Father Gladden's Fan on Porch
- Maureen McNamara
- Father Gladden's Fan on Porch
- Mary Catherine Wright
- Pious Diner
- J.K. Simmons
- Souvenir Hawker
- Dylan Baker
- Priest at Catholic Retreat
- Charlize Theron
- Supermodel
- Melinda Eng
- Fashion Designer
- Isaac Mizrahi
- Bruce Bishop
- Alma Cuervo
- Bruce Bishop's Admirer
- Eve Salvail
- Bruce Bishop's Admirer
- Polly Adams
- Exercise Tape Fan
- Brian McConnachie
- Exercise Tape Fan
- Irina Pantaeva
- Friend of Supermodel
- Mark Vanderloo
- Friend of Supermodel
- Frederique Van Der Wal
- Friend of Supermodel
- Michael Moon Band
- El Flamingo Band
- Anthony Mason
- Anthony Mason
- Daisy Prince
- Waiting Room Nurse
- Tina Sloan
- Waiting Room Patient
- Dayle Haddon
- Waiting Room Patient
- Bill Gerber
- Waiting Room Patient
- Michael Lerner
- Dr. Lupus
- Julie Halston
- Patient with Jowls
- Renée Lippin
- Second Examining Room Patient
- Kate Burton
- Robin's Friend Cheryl
- Reuben Jackson
- Cameraman at Lupus Office
- Debra Messing
- TV Reporter at Lupus Office
- Carmen Dell'Orefice
- Pinky Virdon
- Joe Mantegna
- Tony Gardella
- Andre Gregory
- John Papadakis
- Famke Janssen
- Bonnie
- Skip Rose
- Couple on Beach
- Alicia Meer
- Couple on Beach
- Becky Ann Baker
- Doris - Glenwood High Alumna
- Michael Kell
- Nat - Glenwood High Alumnus
- Steve Mellor
- Eddie - Glenwood High Alumnus
- Gerry Becker
- Jay Tepper - Glenwood High Alumnus
- Ileen Getz
- Reunion Announcer - Glenwood High Alumna
- Robert Cuccioli
- Monroe Gordon - Glenwood High Alumnus
- Larry Pine
- Philip Datloff
- Surinder Khosla
- V.J. Rajnipal
- Marian Seldes
- Datloff Party Guest
- Frederick Rolf
- Book Reviewer
- David Margulies
- Counselor Adelman
- Ramsey Faragallah
- TV Program Director
- William Addy
- Klansman
- Patrick Thomas McCarthy
- Klansman
- Bernard Addison
- Minister Polynice
- Mary Samuels
- TV Production Assistant
- Sarah Buff
- TV Production Assistant
- Heather Marni
- Teenage Obese Acrobat
- Bruno Gunn
- Skinhead
- Sean Daloise
- Skinhead
- Matthew Sweeney
- Skinhead
- Kyle Kulish
- Overweight Achiever
- Tony Sirico
- Lou DeMarco
- Kenneth Edelson
- Rabbi Kaufman
- Bebe Neuwirth
- Nina - the Hooker
- Sam Gray
- Tony's Father
- Marilyn Raphael
- Tony's Mother
- Antonette Schwartzberg
- Tony's Grandma
- Patti D'Arbanville
- Iris
- Frank Pellegrino
- Frankie
- Gabriel Millman
- Ricky
- Adam Sietz
- Vince
- Gretchen Mol
- Vicky
- Leonardo DiCaprio
- Brandon Darrow
- Michael Crecco
- Hotel Clerk
- Neal Arluck
- Hotel Clerk
- Timothy Jerome
- Hotel Clerk
- Joseph Tudisco
- Hotel Clerk
- Jim Moody
- Security Guard
- Robert Torres
- Security Guard
- Steven Randazzo
- Cop at Hotel
- John Costelloe
- Cop at Hotel
- Mary Jo Buttafuoco
- Self
- Joey Buttafuoco
- Self
- Adrian Grenier
- Darrow Entourage
- Sam Rockwell
- Darrow Entourage
- John Doumanian
- Darrow Entourage
- Lorri Bagley
- Gina - Chekhov-style Writer
- Richard Mawe
- Elaine's Book Party Guest
- Ted Neustadt
- Elaine's Book Party Guest
- Bruce Jay Friedman
- Elaine's Book Party Guest
- Erica Jong
- Elaine's Book Party Guest
- Ned Eisenberg
- Elaine's Book Party Guest
- Clebert Ford
- Elaine's Book Party Guest
- Hank Azaria
- David
- Ralph Pope
- Comic's Agent
- Rick Mowat
- Comic
- Tony Darrow
- Moving Man in Loft
- Victor Colicchio
- Moving Man in Loft
- Robert Cividanes
- Moving Man in Loft
- Donegal Fitzgerald
