The Rules (For Men) (1999)

While some bright penny made a lot of money publishing a book for women about "The Rules" of wooing and winning a man, one man who can't be bothered to write such things down explains his own system for getting what he wants from the ladies in this comedy. Michael Vigilante (Robert Capelli Jr.) is a lawyer who considers sex to be a vitally important part of his well-being -- and the more sex (and the more women) he gets, the better. Vigilante shares his guiding philosophies on the fine art of convincing women to sleep with him when he isn't busy dealing with his former girlfriend (Christine Nagy), a crazy psychoanalyst (Frank Gorshin), a thick-headed prosecutor (Vincent Pastore), a love-starved judge (Nancy Siriani), and a humorless mob enforcer (Ken Del Vecchio). The Rules for Men also features Howard Stern Show regular Jackie Martling (aka "Jackie The Joke Man") as a partner of Vigilante's law firm