I do, and many are already mentioned. Movies liike “The Sting”, “No Way Out”, or “The Sixth Sense” can be enjoyed twice. The first time when you don’t know the twist, the second when you do. Have only seen “Usual Suspects” once though.
Monty Python and the Holy Grail, seen it about 100 times. Never get tired of it.
Manos the Hands of Fate: fun to watch with new groups of friends and torture them with it.
Who Framed Roger Rabbit: Nearly drove my mother insane when I was a kid, watching this on VHS over and over and over. Now I have it on DVD and enjoy rewatching it from time to time.
Meet The Parents: Dumb, painful comedy but I love it.
Billy Madison: Like MtP but even dumber and I love it even more. I can practically quote the entire movie (and got kicked out of photography class one day in HS for it, in fact).
There are many more movies I’ve seen more than once and several I’ve watched probably close to a dozen times.
There are some movies that are like comfort food to me. Mostly old Disney movies. Some of the Pixar movies.
A few others:
Jurassic Park
Stardust
Big Fish
LOTR
Nightmare Before Christmas
The first two X-Men movies
Sleepy Hollow
As a kid, I must have watched the He-Man and She-Ra movie a dozen times. My dad never understood why my brother and I insisted on re-renting that video so often. I found it on Youtube recently and watched it with a friend of mine. As an adult, it is unintentionally hilarious.
As a general rule I don’t watch even a good movie more than twice. Most aren’t going to provide any new thrills after that first viewing. Some do require a follow-up or two to be sure all the plot details make sense. And a precious few are just too good as movies to be satisfied with the one viewing.
But the ones I keep going back to, usually when they pop up in the TV look-ahead for the day or week, would have to include:
Bullitt
Cool Hand Luke
Unforgiven
Pale Rider
A Streetcar Named Desire
Raising Arizona
The few DVD’s I own that I’ve watched a second (or more) time include:
The Godfather
The Godfather Part II
Heat
Blade Runner
Sharky’s Machine
We probably have over 200 movies on VHS, and I suspect we’ve only gone back to watch maybe a dozen or so.
Very rarely. I watch a couple hundred movies a year an I’d guess that fewer than 10 are a repeat viewing.
Pretty much only if I’m drunk/stoned :
Willy Wonka
Star Wars (the first one)
Fast Times at Ridgemont High
The Blues Brothers
Animal House
Caddyshack
Jaws
Goodfellas
Forrest Gump
Wizard of Oz
Movies I watch more than once fall into two categories. Now, sometimes, the first category of movies will be watched in the second manner, especially since all but one are on cable quite a bit.
I will purposely re-watch these :
*The Godfather[/I (1 & 2)
Trainspotting
Notorious - That would be the Hitchcock one not the rap one 
In Bruges
BBCs Colin Firth in white shirt Pride & Prejudice
I will get drawn into these if they are on:
Lonesome Dove- any of the sequels/prequels too
Star Wars (not the prequels though)
Pulp Fiction
Kill Bill 1 & 2
Any Jane Austen flick and I’d include Bridget Jones & Clueless in this
Any version of Jane Eyre
Any Brat Pack type John Hughes movie
Oh heck yeah, I rewatch stuff all the time and often with the really good ones even though I paid close attention throughout I’ll still notice things or pick up on stuff I misesd before.
Lock, Stock and Two Smoking Barrels
Pulp Fiction
Jeremiah Johnson
Fandango
2001: ASO
Heat
The Good, the Bad and the Ugly
The Outlaw Josey Wales
Mr Mayestyk
Bullitt
Predator
Blazing Saddles
Monty Python and the Holy Grail
The Longest Day
The Conversation
Jaws
Cool Hand Luke
The Big Lebowski
Raiders of the Lost Ark
Citizen Kane
Scarface
Lethal Weapon
Body Heat
Saving Private Ryan
A Man For All Seasons
North By Northwest
Psycho
True Romance
The Searchers
Reservoir Dogs… it’s all good!
“Oh, Rowsdower.”
“Seven years after the credits?”
OMG, loved that MST3K! Wow.
Yes, I rewatch movies I like. Not as much as I used to but I do. Sometimes I do other things (email, surf the net) when it’s on but watch a big scene or two. Other times, I can get caught back up in it (Avengers, Matrix, Iron Man, Hulk, Serenity, Tucker and Dale vs Evil, Star Wars, Star Trek, Fifth Element, Sherlock Holmes, etc.) that I sit and watch it. It just varies.
And I have also done the watch it twice. I used to rent (VHS) movies as a teenager on Friday night (geek with no Friday night life) and watch them that night and then the next day before I took it back.
I would consider movies a hobby, if that’s possible, so have done most of what people said here with my my own favorites.
vislor
Frequently. Mostly it is older, B-type movies. The newer, bigger budget stuff I usually view once and most of the time that is enough.
Constantly. The theater record is held by Star Wars. I saw that one 26 times when it was first released. The all-time leader is probably Casablanca.
Yes, I watch my favorites over and over. Are we counting Rocky Horror> Because I have seen it well over 100 times; I stopped counting at 100, but it has to be close to 150.
In second place: A Knight’s Tale. Distant 3rd: LOTR trilogy.
Also rans: Jurassic Park trilogy, original Star Wars trilogy, All of Me, and many more.
Yeah, I saw Star Wars 19 times that I counted when it first came out, and I know I see the reworked version once, so that’s at least 20 times. Casablanca, no idea but it’s up there somewhere.
Ah yes, Rocky Horror. I’d estimate I saw that about a gazillion times back in the day.
Actually this is one of my criteria of a really good movie.
“Would I be willing to sit down and watch it again?”
For some, movies the answer is “Yes, I would sit down right now and watch it again.” Other movies it’s “Yes, I’d watch it again in a week or two.”
You get the idea. So yes, there are quite a few movies I’ve watched multiple times.