I'm a fan of the Criterion Collection, especially some of their DVD artworks. I don't own any myself but having a library system with a whole bunch of them really helps. Anything released on Criterion can either bring out the film snob in some people or just the sheer enjoyment of relishing in a film that you love especially with the Criterion touch (quality and quantity). These are my faves.
1. Brief Encounter (1945)
This film is really one of the most poignant and tender films about elicit love that you could ever see. I loved it the first time I saw it, it's the essential David Lean and the cover speaks for itself.
2. Le Notti Bianche (1957)
The cover to this wonderful romantic Italian film from Luchino Visconti captures the essence of the film, the loneliness that comes from unrequited love. You can see it in the two characters countenance, not facing each other.
3. The Red Shoes (1948)
The Archers masterpiece. Excluding the beads of sweat on Moira Shearer's forehead, this is a face of confliction - perfectly captured here.
4. All That Heaven Allows (1955)
I love Douglas Sirk's romantic Technicolors of the 50's especially since Rock Hudson was in quite a few. This shows the isolation the two leads feel in the movie but they also look content gazing out the window.
5. Night Train to Munich (1940)
Not as known as it should be. I like this film for it's semi-comic moments, the jealousy Paul Henreid's character has towards Rex Harrison (you took Margaret Lockwood from him!) and it's adventures on a train and through the Alps. The cover has that comic-book(ish), old-theater card thing going on, is the best way I can describe it.