Oooh this is fun OK
Brokeback Mountain...because being stuck on a deserted island isnt depressing enough
Kiss Kiss Bang Bang
Its A Wonderful Life
The Color Purple
Eternal Sunshine
Moulin Rouge
Me and You and Everyone We Know
Y Tu Mama Tambien
Mystic River/Gone Baby Gone (yeah its cheating so sue me...theyre both Denis Lehane adaptations)
There Will Be Blood
Sunset Boulevard
Finding Nemo
Romy and Michelle's High School Reunion
Titanic (Screw all the skeptics this movie still keeps me entertained despite coming on cable every Saturday, I think its safe to say its with stood the test of time)
Bad Education
Maria Full of Grace
Shortbus
Modern Times (If only to watch the mechanical feeding machine scene over and over)
Before Sunset
City of Men
Film I'd throw into the water even if it was the only movie on a deserted island: Tie Casablana & Citizen Kane
I also dont think its fair to say a film cant be considered a masterpiece just because its not old. For example, movies like Brokeback, Eternal Sunshine, and Maria Full of Grace ive watched multiple times even though they've only been out a couple years, and each time theyve had the same impact on me as before. I've also watched Eli Sunday's sermon in There Will Be Blood about a million times now and I still get chills down my spine. On the other hand I've seen Citizen Kane twice. The first time I fell asleep, the second time I stayed awake and have never been happier when a movie ends.