1960s movie; A heist shown two times; the first is flawless; the second is very funny; Not "Gambit"

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All I remember is that someone was on top of a roof trying to break into a place where something valuable was. I don't think you knew that the first version was the flawless version until after that version was finished. Maybe at that point, you saw something on the screen like "That's the way it was supposed to go." I think maybe Shirley MacLaine and Peter Ustinov were in it, but I can't be 
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Barry Burd

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Posted 2 months ago

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Bill Davis

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 A couple of possibles:

How to Steal a Million (1966) with Peter O'Toole and Audrey Hepburn


Topkapi (1964) with Peter Ustinov and Melina Mecouri


There are too many "Heist" movies to list here.  Perhaps you can just look at the list of Heist movies by year and one of them will strike a chord: