
| 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) |
If you liked the documentary, I suggest that you read the book by Dan Shaughnessy from which it is based. There is a lot more detail to the history of the Red Sox than what was depicted. Red Sox fans have been lead to believe that former owner Harry Frazee sold Babe Ruth to the Yankees simply to put on a Broadway musical. Although Ruth was a great player, he was not a team player. He was difficult and often abandoned the team to pursue his own interests. Frazee did not want to sell Ruth, but did not want a "one-man" team, which he saw the Red Sox turning into. This transaction changed the fortunes of two teams as the Yankees, who had never won anything before 1919, became contenders and champions almost overnight, while the Red Sox became forgettable. There is more to the Red Sox inability to win a championship than the sale of Babe Ruth. For example, the Red Sox had the opportunity to become the pioneers of integration when in 1945, Jackie Robinson and several other negro league players went to Fenway Park for a tryout and were soundly rejected. A few years later, Willie Mays was also rejected. In fact, the Red Sox did not have a black player until 1959. The hesitance of former owner Tom Yawkey to sign black players may have contributed to the Red Sox championship drought, as well as the fans obsession with the Yankees. Each chapter of the book covers various periods of Red Sox history, including the 4 World Series lost in 7 games and the strange occurrences in between, as well as the rivalry with the Yankees. I recommend the book to all baseball fans so that fact can be separated from hearsay.