Dean Norris

Softball Coach

Kathryn Hahn

Annie

Owen Wilson

Matty Reynolds

Tony Shalhoub

Psychiatrist

Lenny Venito

Al

Reese Witherspoon

Lisa Jorgenson

Paul Rudd

George Madison

Teyonah Parris

Riva

Domenick Lombardozzi

Bullpen Pitcher

Jack Nicholson

Charles Madison

Bill McKinney

Maitre d'

James L. Brooks

Director

Richard Sakai

Executive Producer

Ron McLarty

George's Lawyer

Tara Subkoff

Subpoena Woman

John Tormey

Doorman

Andrew Wilson

Matty's Teammate

John D. Schofield

Executive Producer

Yuki Matsuzaki

Tori

Will Blagrove

Matty's Teammate

Molly Price

Coach Sally

Shelley Conn

Terry

Mark Linn-Baker

Ron

Kimberly Spak

Baseball Fan (uncredited)

David A. Gregory

Matty's Teammate

Donna Dundon

Annie's Mom

Cyrus Newitt

Annie's Dad