For me, it was Lost in Translation. When I watched it, it kept me interested, but I wasn’t sure I truly liked it. It was only in the days ahead that I realized something in it stayed with me. Then I started wanting to watch it again. When I saw it at CostCo last week, I bought it. I still haven’t watched it again, but that’s because I’ve had some new movies to watch.
Pulp Fiction
For some reason I absolutely hated it the first time, but ended up loving it. Weird.
Pulp Fiction
Zoolander
I’m sure there are others…
I know I’ll be branded un-cool, but at first I didn’t like Donnie Darko. Something about it pissed me off, maybe the pretentiousness of the “art house” story line. But now I kinda like it, and even though I don’t understand the cult following it has built, I would definitely recommend it as a must-see.
2001: A Space Odyssey - I saw this as a kid and thought it was pretty dull for an SF movie: too much waltz music and weird stuff and nothing happening. Many years later, I read an “explanation” of the movie, that Kubrick was making the point that any alien life would likely be so totally other as to be incomprehensible to us. I decided it was a brilliant movie. I now believe that there is more than one “explanation” for the movie, but that’s part of what makes it so great. (And how about that shot of the space station where the camera viewpoint moves through the ring?!! Done totally without the aid of computer animation - decades ahead of its time.)
I love a movie that grows on me like this. (And it doesn’t always take years…) Have to see if I can think of others.
The Fatal Glass of Beer. When I first saw it, I was very disappointed. I had expected more from W.C. Fields other than two good lines ("'Taint a fit night out for man nor beast." and “I think I’ll go out and milk the elk.”)
Then I saw it again. It seemed funnier. The snow on the hat. The giant loaf of bread. The deliberately flat acting (and singing).
By the third time, I started to get it. “You won’t consider me rude if I play with my mitts on, will ya?” “He was mighty good with mustard.”
Now, I think it’s one of the best comedy short subjects ever made. “He’s crazy.”
“Don’t forget to open the window a bit, Chester.”
Blade Runner. I was really really really disappointed in this movie the first time I saw it. There are several reasons for this:
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I was a huge Harrison Ford fan and Ridley Scott fan, so I had absurdly high expectations.
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I had just seen The Road Warrior. Really. I mean right after Road Warrior ended I walked across the street to the theater showing Blade Runner. The movies are heavily contrasted. I was still on a high from the fun and brightness of Road Warrior and not really in the right frame of mind for the more dark and cerebral Blade Runner.
The thing that sticks out most for me that I disliked in Blade Runner on initial viewing was the narration.
Later, some people who’s opinions on movies I highly respected, and who were also big fans of Ford and Scott, kept raving about how much they loved it. They had seen it several times, and were constantly quoting lines from the movie. So, I decided to try it again, and found I liked it much better. It is now one of my all-time favorites (especially the director’s cut without the narration!)!
Time bandits and Joe vs the Volcano are two movies that pop into my mind. Both movies I did not like the first time I saw them but grew to really like later.
Signs could be a more recent one. Saw it again recently (too lazy to find the remote) and enjoyed it much more than when I first saw it.
12 Monkeys- Like most of Terry Gilliam’s stuff, you really have to be in the right mood to watch it. Now that I’ve figured that out, I like this movie(and Baron Munchausen and Brazil) a lot more.
From Dusk Til Dawn. Oh, but how I hated this movie. Then I watched it a second time, out of some sick fascination I guess, and it’s really grown on me. I’m sure Salma Hayek’s dance scene in the bar has nothing to do with it. Nothing at all. Oh, and as always, Tarantino is one sick f***. God, I love that man.
Chasing Amy. I really didn’t care for it because I’m a happy endings junkie, but the story is just SO DAMN GOOD.
Masterpieces I did not like my first time through:
Barry Lyndon
Blowup
Night of the Hunter
Showgirls
Monsieur Verdoux***
Please God, nobody get him started on Showgirls. 
Well, it’s an obvious one, but the first time I rented “Citizen Kane” I thought “WTF? this is one long, boring slough about a really sleazy, unlikeable SOB.” (aside: I knew the “surprise ending” about Rosebud ahead of time.) Several years later, I saw it as part of a course on the evolution of film-making and had it’s nuances pointed out to me. Now I realize it is brilliant.
The first time I saw it, I was at a friend’s house but walked in about fifteen minutes late and was there for the beer more than I was the movie so I wound up hating it. The second time I watched it, three months ago, I was at some differen’t friends’ house and while I think I might have had a beer during that showing, my mind was focused entirely on the movie.
Was very good once I gave it a chance.
Blade Runner, of course.
When I first saw the film in the theatre I came out and was puzzled. What had I just seen? It was packed with so much cerebral matter it was difficult to process. And it was way ahead of its time. Not that I didn’t like it, I didn’t understand it. It had a tremendous, haunting impact on me. I could hardly wait till they invented BetaMax!
My betamax copy died long ago. I still have viable VHS copies of the original and the directors cut, and a DVD or two of the director’s cut.
I love it. It is my all-around most favorite film.
I can’t wait for the sequal!
A Christmas Story.
I don’t usually go for nostalgic tales. I had caught bits and pieces here and there. When I finally watched the whole thing, I really enjoyed it.
It’s “fra-gee-lee”.
28 Days Later. I liked it when I saw it but I’d felt a bit let down. Then a few weeks later I saw a program (I forget what channel) called “Anatomy of a Scene.” It examined the sequence of the lead man walking around the empty city, into the church, and ending with the gas station exploding. Once I saw all the creative research and work that had gone into it I had a tremendous appreciation for the whole thing and liked the movie more.
“Taint a fit night out (pause) for maaaaaan nor beast”.
I use that line a lot.
Nice call on a pretty obscure film. I remember seeing it my first week of college, at a freshman welcome kind of event.
I’ll go with lissener on Barry Lyndon.
Sullivan’s Travels
Almost Famous (Theatrical cut sucks, Director’s Cut is pretty good)
Intolerance
Adam’s Rib
All Quiet On The Western Front
The Birds
McCabe & Mrs. Miller
For me, it was Dark City. I fell asleep one-third of the way through it the first time - nothing was happening, Kiefer Sutherland was overacting, and all the scenes were, well, so bloody dark.
Then I saw it again at a friend’s place, and was mesmerized by it.
Maybe on some subconscious level, we realize these movies are actually decent - that’s why we seek them out for a second viewing.