Fun!
In recent years, the movie I keep watching over and over is Arrival, with Amy Adams. It's a bit of a mystery, and rewards a re-watch. Love the music, too.
Older movies? All About Eve is wonderful.
Not quite so old, but a tv movie from the seventies that deserves to live on: Love Among the Ruins with Katharine Hepburn and Lawrence Olivier. Parts of it are a bit clunky and awkward, but there are some scenes that stand with the best of cinema in terms of screenplay. And her costumes are fabulous.
Holiday movies? I'm kinda burned out on the actual classics, so I tend to watch Trading Places (Eddie Murphy) and Die Hard, both set AT the holidays, if not about the season.
Still not ditching my dvds of the classics, though. I'll come back around. One I do always like to watch while baking cookies is The Homecoming with Patricia Neal, that started the whole Waltons phenomenon. This original movie is my favorite.
How could I forget The Princess Bride? Inconceivable.
And Soapdish is fun too.