I tend to be a "one and done" type. Once I've seen a movie and I know how it ends, watching it again is pointless (to me)... especially "whodunit" movies or any movie with a plot twist or surprise ending... (do you see dead people? )
The only movie I have watched repeatedly is The Wizard of Oz. It used to be on TV once a year when I was a kid, and I watched it every year. I've seen it maybe 20-25 times in my life. And yeah, I still get a kick out of it even though I have almost the whole script memorized at this point!
There are a very small handful of movies that I have specifically made an effort to see more than once, but very few.
Escape From Alcatraz (starring Clint Eastwood)
Road to Perdition (Tom Hanks, Paul Newman)
The Verdict (Paul Newman)
The Outlaw Josie Wales (Eastwood again)
The Blues Brothers
Titanic (because of the absolutely fantastic effects and attention to period detail in every way)
That's about it as far as me watching the same movie more than once.