In this hard-hitting offering from a career-besting Clint Eastwood, Penn managed to pull off an absolute head turner with this portrayal of a Boston father dealing with the brutal murder of his daughter. Tracing the blood and grit coursing through Dennis LeHane's source material novel, Penn's Jimmy Markum is a wounded shark, prowling around his old neighbourhood stomping grounds looking for answers. The real skill here was Penns ability to bring the murk from Markum's past bubbling right to the surface, as the character's desire for hood retribution leads him to make an agonisingly off the mark decision. This culminates in the film's standout scene between Markum and his old pal Dave, played by an equally mesmerising Tim Robbins. Receiving numerous plaudits across the board for his part in this superb drama, Penn's efforts were capped at the 76th Academy Awards when he rightly took home Best Actor.