Night and the City (1992)

Robert DeNiro and Jessica Lange are the most impossible couple. He's a failed lawyer. She's a common waitress. Together they get in a downward spiral, as they can't seem to deal with their problems. The lawyer just failed winning a case in court against a famous boxing organizer and he wants revenge by catching the organizer on his own territory: boxing. Although he knows nothing about boxing, with his fine talk he finds the help of a couple of people like the brother of his new enemy. But the relationship with his waitress doesn't make things double as hard.