It's easy to  understand why  Ang Lee's 1999 film Ride With the Devil flew under the radar,  almost completely unnoticed, during its original brief theatrical  release.   It is an unusual film, one in which good and evil are intertwined in  an uncomfortably gray braid of striated allegiances.  Delicately  shaded performances (particularly by Jeffrey Wright) ground the  propulsive,  suspenseful narrative amid a brutal but realistic world. 
German-born Jacob Roedel (Tobey  Maguire) is a Missouri youth shocked into defense of the South when  his neighbor Jack Bull Chiles' (Skeet Ulrich) farm is burned and father  killed by a band of jayhawkers - militant irregular pro-Union  guerrillas.   Jake and Jack Bull join a band of bushwhackers - the pro-Confederacy  counterparts to the jayhawkers.  They join in league with George  Clyde (Simon Baker) and Clyde's best friend, a freed slave named Holt  (Jeffrey Wright).  After a series of raids under the command of  Black John Ambrose (James Caviezel), the smaller group retreats to a  rural dugout to wait out the winter. 
There, Jack Bull romances their  local sponsor's widowed daughter-in-law, Sue Lee (Jewel Kilcher).   But the relationship is short-lived; after Jack Bull dies, Roedel and  Holt team up again with Ambrose's bushwhackers for increasingly vicious  attacks.  After a murderous raid at Lawrence, Kansas, Roedel and  Holt are both wounded, and from there they escape to a safe farm where  Sue Lee has been living since Jack Bull's death.  At the farm,  Roedel and Holt recover from their wounds and make momentous decisions  about the future direction of their lives. 
No plot summary, however, can  do justice to the film's finely-woven themes.  German-born Roedel  and former slave Holt come to understand each other thanks to similar  experiences with prejudice - and, even more importantly, their muddled  sense of identity.  Roedel's family, as German immigrants, are  fully aligned with the Union - yet Roedel himself becomes a bushwhacker  out of loyalty to Jack Bull and because he has considered himself,  naturally,  a Missourian.  Later, he learns that his father has been murdered  by another band of bushwhackers, throwing his already precarious sense  of identity and political position into chaos. 
Holt, meanwhile, is a former  slave, who nevertheless finds himself fighting on the side of the  Confederacy,  like Roedel, due to personal loyalty to a friend.  Holt has no  illusions about the contradiction inherent in what he is doing; it's  his own morality that drives him to stand by Clyde.  But after  Clyde dies, Holt knows, for the first time, what real freedom feels  like. 
The intertwined stories of  Roedel and Holt elegantly transcend issues of race, just as the  characters  themselves grow to understand that there are vastly more fundamental  questions of the human condition than the color of one's skin.   At the same time, the film hardly pretends that race isn't a key issue  in American life - the struggles of the past are explicitly related  to problems that still exist in our country.  All of this is expressed  by screenwriter James Schamus and director Ang Lee with a far finer  sensibility than I am able to convey through words alone here.   Such deep conveyance of a complex and insidious social issue is rare  in film.  It's not just the way Ride With the Devil "addresses"  race; it's the way the story portrays the deeper consequences of racial  division upon individual human beings. 
Ride With the Devil  received a lot of flack for its casting, but I can't find any fault  with it.  Tobey Maguire has a tendency to come off as "soft,"  but I think he does a fine job here.  He is a good actor who carries  most of the picture without showing signs of strain.  (Although  I do take issue with the scenes of domestic comedy in the movie's  final act - Maguire handling a baby in particular - I can't blame  the actor.)  As Sue Lee, Jewel is mostly credible; the only thing  she has working against her is that she's recognizable as a music  superstar.  Otherwise, her performance is fine, if not spectacular. 
As Holt, Jeffrey Wright steals  the show.  Holt is a difficult character, as written, but Wright  brings a sense of moral clarity to Holt's words and actions.   I'll even go as far as to say that, thanks to Wright, Holt may be  one of the most complex, interesting, and significant characters from  the last couple of decades of movies. 


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