I'm very particular about the kinds of movies I watch, but there are certain movies that have this quality about them. They either make an important commentary about life, portray someone growing up/growing wise, have insightful, poignant lines, or are the delightful echoes of that deeply romantic part of me...

Movies I own and have watched a hundred times:
Little Women (Winona Ryder, 1994)
Holiday Inn (Bing Crosby and Fred Astaire, 1942)
Mansfield Park (1999)
Sense & Sensibility (Emma Thompson, 1995)
Anne of Green Gables (Megan Follows, 1986)
Anne of Avonlea (Megan Follows, 1987)
It's a Wonderful Life (James Stewart, 1947)
Pride & Prejudice (Collin Firth, 1996)
While You were Sleeping (Sandra Bullock, 1995)
Sabrina (Harrison Ford, 1995)

Movies I've watched a hundred times and would love to own:
Persuasion (Amanda Root, 1995)
Sabrina (Humphrey Bogart, 1954)
Parent Trap (both versions)
First Knight (Sean Connery, 1995)
Braveheart (Mel Gibson, 1995)
Clue (Eileen Brennan, Tim Curry, 1985)
Groundhog's Day (Bill Murray, 1993)

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