A question was posed on a recent podcast: Are there any movies you have NOT liked on initial viewing but then changed your opinion on later viewings? A couple movies came to mind. Both Napoleon Dynamite and Anchorman: The Legend of Ron Burgundy were complete misses for me on the first take. They stuck with me though and I've watched both several times since those first impressions.
But the biggest turnaround was Shutter Island, which I watched again last night. This was a movie that came packaged with the knowledge that a M. Night Shyamalan-type twist was waiting for you at the end. And when it came, it was a big "meh". The ending wasn't something that really "clicked" the rest of the movie into a different focus.
Movies that really accomplished that trick well were The Sixth Sense and The Others. Compared to those standouts, Shutter Island's reveal seemed kind of muted and lacked the impact of the other films. But watching it again and knowing the full context, the impact can be felt in the subtle and telling performances of the entire cast. A great movie on second, third, and fourth viewings.