Mad Dog and Glory

Mad Dog and Glory is a 1993 American crime comedydrama film directed by John McNaughton and starring Robert De Niro, Uma Thurman, and Bill Murray.

Mad Dog learns that Glory is trying to pay off a personal debt and wants nothing to do with Milo beyond that. After an awkward start, they fall in love. Mad Dog wants her to move into his apartment, but Milo has no intention of losing Glory permanently. Milo says that Mad Dog has to pay 40,000 to give Glory her freedom, and sends one of his thugs to back up this threat. Mad Dogs partner, Mike Caruso, fights the thug on Mad Dogs behalf.Mad Dog does his best to get the money but falls short by 12,500. Knowing that Mike can no longer fight his battles, he works up the courage to fight for Glory himself, and ends up fighting with Milo in the street. Fed up, Milo washes his hands of Mad Dog and lets Glory go with no strings attached. ........

Source: Wikipedia