Pennsylvania, 1956. Frank Sheeran, a war veteran of Irish origin who works as a truck driver, accidentally meets mobster Russell Bufalino. Once Frank becomes his trusted man, Bufalino sends him to Chicago with the task of helping Jimmy Hoffa, a powerful union leader related to organized crime, with whom Frank will maintain a close friendship for nearly twenty years.

When a cash-strapped man learns his daughter has a brain tumor, he turns to his old Staten Island buddies to get back into their “family business.”

Rich Bradford seems like your everyday great boyfriend. He has a good job, a nice car and the perfect girlfriend, Amanda. What she doesn't know about him is that he is only after one thing. His best friend Stu from college days knows how much of a womanizer Rich really is. When the day comes that Rich thinks he is finally going to romance Amanda, he is interrupted by her gay friend David who walks in on them. The same day he is dumped by Amanda is Rich and Stu's fraternity reunion. How can Rich go alone? All of his fraternity brothers always saw him with a girl. Stu on the other hand gets a visit from an old fraternity brother he has kept in contact with over the years. Much to Stu's surprise, when the brother comes, he is now a beautiful woman, Erica. Stu brings Erica to the reunion and she catches Rich's eye. Will Rich finally get his just desserts or will he realize in time that his dream girl used to be a man?