Charlie Bartlett (2007)

Wealthy teenager Charlie Bartlett is failing miserably at fitting in at a new public high school run by the world-weary Principal Gardner. As he begins to better understand the social hierarchy, Charlie's honest charm and likability positions him as the resident "psychiatrist" dishing out advice, and the occasional prescription with his partner and fellow student, Murphy Bivens, to other students in need. Along the way, he decides to take some of his own advice, find romance, and learn to accept who he is, thus wielding a witty dark comedy about the angst-filled years before college. [imdb]