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A 2.0-rated mob comedy so chaotic it circles back to legendary.
TMDB
20

Chasing Robert (2007)

DIY disasterpieceChicago gritdesperate man energy

Overview

Comedy

Alan is a gambler desperate to erase the huge sports debt he owes to a cruel but quirky Chicago mobster.

Flag of USUS
Content warning
homophobiagamblingcompulsive gamblinggambling debt
toxic masculinity spiralsdebt as identityfailed redemption arcs

Standout Aspects

Acting

Richard Jeni's final film role, gloriously unhinged.

Practical Effects

Genuine Chicago locations shot on a shoestring and prayer.

Writing

Director casting himself as lead: narcissism or necessity?

Best for:Solo: Irony-poisoned night when you want to feel alive again.·Friends: Group viewing for maximum roasting potential.·Rewatch: Annual tradition once it becomes your whole personality.
Heads up:Language: 2007 casual homophobia played for uncomfortable laughs.·Triggers: Gambling addiction depicted without actual insight or growth.
L

Director

Len Austrevich

ReleasedJul 17, 2007
Runtime1h 29m
StatusReleased

Vibe

Pacefast
Intensitymedium
Tonemixed
Feellight
Budget$1M

Top Cast

Richard Jeni

Richard Jeni

Rich the Bookie

Rick Overton

Rick Overton

Thadeus Wrazinski

Dana Gould

Dana Gould

Therapist

Larry Miller

Larry Miller

Peter Vondra

Richard Portnow

Richard Portnow

Ed Thorton

Andy Dick

Andy Dick

The Wire

Michael Rivkin

Michael Rivkin

Toadie

Lin Shaye

Lin Shaye

Martha the Bookie

Dan Castellaneta

Dan Castellaneta

Dan the Bookie

Ask about Chasing Robert

Opens AI chat

Deep Dive

Trivia, insights & behind the scenes

Cultural

Shot during Chicago's mid-2000s indie boom, when digital filmmaking let anyone become a director—including this guy.

Memorable

Richard Jeni died by suicide months after filming; his performance as Rich the Bookie became an accidental elegy for a brilliant career cut short.

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