 | Owen Wilson als Dupree |
 | Kate Hudson als Molly |
 | Matt Dillon als Carl |
 | Michael Douglas als Mr. Thompson |
 | Seth Rogen als Neil |
 | Amanda Detmer als Annie |
 | Ralph Ting als Toshi |
 | Todd Stashwick als Tony |
 | Bill Hader als Mark |
 | Lance Armstrong als Lance Armstrong |
| Jason Winer als Eddie |
 | Sidney S. Liufau als Paco |
 | Billy Gardell als Bartender Dave |
| Eli Vargas als Aaron |
| Houston Mack als Dougie |
| Bob Larkin als Army Veteran |
 | Suzanne Ford als Thompson's Secretary |
 | Claudia Choi als Carl's Secretary |
 | Summer Altice als Stripper |
| Jeanine Hass als Stripper |
| Peter Ruocco als Wedding Planner |
 | Joe Russo als Personnel Manager |
| Lance Irwin als Neighborhood Father |
 | Fenessa Pineda als 2nd Grade Girl |
 | Mario Revolori als 2nd Grade Boy |
| Jay Lembeck als Minister |
| Gil Harris als Reese |
 | Pat Crawford Brown als Aunt Kathy |
 | Bayani Ison als Hawaiian Bartender |
| Joe Wilson als Joe |
| Blaine Pate als Larry |
 | Kevin Breznahan als Charlie |
| Trevor Stock als Herb |
| Sean Perrone als Ned |
 | Craig Hosking als Pilot |
 | Harry Dean Stanton als Curly (uncredited) |
 | Amber Hay als Wedding Guest (uncredited) |
| Kepa Kruse als Waiter (uncredited) |
 | Michelle Lee als Hawaiian Air Ticketing Agent (uncredited) |
| May Porter als Waitress (uncredited) |
 | Tasha Smith als Co-Worker (uncredited) |
| Karen Patch | Costume Design |
| Sean Perrone | Executive Producer |
| Scott Stuber | Producer |
| Barbara Munch | Set Decoration |
| Anthony Russo | Director |
| Barry Robison | Production Design |
| Theodore Shapiro | Original Music Composer |
| Debra Neil-Fisher | Editor |
| Joe Russo | Director |
| Deborah Aquila | Casting |
| Aaron Kaplan | Executive Producer |
| Michael Fottrell | Executive Producer |
| Owen Wilson | Producer |
| Peter B. Ellis | Editor |
| Michael LeSieur | Screenplay |
| Charles Minsky | Director of Photography |
| Tricia Wood | Casting |
| Mary Parent | Producer |
| Kevin Constant | Supervising Art Director |
| Paul Sonski | Art Direction |
| Elaine Perlmann | Assistant Costume Designer |
| Medusah | Hair Department Head |
| Paula Hong | Hairstylist |
| Denise Dellavalle | Key Makeup Artist |
| Kimberly Greene | Makeup Department Head |
| Hasmig Karaciosian | Seamstress |
| Jennifer Carno | Script Coordinator |
| Patricio M. Farrell | Assistant Art Director |
| Bob Skemp | Greensman |
| Vickie Mynes | Key Hair Stylist |
| Joey Genitempo | Set Painter |
| Libby Morris | Set Decoration Buyer |
| Josh Lusby | Set Designer |
| Paul Detlefson | Set Dresser |
| Chris Samp | Standby Painter |
| Roy Seeger | First Assistant Sound Editor |
| Carl Fischer | Boom Operator |
| Benjamin Beardwood | Dialogue Editor |
| Bob Beher | Foley Supervisor |
| Thom Brennan | Foley Editor |
| Shawn Murphy | Scoring Mixer |
| Andrew Spencer Dawson | Sound Editor |
| Jason Leib | Post Production Supervisor |
| Catherine S. McComb | Production Supervisor |
| Michael Fottrell | Unit Production Manager |
| Ron Bolanowski | Special Effects Coordinator |
| Andrew Tucker | 3D Artist |
| Bob Roe | First Assistant Director |
| Liliana M. Molina | Script Supervisor |
| Jimmy N. Roberts | Stunt Coordinator |
| Lesley Aletter | Utility Stunts |
| Brian T. Pitts | Additional Camera |
| Cliff Fleming | Aerial Coordinator |
| Palma Bellardoni | Art Department Coordinator |
| Mario Cisneros | Grip |
| Ronald R. Koch Jr. | Lighting Technician |
| James Keys | Rigging Gaffer |
| Jose F. Barrios | Rigging Grip |
| Fumi Mashimo | Animation Supervisor |
| Jennifer L. Smith | Casting Associate |
| Bruce DiValerio | Construction Coordinator |
