Pete the Tender (1960)

Original title: Pierrot la tendresse

In this crime drama, Michel Simon is cast as Pierrot, an elderly gangster who does not fit the stereotype -- he is soft-hearted. After a petty criminal betrays his cohorts by taking off with the loot from a big robbery, he is caught and sent to jail. Now he has served his time, and Pierrot is given the task of retrieving the stolen cash. The tyro criminal tries to use a pretty young woman who has fallen in love with him as a red herring for Pierrot's investigation. Everything backfires though, and Pierrot is left considering what to do with the loot, and with the criminal who does not yet realize he loves his attractive accomplice and could have a good life with her if he opts for walking the straight and narrow.