Ricardo Cortez wears an unidentified watch

Pre-Code Hollywood let its characters get away with things that would be impossible two years later, and Midnight Mary (1933) takes full advantage. William Wellman directed Loretta Young as Mary, a woman on trial for murder who flashes back through a life that took her from poverty to the criminal underworld. Ricardo Cortez plays Leo, the gangster who pulls her in. Cortez made a career playing smooth, dangerous men in the early thirties — he was the original Sam Spade in the 1931 Maltese Falcon.

The available image is a backdrop, so Leo's watch is not visible. It has been described as a rectangular dress watch, which would be right for a well-dressed gangster in 1933. Rectangular and tonneau cases were fashionable in that era, and a man like Leo would wear something that said money without saying how he got it.