- Moving Man on Street
- Leslie Shenkel
- Manhattan Moods Assistant Director
- Donna Hanover
- Manhattan Moods Anchor Woman
- Allison Janney
- Evelyn Isaacs
- Howard Erskine
- Senator Paley
- Celia Weston
- Dee Bartholomew
- Donald Trump
- Donald Trump
- Wood Harris
- Al Swayze
- Ray Cohen
- Pianist at Wedding
- Angel Caban
- Limo Driver
- Aida Turturro
- Olga - Psychic
- Ingrid Rogers
- Off-Off Broadway Actress
- Jeffrey Wright
- Greg - Off-Off Broadway Director
- Karen Duffy
- TV Reporter at Premiere
- Brian McCormack
- Phil
- Gigi Williams
- Fan of Robin Simon
- Michael Moon
- Vocals / Guitar - El Flamingo Band
- Peter Dark
- Guitar / Vocals - El Flamingo Band
- Murphy Occhino
- Drums / Vocals - El Flamingo Band
- Randy Jordan
- Bass / Vocals - El Flamingo Band
- Richard Iacona
- Piano - High School Reunion Band
- Tom Kirchner
- Bass - High School Reunion Band
- Stan Persky
- Sax - High School Reunion Band
- Tony Tedesco
- Drums - High School Reunion Band
- Mike Ponella
- Trumpet - High School Reunion Band
- Ron Affif
- Guitar - High School Reunion Band
- Heidi Albertsen
- Heidi Albertsen ( In a scene with Charlize Theron and Kenneth Branagh .
- Casper Andreas
- Nicole's Stylist
- Ethan Aronoff
- Boxing Fan
- Dar Billingham
- Wardrobe Lady
- David Blaine
- Spectator
- Frank Bonsangue
- Movie Patron
- Lauren Burns
- Elaine's Guest
- New York Joe Catalfumo
- Steven DiDio
- Bill Chemerka
- Class Reunion Guest
- Jay Alan Christianson
- Man with Cell Phone
- Tracy Coogan
- Model
- Gary Cowling
- Nicole's Handler
- Michelle Crowe-Paz
- NYC Businesswoman
- Amy de Lucia
- Director's Girlfriend
- Teresa DePriest
- Model
- Sian DeVega
- Fashion Model
- Jill Ragee Downing
- Snob
- Patrick Coleman Duncan
- Audience member
- Lela Edgar
- Model
- Robert Steinman Elden
- Office Manager
- Ken Elston
- Friend at Opening
- Alex Emanuel
- Elaine's Book Party Guest
- Anthony Gestone
- Street Kid #2
- Irene Glezos
- Soho Art Buyer
- Lionel Guy-Bremond
- Extra
- Robert Harriell
- Elaine's Book Party Guest
- Kali Hawk
- Popcorn Girl
- Sonita Henry
- Film Festival Guest
- Markanthony Izzo
- Fan
- Wendy Johnson
- Model
- Vivian Kalinov
- NYC Tourist
- Ralph Kinnard
- Model
- Kristi Kirk
- Model
- Janine Laino
- Upscale Hotel Guest
- Carl Landi
- Dolly Grip
- Nicole Levy
- Lenore Upshaw
- Frank Licari
- Camera Man
- Autumn Lucas
- Waitress
- Ana-Sofia Mastroianna
- DS Worker
- Trish McGettrick
- Script Girl
- Denis McKeown
- Jean Georges Guest
- Josh Mowery
- Wardrobe man
- Laura Nativo
- Jailbait
- George Nicolaidis
- Reunion Guest
- Jina Oh
- Buyer at Fashion Show
- Angela Palmer-Haibach
- Dancer in Club
- Cory Poccia
- Street Kid #1
- Myron Primes
- Party Guest
- Rio Puertollano
- Tourist
- Evan Reynolds
- Fashion Designer
- Joe Richards
- Bradson Grey
- James Rosin
- Casino Gambler
- Yolonda Ross
- (uncredited) (unconfirmed)
- Michelle Rouhani
- Groom Family Member
- Chrystèle Saint Louis Augustin
- Nicole's Assistant
- April Sandmeyer
- Film Premiere Guest
- Kevin Scullin
- Stanhope Doorman
- Ian Somerhalder
- (uncredited) (unconfirmed)
- Greg Sullivan
- Filmgoer
- Carlos Valencia
- Model
- Sanny van Heteren
- Celebrity at The Zigfield Theatre
- Valeria Von Leczycki Goncharova Barrett
- Aristocratic Lady / Celebrity (uncredited)
- Roshumba Williams
- Bruce Bishop Admirer
- Gaël Zaks
- The Young Actor
- Diana C. Zollicoffer
- Newscaster
