Edward Norton ... Holden
Drew Barrymore ... Skylar
Diva Gray ... Nanny
Ami Almendral ... Nanny
Madeline Balmaceda ... Nanny
Vivian Cherry ... Nurse
Tommie Baxter ... Old Woman
Jeff DeRocker ... Homeless Man (as Jeff Derocker)
Cherylyn Jones ... Mannequin
Tina Paul ... Mannequin / Harry Winston Dancer
Vikki Schnurr ... Mannequin
Natasha Lyonne ... DJ
Kevin Hagan ... Doorman
Alan Alda ... Bob
Gaby Hoffmann ... Lane
Natalie Portman ... Laura
Lukas Haas ... Scott
Trude Klein ... Frieda
Goldie Hawn ... Steffi
Itzhak Perlman ... Himself
Navah Perlman ... Pianist
Barbara Hollander ... Claire
John Griffin ... Jeffrey Vandermost
Julia Roberts ... Von
Waltrudis Buck ... Psychiatrist
Patrick Cranshaw ... Grandpa
Isiah Whitlock Jr. ... Cop (as Isiah Whitlock)
Woody Allen ... Joe
Edward Hibbert ... Harry Winston Salesman
Kevin Bogue ... Harry Winston Dancer
Colleen Dunn ... Harry Winston Dancer
Pamela Everett ... Harry Winston Dancer
Susan Misner ... Harry Winston Dancer
Gregory Mitchell ... Harry Winston Dancer
Dana Moore ... Harry Winston Dancer
Troy Myers ... Harry Winston Dancer
Joe Orrach ... Harry Winston Dancer
Michael O'Steen ... Harry Winston Dancer
Luis Martin Perez ... Harry Winston Dancer / Hospital Dancer / Ghost Dancer / Groucho Party Dancer
Krissy Richmond ... Harry Winston Dancer
Frederick Rolf ... Le Cirque Waiter
Timothy Jerome ... X-Ray Room Doctor
Daisy Prince ... Nurse
Linda Kuriloff ... Nurse (as Linda Maurel-Sithole)
Helen Miles ... Nurse / The Helen Miles Singers
Arlene Martin ... Nurse / The Helen Miles Singers (as Arlene Martell)
Rene Ceballos ... Hospital Dancer (as René Ceballos)
Ruth Gottschall ... Hospital Dancer
Colton Green ... Hospital Dancer
Lisa LeGuillou ... Hospital Dancer (as Lisa Leguillou)
Joe Locarro ... Hospital Dancer
Monica McSwain ... Hospital Dancer
Jill Nicklaus ... Hospital Dancer
Andrew Pacho ... Hospital Dancer
John Selya ... Hospital Dancer
Myra Lucretia Taylor ... Hospital Dancer
Jo Telford ... Hospital Dancer
Paolo Seganti ... DJ's Venice Date
Andrea Piedimonte ... Alberto
Robert Knepper ... Greg
Billy Crudup ... Ken
Robert Khakh ... Cab Driver
Tim Roth ... Charles Ferry
Scotty Bloch ... Holden's Parent
David Ogden Stiers ... Holden's Parent
Gerry Burkhardt ... Ghost Dancer
Eileen Casey ... Ghost Dancer
Shelley Frankel ... Ghost Dancer
Fred Mann III ... Ghost Dancer (as Fred C. Mann III)
Kathy Sanson ... Ghost Dancer
Valda Setterfield ... Ghost Dancer
Frank Pietri ... Ghost Dancer
Robert Walker ... Rapper
Devalle Hayes ... Rapper
Damon McCloud ... Rapper
Tony Sirico ... Escaped Convict
Ray Garvey ... Escaped Convict
Tommy John ... Trick-or-Treat Child
Lindsy Canuel ... Trick-or-Treat Child
Richard Cummings ... Trick-or-Treat Child
Kristen Pettet ... Trick-or-Treat Child
Patrick Lavery ... Trick-or-Treat Child
Christy Romano ... Trick-or-Treat Child
Jonathan Giordano ... Trick-or-Treat Child
Gabriel Millman ... Trick-or-Treat Child
Ed Hodson ... Scott's Doctor
Michel Moinot ... Bob's Doctor
Don Correia ... Groucho Party Dancer
Sean Grant ... Groucho Party Dancer
Roland Hayes ... Groucho Party Dancer
Darren Lee ... Groucho Party Dancer
Delphine T. Mantz ... Groucho Party Dancer
Joanne McHugh ... Groucho Party Dancer
John Mineo ... Groucho Party Dancer
Cynthia Onrubia ... Groucho Party Dancer
Willie Rosario ... Groucho Party Dancer
Jerome Vivona ... Groucho Party Dancer
Nancy Ticotin ... Groucho Party Dancer
Emily Bindiger ... Helen Miles Singer
Cindy Cobitt ... Helen Miles Singer
Al Dana ... Helen Miles Singer
Kevin De Simone ... Helen Miles Singer (as Kevin DeSimone)
Paul Evans ... Helen Miles Singer
Chrissy Faith ... Helen Miles Singer
Jeff Lyons ... Helen Miles Singer
Michael Mark ... Helen Miles Singer
Jenna Miles ... Helen Miles Singer
Robert Ragaini ... Helen Miles Singer
Lenny Roberts ... Helen Miles Singer
Annette Sanders ... Helen Miles Singer
Terry Textor ... Helen Miles Singer
Vanéese Y. Thomas ... Helen Miles Singer (as Vaneese Thomas)
Ashley H. Wilkinson ... Helen Miles Singer
Lisa Cangelosi ... Cigar Girl (uncredited)
Chris Cardona ... Italy Dinner Guest (uncredited)
Olivia Hayman ... Skylar (singing voice) (uncredited)

Holden and Skylar are in love with each other. Skylar lives with a large and extended family on Manhattan. Her parents, Bob and Steffi have been married to each other for many years. Joe, a friend of theirs, who has a daughter, DJ, with Steffi. After yet another relationship, Joe is alone again. He flees to Venice, and meets Von, and makes her believe that he is the man of her dreams. However, their happiness is fake all the way, and she returns to her previous husband. Steffi spends her time with charity work, and manages to break up Skylars and Holdens relation when she introduces Skylar to a released jailbird, Charles Ferry.

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