Ride with the Devil (1999)

Once again, Ang Lee's versatility is stunning. Here he takes on the American Civil War by focusing on a rag tag group of Confederates in Missouri. The state doesn't have a formal militia, so they are formed ad hoc to defend the South's principles and autonomy.

Jake, a "duchy" or German immigrant's son, is as young and innocent as they come. He joins with a rich man's son, another friend and a freed slave. Together they patriotically join various groups and experience great personal loss. The group changes over time and ultimately includes a fair maiden. The transformation among these Americans is tremendous to behold and Jake is a character that will blow you away by his modest resolve (a very able and long haired Tobey Maguire).

Top marks for this one.

IMDB