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Of all the legacies parents seek to pass on to their children -- a moral compass, an intellectual curiosity -- none elicits more gratification than the the family business. But what if the profession isn't nursing or teaching or cooking? What if the trade in question is crime?
Some movies (The Road to Perdition) find the parent in conflict with passing on such a skill but others entertainingly do not. These latter films find the parent cultivating, not curbing, the child's mercenary instincts. Think of The Grifters. Lilly Dillon (Angelica Huston) is devoted to her son (John Cusack), a fellow con artist. That she ends up more greedy than nurturing doesn't mean that she hadn't hoped that her son would turn out to be a master swindler.
A little more ethical is the father-daughter duo in Paper Moon -- played by the real life father-daughter duo of Ryan and Tatum O'Neal. They work smoothly as a pair of crooks, but the dad does give occasional lip service about how maybe this isn't the best may to make a living.
In Matchstick Men, the seriously neurotic con (Nicolas Cage) is initially reluctant to see his daughter (Alison Lohman) join forces with him but he's undone by her flattery. "You're a con man?" she asks, slightly awestruck. "Con artist, flim flam man, matchstick man, loser, whatever you want to call it, take your pick," he replies. You can almost hear his reluctant satisfaction that his daughter finds his work... interesting.
Such joys are shortlived as these things so seldom end well. See for yourself.