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.