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| Directed by | ||
|---|---|---|
 | Bobby Farrelly | |
 | Peter Farrelly | |
| Starring | ||
|---|---|---|
| Drew Barrymore | Lindsey | |
| Jimmy Fallon | Ben | |
| Jason Spevack | Ben - 1980 | |
| Jack Kehler | Al | |
| Scott Severance | Artie | |
| Jessamy Finet | Teresa | |
| Maureen Keiller | Viv | |
| Lenny Clarke | Uncle Carl | |
| Ione Skye | Molly | |
| KaDee Strickland | Robin | |
| Marissa Jaret Winokur | Sarah | |
| Evan Helmuth | Troy | |
| Brandon Craggs | Casey | |
| Brett Murphy | Ryan | |
| Isabella Fink | Audrey | |
| Miranda Black | Carrie | |
| Greta Onieogou | Tammy | |
| Johnny Sneed | Chris | |
| James Sikking | Doug Meeks | |
| Michael Rubenfeld | Ian | |
| Willie Garson | Kevin | |
| Armando Riesco | Gerard | |
| Zen Gesner | Steve | |
| Siobhan Fallon Hogan | Lana | |
| JoBeth Williams | Maureen Meeks | |
| Mark Andrada | Ezra | |
| Charlotte Sullivan | Spin Instructor | |
| Scott Desano | Binocular Guy | |
| Lizz Alexander | Charlene | |
| Shary Guthrie | Christie | |
| Don Gavin | Cop | |
| Andrew Wilson | Grant Wade | |
| Martin Roach | Husband | |
| Gina Clayton | Lady at Other Table | |
| Wayne Flemming | Leon | |
| Bobby Curcuro | Loiterer | |
| Bart Bedford | Man at Other Table | |
| Jason Varitek | Jason Varitek | |
| Johnny Damon | Johnny Damon | |
| Trot Nixon | Trot Nixon | |
| George King | Mr. Munsell | |
| Jackie Burroughs | Mrs. Warren | |
| John Boylan | Myerson | |
| J.C. Kenny | Reporter | |
| Paul McGuire | Reporter | |
| Quancetia Hamilton | Rita | |
| Ken Rogerson | Scalper | |
| Howard Nickerson | Usher | |
| Matt Watts | Valet | |
| George Ghali | Vern - Gym Teacher | |
| Andrea Davis | Wife | |
| Darren Frost | Zach | |
| Sharlene Yuen | Receptionist | |
| Geoffrey Williamson | High School Kid #1 | |
| Jim Rice | Jim Rice | |
| Dennis Eckersley | Dennis Eckersley | |
| Keith MacWhorter | Keith MacWhorter | |
| Melinda Lopez | Sheri | |
| Sam Dissanayake | Mr. Abdo | |
| Peter Gammons | Peter Gammons | |
| Steve Levy | Reporter at Spring Training | |
| Tim McCarver | Tim McCarver | |
| Don Orsillo | Don Orsillo | |
| Harold Reynolds | Harold Reynolds | |
| Bob Lobel | Bob Lobel | |
| Carl Beane voice | Stadium Announcer | |
| Mathew Peart | High School Kid #2 | |
| David Klar | High School Kid #3 | |
| Jermaine Plummer | High School Kid #4 | |
| Erin Nanstad | Female Fan | |
| Johnny Cicco | Bleacher Fan | |
| Brian Hayes Currie | Screaming Fan | |
| Danny Murphy | 1980's Vendor #1 | |
| Dan Cummings | 1980's Vendor #2 | |
| Daniel Greene | Waiter | |
| Jordan Leandre | Jordan Leandre | |
| Bob Weekes | Hot Dog Vendor #1 | |
| John Ruggiero | Hot Dog Vendor #2 | |
| Joe Buck | Sportscaster | |
| Joe Castiglione | Sportscaster | |
| Thomas Jordan | Kid in Cast | |
| Preston Thomas | 1980's Sox Player | |
| Scott Rosenberg | 1980's Sox Player | |
| Mark Ciardi | 1980's Sox Player | |
| Keegan O'Donnell | 1980's Batboy | |
| Emily O'Donnell | 1980's Fan | |
| Diana O'Donnell | 1980's Fan | |
| Meda Thomas | 1980's Fan | |
| Jack Andrade | 1980's Fan | |
| Warren Tashjian | 1980's Fan | |
| Ray Rocket Valliere | 1980's Fan | |
| Bob Sands | Landsdowne Street Fan | |
| Corey Sands | Landsdowne Street Fan | |
| Andrew Steedman | Landsdowne Street Fan | |
| Mike Steedman | Landsdowne Street Fan | |
| Davis Ballard | Landsdowne Street Fan | |
| Blair Ballard | Landsdowne Street Fan | |
| Stacey Lucchino | Landsdowne Street Fan | |
| Marla Angermeier | Landsdowne Street Fan | |
