Downward Angel (2001)

John Hunter takes a job as a hit man for a Mob syndicate, but his attacks of conscience, his odd dialogue about doing this for his family (he lives alone), and his continuous returning to a woman from his past suggest that there's more to him than meets the eye. Herod, the hard-nosed boss of the killing team, alternately fascinates and repels John. One night, Herod asks him to accompany Gillian, Herod's younger sister, for an evening out. The next day, John gets the word to kill her. When he refuses and instead tries to run with her and a considerable amount of Herod's assets, the stage is set for a showdown and the revelation of who's who.