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A ten-year-old CEO in a power suit? Corporate America finally found its perfect employee.
IMDb
65
Watch(US)

Bye Bye Benjamin (2006)

absurdist workplace satirekid-adult chaosmillennial anxiety precursor

Overview

Comedy

Benjamin Osgood, a savvy ten-year-old business executive, meets a coworker's daughter, and must decide how grown up he wants to be.

Flag of USUS
Content warning
short film

Standout Aspects

Acting

Ted Danson playing straight man to a child in a tie.

Direction

McDowell's debut already shows his deadpan surrealism.

Costume

Tiny business formal that somehow looks correct.

Best for:Streaming: Late-night weirdness when you need something unhinged but brief.·Solo: Nobody else will understand why you're watching this.·Background: Barely needs attention, rewards it anyway.
Charlie McDowell

Director

Charlie McDowell

ReleasedJan 31, 2006
Runtime22m
StatusReleased

Vibe

Pacefast
Intensitymedium
Tonemixed
Feellight
Budget$50K
AFI

Top Cast

Kelli Berglund

Kelli Berglund

Birthday Party Guest

Ted Danson

Ted Danson

Bill

Jason Segel

Jason Segel

Theodore Everest

Lolita Davidovich

Lolita Davidovich

Janet

Seymour Cassel

Seymour Cassel

Mr. Ruby

Taylor Baugh

Taylor Baugh

VP of Marketing

Paul Hipp

Paul Hipp

Vice President

Ask about Bye Bye Benjamin

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Deep Dive

Trivia, insights & behind the scenes

Trivia

Charlie McDowell later directed The One I Love and Windfall—his deadpan surrealism started here.

Cultural

Made in 2006, it prefigured the 'kid adult' anxiety of millennial burnout culture by a decade.

Reviews

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