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This is a "good" film I saw at the Music Box Theater in Chicago, an historical theater that shows classics and "midnight movies."

It was a French film I believe. Some men were going to rob a safe. They were drilling through a floor above the safe room and at one point used an umbrella. They used the umbrella by putting it through the hole in the floor and then opening up the umbrella to catch debris as they enlarged the hole in the floor.

Also, toward the end, and as I remember it, one of the men had decided not to be part of the heist and had an incredible run of good luck gambling at a casino. I believe that the men robbing the safe got caught. I might have these plot points a little wrong and I hope I'm not combining the memories of two movies.

Hope to get a solution from someone.

EDIT: SOLVED: I might be combining the ending of another film with this one. But I just found that the French film with the umbrella is the acclaimed classic RIFIFI.

HOWEVER I think that the casino ending is from another film. If anyone knows what this one is, I'd appreciate it.

Your second movie is almost certainly BOB LE FLAMBEUR (Bob the Gambler).  Read the Wikipedia plot summary (http://en.wikipedia.org/wiki/Bob_le_flambeur#Synopsis).  It would be very easy to confuse these two French caper movies that came out within a year of one another.