Chasing October is a docu-comedy that follows one fan's crusade to take the Chicago Cubs to the World Series "by any means necessary." The film documents how director Matt Liston quits his job and begins to rally a city on his shoulders to support the Cubs.
In the movie, Liston says that in a dream he was visited by Harry Caray, who is seated at a bar and is wearing a World Series ring. At this point, he knows what he must do — get his Cubbies to the World Series. Enlisting his best friend Chris Karnak to do the filming, he begins his Quixotic crusade.
As any Cubs fan can attest, if you want to be a Cubs fan you gotta learn to bleed blue and 2003 was no different. Armed with his savings and a bunch of credit cards, Liston coined the term "Just Believe," had it printed on memorabilia, and started giving it away.
The main characters in the film are of course Matt Liston, Chris Karnak, Matt's girlfriend Faline England, and Chris's girlfriend Allison, who became his wife on the day that the Cubs clinched the division. It also features appearances by Bernie Mac, Gary Sinise, Joe Mantegna, and Larry King. It has interviews with many of the Cubs players at the time such as Kerry Wood, Moises Alou, and Mark Prior, as well as Cubs legends Ernie Banks and Ryne Sandburg.
Chasing October works because it is not a slickly produced piece. It is rough around the edges. It shows that other people in Matt's life see him as being irresponsible, as being a bit of a nut case. His parents are clearly worried about him and his girlfriend leaves him after questioning him as to who ranks higher, her or the Cubs.
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