Mad Dog And Glory

Mad Dog and Glory (1993) at IMDB

This is a story about De Niro, a crime scene investigator in Chicago who has an ironic nickname "Mad Dog" when he's actually pretty timid, Bill Murray as a loan shark who was nearly killed in a holdup that De Niro walked into, and Uma Thurmond (Glory) who is paying a debt to Murray by being his slave. Murray's character decides to send Glory over to keep De Niro company for a week as a thank you, and then the predictable happens.

Worth noting is that De Niro's assistant CSI is none other than David Caruso, with no scream and no sunglasses. Caruso's character says at one point "If I ever had an intelligent thought it would die lonely."

Minor content advisory: some people think the sex scene between old man De Niro (about 60) and young woman Uma (about 23) is a "can't unsee" moment.

Final thought: thought Murray was good here, and De Niro so-so