The Mysteries of Pittsburgh (2008)

Pittsburgh, coming of age in the 1980s. At the beginning of June, Art Beckstein calls this the last summer of his life - after which he'll work as a stock broker. Art's father is the city's mob boss, steering Art's life, judging his choices. At a party, Art sees Jane, smart, blond, lovely. They meet; she has a boyfriend. The next day, Cleveland, the boyfriend, pulls Art from work and the summer of adventures begins. Cleveland lives close to the edge; he's explosive, with hints of problems with local thugs. The triangle of friendship gets complicated when Cleveland disappears for a couple weeks. Can Art sort out his feelings as well as help Cleveland? Where does his father fit in this?