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| Directed by | |
|---|---|
 | Peyton Reed |
| Starring | ||
|---|---|---|
 | Vince Vaughn | Gary Grobowski |
| Jennifer Aniston | Brooke Meyers |
| Joey Lauren Adams | Addie |
| Cole Hauser | Lupus Grobowski |
 | Jon Favreau | Johnny O |
 | Jason Bateman | Riggleman |
| Judy Davis | Marilyn Dean |
| Justin Long | Christopher |
| Ivan Sergei | Carson Wigham |
| John Michael Higgins | Richard Meyers |
| Ann-Margret | Wendy Meyers |
| Vernon Vaughn | Howard Meyers |
| Vincent D'Onofrio | Dennis Grobowski |
| Elaine Robinson | Carol Grobowski |
| Jane Alderman | Mrs. Grobowski |
| Jacqueline Williams | Shondra |
| Peter Billingsley | Andrew |
| Jane Hu | Diane |
| Rebecca Spence | Jen |
| Mary-Pat Green | Mischa |
| Keir O'Donnell | Date |
| Geoff Stults | Mike |
| Tiffany L. Addison | Waitress |
| Jessica Vilchis | Hot Girl |
| Lisa Pace | Hot Girl |
| Samantha Albert | Debbie |
| Susan Messing | Tourist |
| Wayne A. Brown | Tourist |
| Maynard Love | 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 |
| Gunnar Madsen | Tone Ranger |
| Karl Solis | Tone Ranger |
| Michael Winther | Tone Ranger |
| Eric Bradley | Tone Ranger |
| Paul Peterson | Tone Ranger |
| Sean P. Gorecki | Tone Ranger |
| Eduardo N. Martinez | Hot Dog Vendor |
| Chuck Stubbings | Country Clubber |
| Ryan Cowhey | Andrew Jr. |
| Megan Klein | Sally |
| Trisha Vargo | Riv Bartender |
| Julia Neary | Riv Ticket Taker |
| Linda Cohn voice | ESPN Sportscaster |
| Zack Shada voice | Mad Dawg Killa |
| Jason Abustan uncredited | Clubgoer |
| Gina Aponte uncredited | Tour Bus Tourist |
| Brad Ausmus uncredited | Self |
| James Azrael uncredited | Gutterballs Bowler |
| Holly Barrett uncredited | Patron |
| Darlene Benigno uncredited | Cubs Fan |
| Alan Bovinett uncredited | Clubgoer |
| Arden Cho uncredited | VIP Party Guest |
| Katie Cleary uncredited | Girlfriend |
| Lauren Cokeley uncredited | Concert Goer |
| Michael Cook uncredited | Art Fair Patron |
| Tiffany Cooksey uncredited | Club Goer |
| Julia Copeland uncredited | Club Goer / Concert Attendant / Art Fair Patron |
| Justin Dabney uncredited | Bowler / Dancer |
| Kelley Daugherty uncredited | Concert Goer |
| Rachel Daugherty uncredited | Cub fan |
| Rebecca Michelle David uncredited | Cubs Fan |
| Sue Durso uncredited | Wrigley Field, Bowling, Street Scenes |
| Matt Dworzanczyk uncredited | Art Fair Attendant |
| Mark Falvo uncredited | Cubs Fan |
| Nick Ferrin uncredited | Concert Goer |
| Reese Foster uncredited | Hero at the Bar |
| Jason Frederick uncredited | Bus Patron |
| John Gearries uncredited | Concert Goer |
| Laurie Faith Gibson uncredited | Dancer |
| Marisol Giraud uncredited | Cubs Fan |
| George Glynn uncredited | Casey |
| Jennifer A. Goodman uncredited | Cubs Fan |
| John R. Haley uncredited | Man in Ballroom |
| Todd Hollandsworth uncredited | Self |
| Anna Ingenthron uncredited | Cubs Fan |
| Andrew Irvin uncredited | Clubgoer |
| Carlyn Janus uncredited | Pedestrian |
| Ian Kalanges uncredited | Man in Concert Scene |
| James Kim uncredited | Morgan |
| Robert Kramer uncredited | Pedestrian |
| Kristen Kruchowski uncredited | Becca |
| Tim Krueger uncredited | Cubs Fan |
| Jay Lavender uncredited | Cubs fan sitting next to Jon Favreau |
| Aly Law uncredited | Featured Dancer |
| Joseph Lazicki uncredited | Pedestrian |
| Nathan Lee uncredited | Club Goer |
| Alexandra LoRusso uncredited | Balcony Dancer at Concert |
| Jamie Louachai uncredited | Dancer / Art Fair Patron |
| Erin Luboff uncredited | Art Fair Patron |
| Jon Marshall uncredited | Background |
| Theo Marshall uncredited | Date |
| Mercedes Mason uncredited | Goblet Girl |
| Doug Mercado uncredited | Bar Patron |
| Frank Mercuri uncredited | Man walking on the street during end credits |
| Chad Meyer uncredited | Restaurant Patron |
| Lori Miller uncredited | Cubs Fan |
| Brad Nelson uncredited | Greg |
| William Nero Jr. uncredited | Kid Playing at Park |
| Kelly Nienaltowski uncredited | Girl in Bowling Alley / Art Fair Patron |
| Rebecca Norris uncredited | Pedestrian |
| Katherine M. O'Connor uncredited | Girl in Bowling Alley / Cubs Fan / Concert Goer / Art Fair Patron |
| Chris Papadopoulos uncredited | Club Patron |
| Jamie Julia Parker uncredited | Notre Dame Fan / Art Fair Patron |
| Libby Pedersen uncredited | Woman at the Club |
| Andrew Perta uncredited | Boat Tourist |
| Kevin Pitcairn uncredited | Cubs Fan in Hawaiian Shirt |
| Marc Radz uncredited | Cubs Fan |
| Benjamin Riley uncredited | Bartender |
| Jonathan Samuels uncredited | Nightclub Patron |
| Jesse Santoyo uncredited | Pedestrian |
| Luke James Schneider uncredited | Art Fair Patron |
| Gary Sedlock uncredited | Tourist on Bus |
| Michael Stailey uncredited | Clubgoer |
| January Stern uncredited | Artist Exhibitor |
| Rahul Thakkar uncredited | Tourist |
| Marko Tomic uncredited | Concert Goer |
| Giota Trakas uncredited | Shopper |
| Ron Valdez uncredited | Art Fair Patron |
| Tim Vance uncredited | Cubs Fan |
| Brigitte Wulf uncredited | Cubs Fan |
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Puerto Rico release date: 1st June 2006
Canada release date: 2nd June 2006 United States release date: 2nd June 2006
Australia release date: 8th June 2006
Netherlands release date: 15th June 2006
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