| Alison Novelli | Landsdowne Street Fan | |
| Mari Corcoran | Landsdowne Street Fan | |
| David Rosenberg | Party Animal | |
| Rick Cohen | Party Animal | |
| Jesse Peter | East Boston School Kid | |
| Abe Farrelly | East Boston School Kid | |
| Lucy Bidwell | East Boston School Kid | |
| Joan Macleod-Follows | Lindsey's Co-Worker | |
| Bobbi Stoller | Crazed Sox Fan | |
| Brad Blank | Crazed Sox Fan | |
| Todd Abbrecht | Crazed Sox Fan | |
| Monica Niedermeyer | Crazed Sox Fan | |
| Jenna Caswell | Crazed Sox Fan | |
| Amie James | Crazed Sox Fan | |
| Matt Melina | Crazed Sox Fan | |
| Jaime P. Ford | Crazed Sox Fan | |
| Christine Ford | Crazed Sox Fan | |
| Docky | Crazed Sox Fan | |
| Mariann Neary | Crazed Sox Fan | |
| Sam Caswell | World's Greatest Sox Fan | |
| Ron Puppy Cavallo | Bleacher Bum | |
| Paul Palandjian | Fenway Security | |
| Laurel Astri uncredited | Tom Boy Hockey Player | |
| Adam Bagni uncredited | Landsdowne Street Fan | |
| Eric Bruno Borgman uncredited | Red Sox Fan | |
| Janet Borgman uncredited | Red Sox Fan | |
| Brina uncredited | Crazed Sox Fan | |
| Jason Carlage uncredited | Red Sox Fan | |
| Shana Carr uncredited | Boston Red Sox Fan | |
| Michael Christopher Cole uncredited | 1980's Extra | |
| Rick Cordeiro uncredited | Red Sox Fan | |
| Patrick Cotnoir uncredited | Fan in Crowd | |
| John Currie uncredited | Fan | |
| Elisangela DiAlencar uncredited | Red Sox Fan | |
| D.J. Dierker uncredited | Voice | |
| Frank Durant uncredited | Hotel Guest | |
| Mark Falvo uncredited | Red Sox Fan | |
| Mugisha Feruzi uncredited | First Base Coach | |
| Brenda Flynn uncredited | Red Sox Fan | |
| Shawn Fogarty uncredited | Red Sox Fan at Fenway | |
| John Franchi uncredited | Red Sox Fan | |
| Lorre Fritchy uncredited | Extra | |
| Ken Gagne uncredited | Red Sox Fan | |
| Russ Jaquith uncredited | Red Sox Fan | |
| John Eliot Jordan uncredited | Self | |
| Grady Justice uncredited | Red Sox Fan | |
| Glenn W. Kane uncredited | Red Sox Fan | |
| Stephen King uncredited | Stephen King | |
| Stephen Kyle uncredited | Usher / Fan | |
| Michael M Luzzi uncredited | Boston Red Sox Fan | |
| Robert Mason uncredited | Red Sox Fan | |
| Alexandra McDougall uncredited | Red Sox Fan | |
| Paul McGillicuddy uncredited | Boston Red Sox Fan | |
| Matthew Nagle uncredited | Cardinal Stadium Seating at World Series Game | |
| Ed OKeefe uncredited | Red Sox Fan | |
| John Olerud uncredited | John Olerud | |
| Angela Palmer-Haibach uncredited | 70's Flashback Fan | |
| Tracy Parris uncredited | Red Sox Fan | |
| Anthony M. Pizzuto uncredited | Red Sox Fan | |
| John Pungitore uncredited | Red Sox Fan | |
| Nicholas Purcell uncredited | Red Sox Fan | |
| Jerry Quinn uncredited | Ball Park Usher | |
| Ralph Regine uncredited | 1980's Red Sox Fan | |
| Steve Scarfo uncredited | Red Sox Fan | |
| Cher Scarlett uncredited | Red Sox Fan | |
| Michael Sercerchi uncredited | Bar Patron | |
| Joe Sobalo Jr. uncredited | Red Sox Fan | |
| Stream uncredited | Red Sox Fan | |
| Tom Whalen uncredited | Red Sox fan | |
| Kris Williams uncredited | Kris Williams | |
| Darryl Wooten uncredited | Red Sox Fan | |
| Jeanne Zelasko uncredited | Jeanne Zelasko | |
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Canada release date: 8th April 2005 United States release date: 8th April 2005 United Kingdom release date: 12th August 2005
Ireland release date: 12th August 2005
Turkey release date: 12th August 2005
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