Richard Gere as Will Keane

Winona Ryder as Charlotte Fielding

Anthony LaPaglia as John Volpe

Elaine Stritch as Dolores "Dolly" Talbot

Vera Farmiga as Lisa Tyler

Sherry Stringfield as Sarah

Jill Hennessy as Lynn

J.K. Simmons as Dr. Tom Grandy

Sam Trammell as Simon

Mary Beth Hurt as Dr. Sibley

Kali Rocha as Shannon

Bill Raymond as Michael (Doorman)

Tawny Cypress as Melissa

Steven Randazzo as Alberto

George Spielvogel III as Netto

Ranjit Chowdhry as Fakir

Toby Poser as Autumn Woman #1

Audrey Quock as Eriko

Gabriel Portuondo as 458 Waiter

Laurent Schwaar as 458 Waiter

Patrick Price as 458 Waiter

Ted Koch as 458 Bartender

Alvin H. Einbender as 458 Bartender

Daniella van Graas as Model at Bar

Rachel Nichols as Model at Bar

Steven Ravid as 458 Customer

Ron Emanuel as 458 Customer

Dan Camins as 458 Customer

John Guidera as 458 Customer

Russell Hunston as 458 Customer

Nik Pjeternikaj as 458 Customer

Paige Handler as Charlotte's Birthday Friend

Liza Lapira as Charlotte's Birthday Friend

Sarah Teresa Burns as Little Girl at Playground

Earl Carroll as Will's Driver

David Filippi as Taxi Driver

Becca Lee as Michelle

Estelle Robinson as Old Frail Lady

Brittney Bunkis as Little Girl at Museum

Delores Mitchell as Librarian

Hatsumi Yoshida as Clown at Halloween Party

Kristi Lee Guinness as 50's Girl at Halloween Party

Luca Waldman as Vampire at Halloween Party

Daniella Canterman as Twin

Deanna Canterman as Twin

Harry Burney as Choirmaster

Cheyne M. Hansen as Boy at Rockerfeller

Iris Flick as Nurse at New Haven Hospital

Pamela Twyble as Nurse at Cleveland Heart Institute

Kathleen Goldpaugh as St. Vincent's Nurse

Robert Plunket as Grubby Man

Shawna Bermender as Ballroom Dancer (uncredited)

Lindsay Canton as Young Teacher at Museum (uncredited)

Jamie Harrold as (uncredited)

Kathryn Hayzer as Ballroom Dancer (uncredited)

Timothy Huang as 458 Waiter (uncredited)

Christopher Lucas as Dance Partner (uncredited)

Nami Paix as Charlotte's Birthday Friend (uncredited)

Rohan Quine as The Moroccan (uncredited)

Adriana Souza as Ballroom Dancer (uncredited)

Randy Troy as Package Boy (uncredited)

Jade Viggiano as Good Fairy Witch (uncredited)