Meg Ryan

Character: Kathleen Kelly

Tom Hanks

Character: Joe Fox

Greg Kinnear

Character: Frank Navasky

Parker Posey

Character: Patricia Eden

Heather Burns

Character: Christina Plutzker

Dave Chappelle

Character: Kevin Jackson

Jean Stapleton

Character: Birdie Conrad

Steve Zahn

Character: George Pappas

Dabney Coleman

Character: Nelson Fox

John Randolph

Character: Schulyer Fox

Hallee Hirsh

Character: Annabelle Fox

Jeffrey Scaperrotta

Character: Matt Fox

Cara Seymour

Character: Gillian Quinn

Katie Finneran

Character: Maureen, the Nanny

Michael Badalucco

Character: Charlie

Deborah Rush

Character: Veronica Cash

Veanne Cox

Character: Miranda Margulies

Bruce Jay Friedman

Character: Vince Mancini

Sara Ramirez

Character: Rose, Zabars Cashier

Howard Spiegel

Character: Henry, Zabars Shopper

Diane Sokolow

Character: Zabars Shopper

Julie Kass

Character: Zabars Shopper

Reiko Aylesworth

Character: Thanksgiving Guest

Katie Sagona

Character: Young Kathleen Kelly

Kathryn Meisle

Character: Cecilia Kelly

Nina Zoie Lam

Character: T.V. Reporter

Maggie Murphy

Character: Theater Patron

Michelle Blakely

Character: Shopper

Meredith White

Character: Shopper

Dianne Dreyer

Character: Shopper

Julie Galdieri

Character: Shopper

Leila Nichols

Character: Shopper

Mary A. Kelly

Character: Fox Books Shopper

Chris Messina

Character: Fox Salesperson

Ronobir Lahiri

Character: Man at Cafe Lalo

André Sogliuzzo

Character: Waiter at Lalo

Peter A. Mian

Character: Capeman

Richard Cohen

Character: Starbucks Customer

Enzo Angileri

Character: Starbucks Customer

Nick Brown

Character: Juggler

Ann Fleuchaus

Character: Sarah Mancini

Neil Bonin

Character: Party Guest

Bill McHugh

Character: Party Guest

Santiago Quinones

Character: Decorator

Lynn Grossman

Character: Yvette Fox

Dolores Sirianni

Character: Mother of Twins

Nicole Bernadette

Character: Florist

Jane Adams

Character: Sydney Anne (uncredited)

Cecelia Antoinette

Character: Restaurant Patron (uncredited)

Elwood Edwards

Character: Online 'You've Got Mail' Voice (voice) (uncredited)

Alfonso Gomez-Rejon

Character: Party Guest (uncredited)

Gideon Jacobs

Character: Young Joe Fox (uncredited)

Brick Mason

Character: Man Letting Joe Fox in (uncredited)

Scott Mullin

Character: Male Runner (uncredited)

Logan Steinhardt

Character: Kid in Bookstore (uncredited)

Anthony Welch

Character: Business Executive (uncredited)