2006 · 1h 46m · PG-13
…pick a side.
A couple's break-up proceeds to get uglier and nastier by the moment as each tries to keep their luxurious condo from the other.
In Chicago, the art dealer Brooke Meyers feels not appreciated and neglected by her immature boyfriend Gary Grobowski, who is partner with his two brothers in a tourism business, and decides to break-up with him to make Gary miss her. Gary misunderstands her true intention, both follow the wrong advice of family members and friends, beginning a war of sexes with no winner.
Jennifer Aniston
Brooke Meyers
Vince Vaughn
Gary Grobowski
Joey Lauren Adams
Addie
Ann-Margret
Wendy Meyers
Jason Bateman
Riggleman
Judy Davis
Marilyn Dean
Vincent D'Onofrio
Dennis Grobowski
Jon Favreau
Johnny O
Cole Hauser
Lupus Grobowski
John Michael Higgins
Richard Meyers
Justin Long
Christopher
Ivan Sergei
Carson Wigham
Keir O'Donnell
Date (Paul)
Geoff Stults
Date (Mike)
Vernon Vaughn
Howard Meyers
Elaine Robinson
Carol Grobowski
Jane Alderman
Mrs. Grobowski
Jacqueline Williams
Shondra
Peter Billingsley
Andrew
Jane Hu
Diane
Rebecca Spence
Jen
Mary-Pat Green
Mischa
Jessica Vilchis
Hot Girl
Samantha Albert
Debbie
Susan Messing
Tourist
William Dick
Waiter
Jenna Hurt
Poker Girl
Jessica Stramer
Poker Girl
Ashley Giancola
Poker Girl
Lanae Sahs
Poker Girl
Sharon Vaughn
Boat Tourist
Nydia Rodriguez Terracina
Boat Tourist
Phil Ridarelli
Boat Tourist
Rhett Miller
Old 97's
Murry Hammond
Old 97's
Ken Bethea
Old 97's
Philip Peeples
Old 97's
Eric Bradley
Tone Ranger
Eduardo N. Martinez
Hot Dog Vendor
Chuck Stubbings
Country Clubber
Linda Cohn
ESPN Sportscaster (voice)
Arden Cho
VIP Party Guest (uncredited)
Mercedes Mason
Goblet Girl (uncredited)
Jennifer A. Goodman
Cubs Fan (uncredited)