| 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 | ESPN Sportscaster |
| Zack Shada | Mad Dawg Killa |
| Jason Abustan | Clubgoer |
| Gina Aponte | Tour Bus Tourist |
| Brad Ausmus | Self |
| James Azrael | Gutterballs Bowler |
| Holly Barrett | Patron |
| Darlene Benigno | Cubs Fan |
| Alan Bovinett | Clubgoer |
| Arden Cho | VIP Party Guest |
| Katie Cleary | Girlfriend |
| Lauren Cokeley | Concert Goer |
| Michael Cook | Art Fair Patron |
| Tiffany Cooksey | Club Goer |
| Julia Copeland | Club Goer / Concert Attendant / Art Fair Patron |
| Justin Dabney | Bowler / Dancer |
| Kelley Daugherty | Concert Goer |
| Rachel Daugherty | Cub fan |
| Rebecca Michelle David | Cubs Fan |
| Sue Durso | Wrigley Field, Bowling, Street Scenes |
| Matt Dworzanczyk | Art Fair Attendant |
| Mark Falvo | Cubs Fan |
| Nick Ferrin | Concert Goer |
| Reese Foster | Hero at the Bar |
| Jason Frederick | Bus Patron |
| John Gearries | Concert Goer |
| Laurie Faith Gibson | Dancer |
| Marisol Giraud | Cubs Fan |
| George Glynn | Casey |
| Jennifer A. Goodman | Cubs Fan |
| John R. Haley | Man in Ballroom |
| Todd Hollandsworth | Self |
| Anna Ingenthron | Cubs Fan |
| Andrew Irvin | Clubgoer |
| Carlyn Janus | Pedestrian |
| Ian Kalanges | Man in Concert Scene |
| James Kim | Morgan |
| Robert Kramer | Pedestrian |
| Kristen Kruchowski | Becca |
| Tim Krueger | Cubs Fan |
| Jay Lavender | Cubs fan sitting next to Jon Favreau |
| Aly Law | Featured Dancer |
| Joseph Lazicki | Pedestrian |
| Nathan Lee | Club Goer |
| Alexandra LoRusso | Balcony Dancer at Concert |
| Jamie Louachai | Dancer / Art Fair Patron |
| Erin Luboff | Art Fair Patron |
| Jon Marshall | Background |
| Theo Marshall | Date |
| Mercedes Mason | Goblet Girl |
| Doug Mercado | Bar Patron |
| Frank Mercuri | Man walking on the street during end credits |
| Chad Meyer | Restaurant Patron |
| Lori Miller | Cubs Fan |
| Brad Nelson | Greg |
| William Nero Jr. | Kid Playing at Park |
| Kelly Nienaltowski | Girl in Bowling Alley / Art Fair Patron |
| Rebecca Norris | Pedestrian |
| Katherine M. O'Connor | Girl in Bowling Alley / Cubs Fan / Concert Goer / Art Fair Patron |
| Chris Papadopoulos | Club Patron |
| Jamie Julia Parker | Notre Dame Fan / Art Fair Patron |
| Libby Pedersen | Woman at the Club |
| Andrew Perta | Boat Tourist |
| Kevin Pitcairn | Cubs Fan in Hawaiian Shirt |
| Marc Radz | Cubs Fan |
| Benjamin Riley | Bartender |
| Jonathan Samuels | Nightclub Patron |
| Jesse Santoyo | Pedestrian |
| Luke James Schneider | Art Fair Patron |
| Gary Sedlock | Tourist on Bus |
| Michael Stailey | Clubgoer |
| January Stern | Artist Exhibitor |
| Rahul Thakkar | Tourist |
| Marko Tomic | Concert Goer |
| Giota Trakas | Shopper |
| Ron Valdez | Art Fair Patron |
| Tim Vance | Cubs Fan |
| Brigitte Wulf | 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 United States
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