There are only a handful of movies that I can watch over and over, but I'm always looking for more.
Here's my list, in no particular order...
Speed Racer
I really like the way that the majority of the story is revealed through flashbacks and non-linear storytelling. The visuals are bright and colorful, the dialog is smart, and the action is somewhere between cartoonish and sci-fi. I can watch this movie anytime.
The Princess Bride
One of the all-time great comedy fantasy and meme-rich movies of all time. I'll admit, I was a little put off by the grandpa-reads-to-the-kid wrapper around the story the first time I watched it, but it's never bothered me since.
Pixels
It took a long time for me to watch this movie because I had heard so many bad things about it, but when I finally did watch it I was blown away. I can't explain it, but I loved this movie. Maybe it's because I was there, 3,000 years ago in the 80's, but something about this move really struck a chord with me.
Big Trouble in Little China
There's no other movie I can think of that has so many quotable lines, and Kurt Russell is amazing in this move. The settings and the cast give this movie an eerie, mystical feel while preserving an amazing level of comedy and action that make this move fun to watch over and over again.
There are probably a few others that I can't think of right now, but I'll post more as I think of them.
What movies can you watch over and over?