Hard one, I usually have more than one movie that comes to my mind, because they all serve different moods and situations - like if I want something deep and meaningful or just some popcorn action movie.
But here are three of my favorites that came to mind:
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Wonder Boys: Wonderful movie from 2000 with Michael Douglas as a writer unable to finish his second novel (after the huge success of his first one). Liked it very much because it had a firm grasp on the special kind of people who are artists as well as on the creative process.
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LoveActually: Great portmanteau film over the holiday season (Christmas/New Year) that proves it's premise that love is actually all around.
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Drei Nüsse für Aschenbrödel: In my opinion still the best movie take ever on the Cinderella fairy tale. It is an old fairy-tale film from 1973, co-produced by Czechoslovakia and East Germany. The title translates to 'Three Nuts for Cinderella', though I've heard it was published under the English titles of 'Three Gifts for Cinderella' and 'Three Wishes for Cinderella'. This movie has gorgeous costumes and landscapes and Cinderella is a rather strong woman, very unlike your run-of-the-mill damsel in distress that most Disney princesses have been for many years. I don't know how the English dubbed versions hold up, but the movie is regarded a classic in many European countries and again is traditionally on the air during the holiday season. If you still like fairy tales even outside of animated movies, this is one gem you should look at.
I've heard the Czech film archive is currently working on a digital restoration of the movie, thanks to funding from Norway. With some luck we will see the film in even better quality this year's holiday season (if they make it on time).
