Meg Ryan

Kathleen Kelly

Tom Hanks

Joe Fox

Greg Kinnear

Frank Navasky

Parker Posey

Patricia Eden

Heather Burns

Christina Plutzker

Dave Chappelle

Kevin Jackson

Jean Stapleton

Birdie Conrad

Steve Zahn

George Pappas

Dabney Coleman

Nelson Fox

John Randolph

Schulyer Fox

Hallee Hirsh

Annabelle Fox

Jeffrey Scaperrotta

Matt Fox

Cara Seymour

Gillian Quinn

Katie Finneran

Maureen, the Nanny

Michael Badalucco

Charlie

Deborah Rush

Veronica Cash

Veanne Cox

Miranda Margulies

Bruce Jay Friedman

Vince Mancini

Sara Ramirez

Rose, Zabars Cashier

Howard Spiegel

Henry, Zabars Shopper

Diane Sokolow

Zabars Shopper

Julie Kass

Zabars Shopper

Reiko Aylesworth

Thanksgiving Guest

Katie Sagona

Young Kathleen Kelly

Kathryn Meisle

Cecilia Kelly

Nina Zoie Lam

T.V. Reporter

Maggie Murphy

Theater Patron

Michelle Blakely

Shopper

Meredith White

Shopper

Dianne Dreyer

Shopper

Julie Galdieri

Shopper

Leila Nichols

Shopper

Mary A. Kelly

Fox Books Shopper

Chris Messina

Fox Salesperson

Ronobir Lahiri

Man at Cafe Lalo

André Sogliuzzo

Waiter at Lalo

Peter A. Mian

Capeman

Richard Cohen

Starbucks Customer

Enzo Angileri

Starbucks Customer

Nick Brown

Juggler

Ann Fleuchaus

Sarah Mancini

Neil Bonin

Party Guest

Bill McHugh

Party Guest

Santiago Quinones

Decorator

Lynn Grossman

Yvette Fox

Dolores Sirianni

Mother of Twins

Nicole Bernadette

Florist

Jane Adams

Sydney Anne (uncredited)

Cecelia Antoinette

Restaurant Patron (uncredited)

Elwood Edwards

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

Alfonso Gomez-Rejon

Party Guest (uncredited)

Gideon Jacobs

Young Joe Fox (uncredited)

Brick Mason

Man Letting Joe Fox in (uncredited)

Scott Mullin

Male Runner (uncredited)

Logan Steinhardt

Kid in Bookstore (uncredited)

Anthony Welch

Business Executive (uncredited)