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A teenager bets his whole year on hope—did democracy deliver or break his heart?

Mile High: How to Win... and Lose... the White House (2009)

political coming-of-age2008 nostalgia tripearnest chaos

Overview

Documentary

A teenager who has spent a year of his life campaigning for Barack Obama makes his way to Denver to hear the former Presidential candidate accept his nomination.

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Content warning

Standout Aspects

Acting

Dan Rather and Tim Russert's final on-screen political commentary

Direction

Intimate access to convention floor chaos and teenage vulnerability

Editing

Juxtaposes epic political theater with one kid's crushing expectations

Best for:Solo: Late-night reflection on when you believed in politics·Streaming: Short enough to squeeze between doomscrolling sessions·Friends: Debate if 2008 energy was real or manufactured
Heads up:Emotional: Russert died weeks after filming; carries unintentional elegiac weight
C

Director

Cassandra Nichols

ReleasedJan 1, 2009
Runtime1h 12m
StatusReleased

Vibe

Pacesteady
Intensitymedium
Tonemixed
Feelmedium
Ether Films

Top Cast

Dan Rather

Dan Rather

Self

Tim Russert

Tim Russert

Self

Joe Scarborough

Joe Scarborough

Self

Pat Buchanan

Pat Buchanan

Self

Ron Paul

Ron Paul

Self

Dennis Kucinich

Dennis Kucinich

Self

Ask about Mile High: How to Win... and Lose... the White House

Opens AI chat

Deep Dive

Trivia, insights & behind the scenes

Cultural

Shot during the 2008 DNC in Denver, capturing the last pre-social media presidential campaign where hope felt like a tangible commodity.

Memorable

Tim Russert's interview was his final on-camera appearance before his sudden death June 13, 2008—making this an accidental time capsule of pre-Trump political media.

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