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Using the frame of opening day, 2006, this documentary examines the Cubs' 100 years without a World Series title. Between conversations with a half-dozen selected Cubs fans in 2006, the film looks back at the Wrigley years, sale to the Tribune, and coming oh-so-close in 1945, 1969, 1984, and 2003.
| Name | Character | Team | |
|---|---|---|---|
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Dennis Farina | Self - Narrator (voice) | Unowned |
| Ron Santo | Self | Unowned | |
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Ferguson Jenkins | Self | Unowned |
| Ryne Sandberg | Self | Unowned | |
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Michael Wilbon | Self | Unowned |
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Bob Costas | Self | Unowned |
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Jeff Garlin | Self | Unowned |
| Billy Williams | Self | Unowned | |
| Matt Liston | Self | Unowned |