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I cannot imagine watching a movie more than once that was so obtusely made that I couldn't understand it (usually, not even that much -- I'll bail after the first half hour, life's too short and all that), and the idea of watching it four or five times just boggles my mind.

I guess I just don't have the patience for such things... I'm glad you enjoyed it, but I think I'll pass.
Probably this one isn't for you. I read an interview where the director said he attempted to make it so that you'd be able to get about 70% upon first watching. The only reason he didn't make it clearer is because he felt like that explaining everything in an obvious manner is treating the audience like children.

The only qualification I'll add is that Primer doesn't start getting confusing until about the last 25 minutes- so you understand the basic premise and setup. It's just that he pulls several fast ones all at once which change multiple assumptions about the plot, one of which is elevating the importance of an event that is only discussed in passing (not even show) and this discussion was difficult to understand due to poor audio quality (though it was much easier to understand on the DVD).

At any rate, it certainly wasn't 70% clear to me the first go round, but definitely after the second. I'd say most of the clarity problems I had the first time around were because of the production quality- there were a few key conversations that I didn't quite understand due to background noise or other low budget problems. So I can forgive him that much at least.

But I don't mind watching a movie more than once if it is compelling enough.

As to what Tony said, none of the other movies mentioned earlier (of those that I've seen) require a second viewing. Memento (which I cannot recommend highly enough) I watched again because I wasn't quite sure about the "final reveal", but I've watched it several times now and love it more every go round. Pi I had absolutely no problem understanding, nor was it really that confusing- it did have the low budget thing going on, though even that one had a bigger budget than Primer.
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-Jeff
Rome did not create a great empire by having meetings; they did it by killing all those who opposed them.