Oh, thankyouthankyouthankyou. Nobody believes me that that movie is brilliant.
I’m going to go with Very Bad Things. When I first saw it in the theatre, I couldn’t get over how fucked up it was, and wasn’t sure if I liked it. Then my friends made me go see it again. I liked it a lot more the second time.
I think so, too, but then, I’m a sucker for metafiction. 
I agree with the poster upstream that A Christmas Story didn’t grab me the first time I saw it. I remember seeing bits of it later and then thinking there were some funny things, but it doesn’t pick up until the “tongue on the flagpole” scene. Then I discovered that scene was near the beginning of the movie . . .
Bubba Ho-Tep and Being There. In both cases, I found that I appreciated the lead performances more on reflection than I did during the first viewing. I enjoyed Bruce Campbell’s Elvis more on the second viewing and Chauncy Gardner is now one of my favourite Peter Sellars characters
Die Another Day.
At first, I thought it was one of the worst James Bond movies. Now, having seen it on DVD, I tend to think of it as one of the more average, which is to say I like it.
Die Another Day is near the top of my list of James Bond movies, which I tend to dislike intensely. DAD is different in that I actually like it.
My big fat Greek wedding
My wife made take her to see it and I fell asleep during the first half hour or so.
Now I watch it every chance I get.
“Hey Ian…Were gonna kill ya!”
I didn’t like The Royal Tannenbaums when I saw it during its theatrical run, but I ended up watching it a second time because my roommate had the DVD. I thought it was great the second time.
Fellowship of the Ring.
Fell asleep through it in the theatre, tried watching it two times after that and still hated it, and finally got through it a fourth time when I was housesitting and had nothing better to do.
I liked it enough that I immediately went out and bought the other two on DVD just so I could finish watching the trilogy.
Lars von Trier’s **The Kingdom ** I thoroughly hated this movie all the way through. And three quarters of me still hates it, but I have to admit it’s unforgettable.
Intolerable Cruelty - Eh/Blah the first time through, charming the second time through, loved it the third time through. Same goes for the Big Lebowski.
Gus Van Sant’s Elephant. This is all about atmosphere, so if you don’t realize that it can feel like a pointless movie. But when you do realize that, you find it really captures like no other movie how people in the same circumstances are breathing and living in different atmospheres.
Another vote for Dr Strangelove. The first time I saw it I was probably fifteen or sixteen. I was watching it with my older brother and a bunch of his friends, they were all laughing hysterically and I just didn’t get it. I watched it again a couple years later in college and thought it was brilliant.
The first time I saw Repo Man, I can’t say I didn’t enjoy it, but was too drunk and tired to figure out what the hell was going on. And I think the next two times I saw it were pretty much the same. I was finally able to appreciate it once I was able to watch it sober and alert.