Reese Witherspoon
Lisa Jorgenson
Paul Rudd
George Madison
Owen Wilson
Matty Reynolds
Jack Nicholson
Charles Madison
Kathryn Hahn
Annie
Molly Price
Coach Sally
Shelley Conn
Terry
Tony Shalhoub
Psychiatrist
Mark Linn-Baker
Ron
Lenny Venito
Al
Ron McLarty
George's Lawyer
Domenick Lombardozzi
Bullpen Pitcher
John Tormey
Doorman
Teyonah Parris
Riva
Dean Norris
Softball Coach
Tara Subkoff
Subpoena Woman
Kimberly Spak
Baseball Fan (uncredited)
David A. Gregory
Matty's Teammate (as David Gregory)
Donna Dundon
Annie's Mom
Cyrus Newitt
Annie's Dad
Will Blagrove
Matty's Teammate
Andrew Wilson
Matty's Teammate
Yuki Matsuzaki
Tori
Bill McKinney
Maitre d'
Jim Bouton
Bullpen Coach