| Michael Eaves | Digital Color Timer |
| Ryan Helsley | Digital Intermediate |
| Fermin Davalos | Location Scout |
| Rodolfo Damaggio | Production Illustrator |
| George Doering | Musician |
| Marco Baccicalupi | Driver |
| Fred Teague | Transportation Captain |
| Ken Sale | Transportation Co-Captain |
| Greg Sanger | Leadman |
| Alyssa Evans | Production Coordinator |
| Michael Rayle | Cableman |
| Tommy Tomlinson | Property Master |
| Steve Burnes | Propmaker |
| Dayne Ahuna | Craft Service |
| Victor Lozano | Marine Coordinator |
| Anthony Woods | Set Medic |
| Carlo Pratto | Post Production Accountant |
| Donna Glasser-Hancock | Production Accountant |
| Patti Hawn | Publicist |
| Valerie Johnson | Set Production Assistant |
| Bruce Tanis | Sound Effects Editor |
| Petur Hliddal | Sound Mixer |
| Jack Snyder | Sound Recordist |
| Robert Castro | Stand In |
| Lance Ashton Slaton | Storyboard Artist |
| Maxine Abarbara | Studio Teacher |
| Steven D. Williams | Supervising Sound Editor |
| Jim Dunbar | Thanks |
| Michelle LeDoux | Best Boy Electric |
| Michael C. Price | Key Grip |
| Sam Seig | First Assistant Editor |
| Randall Poster | Music Supervisor |
| Sal Alvarez | Camera Loader |
| Thad Beier | Visual Effects Supervisor |
| Sean Thompson | Additional Editor |
| Collin Fowler | Visual Effects Coordinator |
| Jesse Olivares | Video Assist Operator |
| Tony Blondal | Orchestrator |
| Hilary Niederer | Costumer |
| Amy Jo Hoppenfeld | Key Costumer |
| Melissa Brockman | Visual Effects Producer |
| Josh Ian Elliott | On Set Dresser |
| Dominic Gherardi | Tailor |
| Bernie Bonner Axelrod | Second Second Assistant Director |
| P. Scott Sakamoto | Camera Operator |
| Adam Davidson | Second Unit Director |
| Danny Ault | Electrician |
| Carolyn Lassek | Assistant Property Master |
| Louie DeMarco | First Assistant "B" Camera |
| Jason Sweers | Graphic Designer |
| Melissa Moseley | Still Photographer |
| Catherine Leyba | Set Decorating Coordinator |
| Douglas J. Stewart | Textile Artist |
| Andrea Horta | ADR Editor |
| Jeff Gomillion | ADR Mixer |
| Philip Rogers | ADR Recordist |
| Charlene Amateau | Costume Supervisor |
| Lisa D. Quercioli | Set Costumer |
| Dawn Fintor | Foley Artist |
| David Betancourt | Foley Recordist |
| Curtis Collins | Location Manager |
| Andrew Silver | Music Editor |
| David E. Diano | "B" Camera Operator |
| Landon Ruddel | Best Boy Grip |
| John A. Brubaker | Transportation Coordinator |
| Eric Budlong | Dolly Grip |
| Tommy Klines | First Assistant "A" Camera |
| Dale White | Second Assistant "A" Camera |
| Scott Whitbread | Second Assistant "B" Camera |
| Marcos O. Lopez | Second Assistant Camera |
| Caitlin McKenna | ADR Voice Casting |
| Erin Toner | Casting Assistant |
| Mark Sachen | Colorist |
| Mary Beth Smith | Negative Cutter |
| Bruce Babcock | Conductor |
| Stephen Coleman | Music Programmer |
| Alexandra Ward | Art Department Production Assistant |
| Kirby Adams | First Assistant Accountant |
| Steve Reinhardt | Assistant Chief Lighting Technician |
| Carrie Oyer | Assistant Production Coordinator |
| James A. Lundin | Base Camp Operator |
| Chris Ryan | CG Artist |
| Jeff Murrell | Chief Lighting Technician |
| Tammy L. Smith | Extras Casting |
| Michele LaBrucherie | Key Set Production Assistant |
| Amy Denning Winfrey | Payroll Accountant |
| Adam Courier | Production Assistant |
| Mark Kurzweil | Second Assistant Accountant |
| David Christopher Campbell | Construction Foreman |
| Dick Ziker | Stunts |
| Dean Wolcott | Set Designer |
| Helena Barrett | Stunts |
| Erik Rondell | Stunts |
| Tanoai Reed | Stunts |
