The Last Castle, 2001 —
In addition to being reunited with his Get Shorty comrade, Delroy Lindo, James Gandolfini got to go one-on-one with the great one, Robert Redford in this military drama film. Playing Colonel Winter, Gandolfini serves as a military prison's commandant whose admiration of Redford's Lieutenant General Eugene Irwin spurns a revolt on the yard.
Gandolfini's most gangsterfied moment comes when he uses his prison military force to attack Irwin's renegades and create calamity within the "castle" he is said to be the king of.
Watch the trailer below: