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I'll be pretty surprised if more than one film breaks the top ten. I'm guessing none will, but we'll see.
Iron Man is indeed on a pretty good pace, and it should have good legs, but it hasn't faced any real competition yet, either. I think its appeal skewed just a little too heavily male to be a really huge, long-running hit. It's a roaring success, to be sure, but I think its appeal was just a tad too limited to rank among the all-time box office smashes. And I agree, I think it'll fall a bit short of $300 million. Probably $280 million or so.