Expelled from yet another private school for his blossoming, though illegal, entrepreneurial activities, wealthy teenager Charlie Bartlett (Yelchin) finds himself at a regular varsity. His geeky appearance gets him a first day beating from the school bully so his overly medicated mother (Hope Davis) calls in the family psychiatrist to help him out. An opportunity not to be missed, Charlie sets himself up as the school agony aunt, dishing out prescription drugs from the school rest rooms, courtesy of the family shrink. His charm, charisma and access to medication soon starts to win him new friends as well as the attentions of the principals daughter, much to the annoyance of the Principal (Robert Downey Jr.) a man battling his own demons.