Six Ways to Sunday (1999)

Norman Reedus stars as Harry Odum, a henpecked, 18-year-old momma's boy in Youngstown, Ohio, who -- with his violent temper -- impresses a local boss of the Jewish Mafia. Soon he's found his calling as a hit man alongside his crack addict partner Arnie Finklestein (Adrien Brody), and he discovers that his rage and complicated psychosis fuel his murderous abilities. Harry also falls for the organization's limping, Hungarian-born maid Iris (Elina Lowensohn), a romance complicated by Harry's Oedipal, sexual relationship with his domineering mother Kate (Deborah Harry).