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The Criminal
The Criminal is a Joseph Lozy movie with a guy named Stanley Baker. It's essentially about a petty criminal or a criminal in London who pulls a racetrack robbery and winds up accidentally or unwittingly stealing the money of a rival mob boss. The subgenre was pretty active in the 50s and 60s, but I don't think that it yet had the kind of like winking charm and sense of humor that Michael Caine brings to these movies.