Matt Liston decided that quitting his job and making a documentary about his beloved Chicago Cubs in 2003 would break their curse and get them a World Series title for the first time since 1908. It didn’t quite work out that way, but he did make an enjoyable and memorable film in the process. Appearances by Bernie Mac, Gary Sinise, Joe Mantegna, Jeff Garlin, and Larry King.
Chasing October (2007) Documentary, Comedy, Sport | 1h 38min | 16 March 2007 (USA) 
8.4
8.4 
Director: Matt ListonWriters: Gary Cohen, Matt ListonStars: Ben Brimer, Nathaniel O. Calloway, Hallie Faben ComfortSummary: Chasing October is filmmaker Matt Liston's documentary-comedy that chronicles his crusade to take the Cubs to the World Series "by any means necessary." Liston quits his job and decides that by making a documentary about the team during the 2003 season, he can single-handedly will the Cubs to the post season. The hilarious film will bring joy to every Cubs Fan.
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