Drew Barrymore as Skylar Dandridge

Edward Norton as Holden Spence

Alan Alda as Bob Dandridge

Julia Roberts as Von Sidell

Woody Allen as Joe Berlin

Lukas Haas as Scott Dandridge

Goldie Hawn as Steffi Dandridge

Gaby Hoffmann as Lane Dandridge

Natalie Portman as Laura Dandridge

Tim Roth as Charles Ferry

David Ogden Stiers as Holden's Parent

Natasha Lyonne as Djuna 'D.J.' Berlin

Billy Crudup as Ken

Robert Knepper as Greg

Diva Gray as Nanny

Patrick Cranshaw as Grandpa

Kevin Hagan as Doorman

Itzhak Perlman as Self

Trude Klein as Frieda

Isiah Whitlock, Jr. as Cop

Edward Hibbert as Harry Winston Salesman

Colleen Dunn as Harry Winston Dancer

Susan Misner as Harry Winston Dancer

Frederick Rolf as Le Cirque Waiter

Timothy Jerome as X-Ray Room Doctor

Daisy Prince as Nurse

Ruth Gottschall as Hospital Dancer

Monica McSwain as Hospital Dancer

Jill Nicklaus as Hospital Dancer

Myra Lucretia Taylor as Hospital Dancer

Paolo Seganti as DJ's Venice Date

Robert Khakh as Cab Driver

Scotty Bloch as Holden's Parent

Valda Setterfield as Ghost Dancer

Tony Sirico as Escaped Convict

Ray Garvey as Escaped Convict

Christy Carlson Romano as Trick-or-Treat Child

Gabriel Millman as Trick-or-Treat Child

Ed Hodson as Scott's Doctor

Darren Lee as Groucho Party Dancer

Cynthia Onrubia as Groucho Party Dancer

Nancy Ticotin as Groucho Party Dancer

Emily Bindiger as Helen Miles Singer

Michael Mark as Helen Miles Singer

Ami Almendral as Nanny

Madeline Balmaceda as Nanny

Vivian Cherry as Nurse

Tommie Baxter as Old Woman

Jeff DeRocker as Homeless Man

Cherylyn Jones as Mannequin

Tina Paul as Mannequin / Harry Winston Dancer

Vikki Schnurr as Mannequin

Navah Perlman as Pianist

Barbara Hollander as Claire

John Griffin as Jeffrey Vandermost

Waltrudis Buck as Psychiatrist

Kevin Bogue as Harry Winston Dancer

Pamela Everett as Harry Winston Dancer

Gregory Mitchell as Harry Winston Dancer

Dana Moore as Harry Winston Dancer

Troy Myers as Harry Winston Dancer

Joe Orrach as Harry Winston Dancer

Michael O'Steen as Harry Winston Dancer

Luis Martin Perez as Harry Winston Dancer / Hospital Dancer / Ghost Dancer / Groucho Party Dancer

Krissy Richmond as Harry Winston Dancer

Linda Kuriloff as Nurse

Helen Miles as Nurse / The Helen Miles Singers

Arlene Martin as Nurse / The Helen Miles Singers

Rene Ceballos as Hospital Dancer

Colton Green as Hospital Dancer

Lisa LeGuillou as Hospital Dancer

Joe Locarro as Hospital Dancer

Andrew Pacho as Hospital Dancer

John Selya as Hospital Dancer

Jo Telford as Hospital Dancer

Andrea Piedimonte Bodini as Alberto

Gerry Burkhardt as Ghost Dancer

Eileen Casey as Ghost Dancer

Shelley Frankel as Ghost Dancer

Fred Mann III as Ghost Dancer

Kathy Sanson as Ghost Dancer

Frank Pietri as Ghost Dancer

Robert Walker as Rapper

Devalle Hayes as Rapper

Damon McCloud as Rapper

Tommy John as Trick-or-Treat Child

Lindsy Canuel as Trick-or-Treat Child

Richard Cummings as Trick-or-Treat Child

Kristen Pettet as Trick-or-Treat Child

Patrick Lavery as Trick-or-Treat Child

Jonathan Giordano as Trick-or-Treat Child

Michel Moinot as Bob's Doctor

Don Correia as Groucho Party Dancer

Sean Grant as Groucho Party Dancer

Roland Hayes as Groucho Party Dancer

Delphine T. Mantz as Groucho Party Dancer

Joanne McHugh as Groucho Party Dancer

John Mineo as Groucho Party Dancer

Willie Rosario as Groucho Party Dancer

Jerome Vivona as Groucho Party Dancer

Cindy Cobitt as Helen Miles Singer

Al Dana as Helen Miles Singer

Kevin De Simone as Helen Miles Singer

Paul Evans as Helen Miles Singer

Chrissy Faith as Helen Miles Singer

Jeff Lyons as Helen Miles Singer

Jenna Miles as Helen Miles Singer

Robert Ragaini as Helen Miles Singer

Lenny Roberts as Helen Miles Singer

Annette Sanders as Helen Miles Singer

Terry Textor as Helen Miles Singer

Vanéese Y. Thomas as Helen Miles Singer

Ashley H. Wilkinson as Helen Miles Singer

Chris Cardona as Italy Dinner Guest (uncredited)

Olivia Hayman as Skylar (singing voice) (uncredited)

Lisa Cangelosi as Cigar Girl (uncredited)

Malinda Farrington as Harry Winston Dancer (uncredited)