Chasing October (2007)

"Chasing October" is a docu-comedy that chronicles one fan's crusade to take the Chicago Cubs to the World Series "by any means necessary." Director Matt Liston quits his job, gets all access to his favorite team, and rallies a city. Perhaps no other fan in the history of sports has gone to such an extreme. See Liston as he helps facilitate a trade, attempts to get a $20 million loan to help team payroll, and takes being a fan to a whole new level. This film is a hilarious must-see for all sports fans and for anyone who has ever chased a dream.