I'll bite. Jeez...that's a tough one. I never get tired of watching the following: 
 
 Fargo
 Gimme Shelter
 LA Confidential
 Sixteen Candles
 Pulp Fiction
 Little Miss Sunshine
 Lost in Translation
 Freeway
 Almost Famous
 Kill Bill 1
 
 Of course I love all the usual classics: Rear Window, Psycho, Some Like It Hot, Goodfellas, Taxi Driver, Full Metal Jacket, Scarface, and then some off-the-beaten-path flicks: Next Stop Wonderland, Clay Pigeons, With a Friend Like Harry, etc. True fact: I've never seen Gone With the Wind, and I've never sat through the Wizard of Oz in its entirety.