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One man quits everything to drag the Cubs to glory by sheer chaotic willpower.

Chasing October (2007)

delusional optimismsports cult energyDIY madness

Overview

ComedyDocumentary

"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.

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Content warning
obsession vs. realitycommunity and belongingthe absurdity of fandomAmerican dream mythology

Standout Aspects

Direction

Liston directing himself into increasingly absurd situations with zero self-awareness.

Writing

Narrative somehow treats a $20 million loan attempt as totally reasonable.

Production

Genuine all-access moments that no sane production would greenlight.

Best for:Friends: Watch with your most unhinged sports-obsessed friend who talks to the TV.·Solo: Late night when you need proof that passion can be completely unhinged.·Rewatch: Post-Cubs 2016 win — the context changes EVERYTHING.
M

Director

Matt Liston

ReleasedMar 23, 2007
Runtime1h 30m
StatusReleased

Vibe

Pacefast
Intensitymedium
Tonelight
Feelmedium
October Entertainment

Top Cast

Faline England

Faline England

Self

Bill Kurtis

Bill Kurtis

Narrator (voice)

Ask about Chasing October

Opens AI chat

Deep Dive

Trivia, insights & behind the scenes

Cultural

Made during the 108-year championship drought, this captures pre-2016 Cubs fandom as genuine religious trauma.

Trivia

Liston's 'Fan-Interference' campaign actually influenced real front office conversations, blurring documentary subject and participant beyond recognition.

Gallery

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