“Chasing October” features filmmaker Matt Liston, who quits his job to single-handedly will the Chicago Cubs to a 2003 World Series win through a documentary. Blurring the lines between comedy and heartfelt devotion, the film captures Liston in the bleachers during pivotal games and includes interviews with not only Cubs players like Kerry Wood but also celebrities such as Bernie Mac, Gary Sinise, Joe Mantegna, Jeff Garlin, and Larry King.

As Liston’s passion project unfolds, it strains his personal life, leading to a breakup with his girlfriend, Faline England. Despite these challenges and the Cubs falling short of a World Series title, the film serves as a heartfelt, often comedic exploration of extreme fandom and enduring hope among Cubs supporters.

Chasing October | March 16, 2007 (United States) 8.3
Director: Matt ListonWriter: Gary Cohen, Matt ListonStars: Ben Brimer, Nathaniel O. Calloway, Hallie Faben ComfortSummary: Chasing October is filmmaker Matt Liston's docu-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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