
| Ben Affleck | ... | Narrator |
 | Glen Ordway | ... | Himself (WEEI Sports Radio, Boston) (as Glenn Ordway) |
 | Steven Wright | ... | Himself (Burlington, MA) |

| Michael Chiklis | ... | Himself (Andover, MA) |
 | Thomas Boswell | ... | Himself (Washington Post, Sports Columnist) |
 | Leigh Montville | ... | Himself (Boston Globe) |
 | Shaun Kelly | ... | Himself (Wellesly, MA) |
 | Jeffrey Sirkman | ... | Himself (Haverhill, MA) (as Rabbi Jeffrey Sirkman) |

| Mike O'Malley | ... | Himself (Boston, MA) |
 | Matt Wilson | ... | Himself (Wakefield, MA) |

| Denis Leary | ... | Himself (Worcester, MA) |
 | Glenn Stout | ... | Himself (Author, Red Sox Century) |
 | Robert W. Creamer | ... | Himself (Babe Ruth Biographer) (as Robert Creamer) |
 | Dan Shaughnessy | ... | Himself (Author, The Curse of the Bambino) |
 | Peter Casey | ... | Himself (Worcester, MA, Saw Ruth Play for Red Sox) |
 | Ben Mondor | ... | Himself (Owner, Pawtucket Red Sox) |
 | Harvey Robbins | ... | Himself (Chelmsford, MA) |
 | Richard Hanson | ... | Himself (Nashua, NH) |
 | Jeffrey Lyons | ... | Himself (Film / Theater Critic) |
 | Eddie Andelman | ... | Himself (WWZN Sports Radio, Boston) |
 | Kieran Meagher | ... | Himself (Reading, MA) |
 | Art Martone | ... | Himself (Providence Journal) |
 | Sean McAdam | ... | Himself (Providence Journal) |
 | Jerry Thornton | ... | Himself (Hanover, MA) |
 | Mark Leccese | ... | Himself (Boston, MA) |
 | Cheri Giffin | ... | Herself (Randolph, MA) |
 | Mike Barnicle | ... | Himself (96.9 FM Talk, Boston) |
 | Bob McGarry | ... | Himself (West Warwick, RI) |
 | Lenny Clarke | ... | Himself (Cambridge, MA) |
 | Bucky Dent | ... | Himself |
 | Dave Kruh | ... | Himself (Playwright, The Curse of the Bambino) |
 | Paul Giorgio | ... | Himself (Auburn, MA) |
 | Michael Wisseman | ... | Himself (Sunderland, MA) |
 | Kevin Kennedy | ... | Himself (Restoration Project, Acton, MA) |
 | Robert B. Parker | ... | Himself (Cambridge, MA) |
 | Richard A. Johnson | ... | Himself (Curator, Sports Museum of New England) |
 | Clark Booth | ... | Himself (Boston Journalist) |
 | Bud Collins | ... | Himself (Boston Globe) |
 | Edward Cossette | ... | Himself (Rochester, NH) |
 | Will McDonough | ... | Himself (1935-2003) |
 | Ted Sarandis | ... | Himself (WEEI Sports Radio, Boston) |
 | Howard Bryant | ... | Himself (Author, Shut Out: The Story Race and Baseball in Boston) |
 | Ouisie Shapiro | ... | Herself (Newton, MA) |
 | John McKeon | ... | Himself (Grafton, MA) |
 | Ben Birnbaum | ... | Himself (Brookline, MA) |
 | Jackie MacMullan | ... | Herself (Boston Globe) |
 | Paul Francis Sullivan | ... | Himself (Weston, MA) (as Paul Sullivan) |
 | John Tobin | ... | Himself (West Roxbury, MA) |
 | Scott Cordischi | ... | Himself (WSKO Sports Radio, Providence) |
 | Luke Salisbury | ... | Himself (Chelsea, MA) |
 | David Preziosi | ... | Young Babe |
| rest of cast listed alphabetically: |
 | Luis Aparicio | ... | Himself (archive footage) |
 | Wally Backman | ... | Himself (archive footage) |
 | Marty Barrett | ... | Himself (archive footage) |
 | Bill Buckner | ... | Himself (archive footage) |
 | Bernie Carbo | ... | Himself (archive footage) |
 | Gary Carter | ... | Himself (archive footage) |
 | Tony Conigliaro | ... | Himself (archive footage) |
 | Dwight Evans | ... | Himself (archive footage) |
 | Carlton Fisk | ... | Himself (archive footage) |
 | Jimmie Foxx | ... | Himself (archive footage) |
 | Denny Galehouse | ... | Himself (archive footage) |
 | Nomar Garciaparra | ... | Himself (archive footage) |
 | Tommy Harper | ... | Himself (archive footage) |
 | Ray Knight | ... | Himself (archive footage) |
 | Bill Lee | ... | Himself (archive footage) |
 | Jim Lonborg | ... | Himself (archive footage) |
 | Willie Mays | ... | Himself (archive footage) |
 | John McNamara | ... | Himself (archive footage) |
 | Kevin Mitchell | ... | Himself (archive footage) |
 | Tony Perez | ... | Himself (archive footage) |
 | Lou Piniella | ... | Himself (archive footage) |
 | Jim Rice | ... | Himself (archive footage) |
 | Jackie Robinson | ... | Himself (archive footage) |
 | Babe Ruth | ... | Himself (archive footage) |
 | Calvin Schiraldi | ... | Himself (archive footage) |
 | Vin Scully | ... | Himself (archive sound) |
 | Enos Slaughter | ... | Himself (archive footage) |
 | Bob Stanley | ... | Himself (archive footage) |
 | George M. Steinbrenner III | ... | Himself (archive footage) |
 | Dick Stuart | ... | Himself (archive footage) |
 | Mike Torrez | ... | Himself (archive footage) |
 | Mookie Wilson | ... | Himself (archive footage) |
 | Tom Yawkey | ... | Himself (archive footage) |