I'm not a big fan of watching movies over and over. but there are a few that would be on my list (as a child of the 80's, many are from that era):
Hoosiers
Grease
Sixteen Candles
Breakfast Club
Some Kind of Wonderful (I know EVERY, stinkin' word!)
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my boy cheering on the Mavs with his Mavs maraca and wearing his Jason Terry headband. 
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