Melancholia - just watched it again off the back of this thread. Disturbing, multi-layered, and open to so many interpretations. I love it, but it always leaves me feeling a bit bereft.
Then there's the original Fantasia (Disney) just delightful escapism and visual pyrotechnics :)
Two Christmas traditions - the Wizard of Oz, and Die Hard
The Adventures of Robin Hood (Errol Flynn, Olivia de Havilland) is brilliant - I watch it every couple of years just for the energy and the nostalgia of it all. Pirates of the Caribbean gives off a similar vibe, and that's another one I could watch multiple times.
Then there's Camelot, the musical - Richard Harris and Vanessa Redgrave - such a wonderful combination of great tunes, fantastic set pieces, and human tragedy.
If in the mood, the entire Lord of the Rings trilogy, plus the
Hobbit 'should-not-have-been-a-trilogy-but-on-balance-I-guess-you-can't-have-too-much-of-a-good-thing'.
Of course, The Princess Bride - best film ever made!