Film i saw as a kid (like almost 20 years ago)

Howdy, the movie was about a guy that was related to a crime figure (maybe his son?) And needed to have a rite of passage ro enter said organization. So he had to choose a person on a phone list to kill. He chose a random girl and failed to kill her first time.

SPOILER:
His trainer loses patience and helps the girl kill him so she enters the organization instead.