When record store owner and compulsive list-compiler Rob Gordon gets dumped by his long-time girlfriend, Laura, because he hasn't changed since they met, he revisits his top five breakups of all time in order to figure out what went wrong. As he examines his failed attempts at romance and happiness, the process finds him being dragged, kicking and screaming, into adulthood.
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| Art | Thérèse DePrez | Production Design |
| Camera | Seamus McGarvey | Director of Photography |
| Production | Victoria Thomas | Casting |
| Writing | Scott Rosenberg | Screenplay |
| Directing | Stephen Frears | Director |
| Writing | D.V. DeVincentis | Screenplay |
| Writing | Steve Pink | Screenplay |
| Production | Rudd Simmons | Producer |
| Production | Tim Bevan | Producer |
| Art | David Chapman | Production Design |
| Writing | John Cusack | Screenplay |
| Sound | Howard Shore | Original Music Composer |
| Editing | Mick Audsley | Editor |
| Directing | Jeffrey Wetzel | First Assistant Director |
| Directing | Aiman A. Humaideh | Second Assistant Director |
| Sound | Peter Joly | Supervising Sound Editor |
| Art | Larry Lundy | Set Decoration |
| Sound | Michael Redfern | Foley Editor |
| Sound | Clare Mahoney | Foley Artist |
| Production | Mike Newell | Executive Producer |
| Directing | Chiemi Karasawa | Script Supervisor |
| Sound | Jason Swanscott | Foley Artist |
| Sound | Carl Fischer | Boom Operator |
| Crew | Chris Nolte | Stunt Double |
| Production | Tarn Harper | Post Production Accountant |
| Costume & Make-Up | Gina Panno | Costumer |
| Art | Timothy W. Tiedje | Property Master |
| Production | Kim Taylor-Coleman | Casting Associate |
| Sound | Petur Hliddal | Sound Mixer |
| Art | Joel Prihoda | Leadman |
| Sound | Danny Longhurst | Dialogue Editor |
| Production | Liza Chasin | Executive Producer |
| Sound | Kathy Nelson | Music Supervisor |
| Sound | Adrian Rhodes | Sound Re-Recording Mixer |
| Sound | Diane Greaves | Foley Artist |
| Costume & Make-Up | Jeanne Van Phue | Key Makeup Artist |
| Art | Derrick Kardos | Graphic Designer |
| Production | John Cusack | Co-Producer |
| Art | Nicholas Lundy | Art Direction |
| Costume & Make-Up | Jennifer Jobst | Costume Supervisor |
| Production | D.V. DeVincentis | Co-Producer |
| Production | Billy Higgins | Unit Production Manager |
| Production | Joan Altman | Production Accountant |
| Costume & Make-Up | Phillip Ellman | On Set Dresser |
| Crew | Susan Hegarty | Dialect Coach |
| Sound | Ted Swanscott | Foley Mixer |
| Production | Steve Pink | Co-Producer |
| Production | Demetra Diamantopoulos | Location Manager |
| Lighting | Robert Swander | Best Boy Electric |
| Sound | Terry Isted | Foley Mixer |
| Sound | Michael Higham | Supervising Music Editor |
| Production | Wendy Weidman | Casting Associate |
| Camera | Melissa Moseley | Still Photographer |
| Sound | Joe Lisanti | Music Editor |
| Production | Alan Greenspan | Executive Producer |
| Camera | David Morenz | First Assistant Camera |
| Costume & Make-Up | Heather Pollock | Costumer |
| Art | Terry Baughman | Construction Coordinator |
| Crew | Rick LeFevour | Stunt Coordinator |
| Crew | Tania Blunden | Post Production Supervisor |
| Production | Brendan Donnison | ADR Voice Casting |
| Sound | Shari Johanson | Music Editor |
| Camera | Art Bartels | Key Grip |
| Editing | John Stanborough | Color Timer |
| Crew | A. Welch Lambeth | Transportation Coordinator |
| Crew | Will Gatlin | Craft Service |
| Writing | Nick Hornby | Novel |
| Production | Joan Philo | Extras Casting |
| Crew | Edward J. Reardon | Set Medic |
| Production | Emma Thomas | Producer's Assistant |
| Crew | Robert Byrnes | Set Medic |
| Crew | Michael Cronin | Set Medic |
| Crew | Patricia Newby | Set Medic |
| Production | Anne Johns | Production Coordinator |
| Directing | Anne Berger | Second Second Assistant Director |
| Production | Anita Brongiel | Production Secretary |
| Production | Deborah Evans | Payroll Accountant |
| Camera | Chad Erickson | Camera Intern |
| Costume & Make-Up | Margaret Morettini | Assistant Costume Designer |
| Camera | William R. Nielsen Jr. | Camera Operator |
| Crew | Thomas Coe | Stunt Double |
| Production | Margaret J. Orlando | Assistant Production Coordinator |
| Costume & Make-Up | Laura Connolly | Key Hair Stylist |
| Sound | Mark Rose | Assistant Sound Editor |
| Art | Michael D. Gianneschi | Assistant Property Master |
| Editing | Mags Arnold | First Assistant Editor |
| Crew | Louise Spencer | Unit Publicist |
| Crew | Elizabeth Miller | Loader |
| Production | Andy Wheeler | First Assistant Accountant |
| Camera | Daniel W. Fuller | Second Assistant Camera |
| Sound | Jeffrey A. Williams | Utility Sound |
| Editing | Kate Higham | First Assistant Editor |
| Lighting | James A. Miller | Gaffer |
| Costume & Make-Up | Laura Bauer | Costume Designer |
| Production | Adrienne Swan | Second Assistant Accountant |
| Costume & Make-Up | Naomi Donne | Makeup & Hair |
| Production | Claire Simon | Casting |
| Production | Adam Graham | Location Assistant |
| Production | Joanna S. Frank | Production Assistant |
| Production | Ed Portoghese | Production Assistant |
| Camera | Fernando M. Briones | Dolly Grip |
| Production | Jennifer Baron | Assistant Location Manager |
| Crew | Sam Barkan | Special Effects Coordinator |
| Production | Melissa Sadoff | Producer's Assistant |
| Production | John David Wolfe | Location Assistant |
| Production | Jon Schluenz | Production Assistant |
| Sound | John Cusack | Music Supervisor |
| Crew | William T. Hogan III | Transportation Coordinator |
| Sound | Steve Pink | Music Supervisor |
| Camera | Michael Lange | Best Boy Grip |
| Sound | Doug Dearth | Music Coordinator |
| Production | Eric H. Heisner | Production Assistant |
| Production | David Malley | Production Assistant |
| Production | Adam Rosen | Production Assistant |
| Production | Dan Koretzky | Production Consultant |
| Sound | D.V. DeVincentis | Music Supervisor |
| Production | Juliette Dow | Producer's Assistant |
| Production | Anne Devereux | Producer's Assistant |
| Production | Kenneth w. Bradley | Production Assistant |
| Production | Jeff Sternberg | Production Assistant |
| Crew | Gareth Jones | Score Engineer |
| Production | Dawn Patch | Production Assistant |
| Crew | Ed Rak | Score Engineer |
| Production | Veloz Gomez | Production Assistant |
