Reese Witherspoon as Lisa Jorgenson

Paul Rudd as George

Owen Wilson as Manny

Jack Nicholson as Charles

Kathryn Hahn as Annie

Molly Price as Coach Sally

Shelley Conn as Terry

Tony Shalhoub as Psychiatrist

Mark Linn-Baker as Ron

Lenny Venito as Al

Ron McLarty as George's Lawyer

Domenick Lombardozzi as Bullpen Pitcher

John Tormey as Doorman

Teyonah Parris as Riva

Dean Norris as Softball Coach

Tara Subkoff as Subpoena Woman

Kimberly Spak as Baseball Fan (uncredited)

David A. Gregory as Matty's Teammate (as David Gregory)

Donna Dundon as Annie's Mom

Cyrus Newitt as Annie's Dad

Will Blagrove as Matty's Teammate

Andrew Wilson as Matty's Teammate

Yuki Matsuzaki as Tori

Bill McKinney as Maitre d'

Jim Bouton as Bullpen Coach

Ken Farnell as Bus Driver (as Kenny Farnell)

Mary Gallagher as Other Female Coach

Aileen Zoccola as Player's Wife

Sachi Jonas as Player's Wife

Amanda Moshay as Player's Wife

Lyssa Roberts as Groped Girl (as Lyssa Lee Roberts)

Seth Sanders as Cocky Agent

Elyse Braner as U.S. National Team

Ryann Hendricks as U.S. National Team

Jessi Sheldon as U.S. National Team (as Jessi Moore)

Amanda Freed as U.S. National Team

Jaime Wohlbach as U.S. National Team

Anjelica Selden as U.S. National Team

Lovieanne Jung as U.S. National Team

Suze Kilner as U.S. National Team

Brian Distance as U.S. National Team

Michael Toolan-Roche as U.S. National Team

Caitlin Hanrahan as U.S. National Team

Deanna Vecchio as U.S. National Team

Samantha Yodowitz as U.S. National Team

Crystl Bustos as U.S. National Team

Andrea Duran as U.S. National Team

Jackie Dempsey as U.S. National Team

Tara Henry as U.S. National Team

Carri Martin as U.S. National Team

Greg Pronko as Security Guard #2

Daymien Valentino as Translator

Jeff Ayars as Job Fair Candidate (uncredited)

Nate Bailey as Dr. J. Ford (uncredited)

Scott Barry as Driver (Precision) (uncredited)

Terrence Beasor as Lisa's Dad (uncredited)

Alexandra Begg as Baseball Player's Wife (uncredited)

Jacob Bertrand as Boy (uncredited)

Robert Bizik as Locksmith (uncredited)

Ian Bonner as Lawyer (uncredited)

Charlie Bonnin as Young Lisa's Dad (uncredited)

Anthony Bradford as Partygoer #1 (uncredited)

Rachel Breitag as Gorgeous Girl #1 (uncredited)

Ernest E. Brown as Restaurant Patron (uncredited)

Laura Bryce as Gorgeous Girl SI (uncredited)

Jennifer Butler as Charles' Paralegal (uncredited)

Catherine Cahill as Wealthy Woman (uncredited)

Kimberly Lynn Campbell as U.S. National Team (uncredited)

Maria Cecile Callier as Spectator and Pedestrian (uncredited)

Mustafa Cimen as Foreign Diplomat (uncredited)

Sheri Cohen as Frisbee Player (uncredited)

Chris Conlon as Bullpen Pitcher (uncredited)

Moogega Cooper as College Student (uncredited)

Kirk Curran as College Student (uncredited)

Jessica Czop as Groupie (uncredited)

Tom Delconte as Charles' Lawyer (uncredited)

Patricia DiZebba as Condo Resident (uncredited)

Robin Dorsey as Upscale Shopper (uncredited)

Bennett Dunn as Restaurant Bartender (uncredited)

Cindy Engle as Pedestrian (uncredited)

Amy Gieske as Nationals Fan (uncredited)

Philip Greene as Baseball Fan (uncredited)

Doug Henderson as Tourist (uncredited)

Ken Holliday as Baseball Fan (uncredited)

Sidmar Holloman as Fan (uncredited)

George Kardulias as Baseball Fan in the Bleachers (uncredited)

Jonathan Karp as Busboy (uncredited)

Basil Kershner as Player's Parent (uncredited)

Steven J. Klaszky as Pedestrian (uncredited)

Atif Lanier as U.S. National Team (uncredited)

Traci Law as Lawyer (uncredited)

Alexander Lee as DC Businessman (uncredited)

Koa Lang as Waiter (uncredited)

Chris Luensman as Bar Patron (uncredited)

Quang Ly as Computer Tech (uncredited)

Brian M. Martin as Backpacking Student (uncredited)

Cindy Marie Martin as Nationals Fan (uncredited)

Marguerite Mastromatto as Hospital Nurse (uncredited)

Christian Polk McRee as Softball Player (uncredited)

Patsy Meck as Charles' Maid (uncredited)

John Mitchell as Aussie Baseball Fan (uncredited)

Mike Monroe as Bartender (uncredited)

Paul Monte Jr. as Drunk Teammate (uncredited)

Christian Monturano as Rich Baseball Player (uncredited)

Noah Baron as Baseball Fan (uncredited)