It would have to be anything by Sergio Leone, first. Ennio Morricone created some of the best movie soundtracks ever also. Leone was smart to use him. Man With No Name trilogy, Once Upon a Time in America/West, Nuovo Cinema Paradiso... great stuff. I also love all the Wes Anderson movies. And yes, Citizen Kane is one of my favorites. I hated it the first time I watched it... but after watching it again and again... it is really something else. Anything with directed by or staring Clint Eastwood... Unforgiven and Gran Torino are great. High Plains Drifter is also good. I've seen Ten Commandments and The Sound of Music a million times as a kid, so those are on the list. I've also seen Brother Sun, Sister Moon far too many times. It is really kinda lame, but it has to be on my list. Sappy movies include The Notebook (I cry nearly everytime I watch it at the end) Atonement and Amelie. Other movies that are great are: Groundhog Day, 2001, Lawrence of Arabia, Cast Away, Airplane, Some Like It Hot, Bad Santa, Slingblade, Shawshank, Great Expectations (the 1946 one), The Wizard of Oz, Casino, V for Vendetta, Rambo: First Blood (as a commentary on post-Vietnam war), Casablanca, Breakfast at Tiffany's and A Night at the Roxbury.