Zen and the Art of Motorcycle Maintenance
Robert Pirsig

Road trip fun + philosophical musings = timeless classic.
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No Opportunity Wasted
Phil Keoghan

You'd be hard-pressed to find a better symbol of—and cheerleader for—living an adventurous life.
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Anne of Green Gables
Megan Follows
Directed by Kevin Sullivan

A Canadian classic for “kindred spirits.”
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Moonstruck
Cher, Nicolas Cage
Directed by Norman Jewison

Johnny Camorari (Cage): “Love don't make things nice—it ruins everything.”
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Rabbit-Proof Fence
Everlyn Sampi, Tianna Sansbury, Laura Monaghan
Directed by Phillip Noyce

Three Australian aboriginal girls walk 1,500 miles home.
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Raiders of the Lost Ark
Harrison Ford, Karen Allen
Directed by Steven Spielberg

Do I really need to explain this one?

Sabrina
Humphrey Bogart, Audrey Hepburn, William Holden
Directed by Billy Wilder

When I fell in love with Humphrey Bogart.
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Whale Rider
Keisha Castle-Hughes
Directed by Niki Caro

Who says women can't be leaders?
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Alias
Jennifer Garner, Michael Vartan
Created by J.J. Abrams

Whatever you do, don't skip the two-parter with Quentin Tarantino.
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Lost
Best Ensemble Cast on TV
Created by J.J. Abrams

Hottest group of castaways, ever.
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Wide Open Spaces
Dixie Chicks

The title track is especially fitting.