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Ride with the Devil

Skeet Ulrich, Tobey Maguire and Jewell in Ride with the Devil on the Dingus ProejctTHE DINGUS PROJECT
Jesse James in Film #15

A young Southern man from Missouri joins the rebel bushwackers during the Civil War. What he sees in the bloody guerilla warfare leads him to question his allegiance to the rebel cause. Yet Ang Lee’s compassionate film offers insights into the minds of young men like Jesse James, trapped in a violent world that tore the western states apart.

Ride with the Devil (1999)
Tobey Maguire, Skeet Ulrich, Jewel, Jeffrey Wright
132 minutes, Universal PIctures

This Ang Lee film isn’t exactly about Jesse James. It falls into the genre of "bushwacker" films and the independent forces of guerilla leaders like William Quantrill. But Ride with the Devil takes place in Lawrence, Kansas, site of the horrific raid often included in Jesse James films, and effectively depicts the life that the young James brothers lived and the events that influenced them. These experiences are often cited as the reason Jesse James turned to crime and his later actions are often explained away based on these events. Ride With the Devil presents this confusing world better than any film of the genre, yet implies that a man is not simply the product of his times, but also of his own moral courage.

Ride with the Devil 1999 on the Dingus ProjectTobey Maguire (best known as Spiderman) plays a German immigrant at the start of the Civil War when "bloody Kansas" was caught up in a gang war between pro-union "jayhawkers" and pro-Confederate "bushwackers". Both youthful guerilla groups were brutal and independent, pitting neighbor against neighbor. To make matters worse, they often camouflaged themselves in the uniforms of the opposing army as part of their practice of ambush-and-run.

Tobey as Jake Roedel (aka Dutchy) joins the bushwackers with his friend Jack Bull Chiles (Skeet Ulrich). These loyal "southern men" after a raid on his family. Wherever they travel, violence reigns. The film examines the lives of the para-military gang exiled in camps and dying in vividly depicted battles. In winter the bushwackers break into small groups to hide among local families, some supportive, many simply fearful of what might today be called "terrorists." Jack and Dutchy and a freed black named Holt (Jeffrey Wright) quarter for the winter in an earthbound hut. Their food is delivered by a young local woman Sue Lee Shelley (Jewell) who falls in love with Jack Bull. Reading a packet of stolen Union mail, Jack and Holt begin to question the cause they are fighting for.

The fight begins again when Unionist torch a local home. Jack Bull is seriously wounded in the firefight. The group is forced to amputate Jack’s arm, but are unable to save him. Holt and Dutchy return to the bushwacker camp where raiders play poker with the scalps of Dutch and Black victims. "Like dogs driven into the woods" the bushwackers are weary and angry. They plan a raid on Lawrence, Kansas in retaliation for a jail that collapsed on Confederate sympathizers there. The raiders swoop into town with a death list of Unionist families, slaughter the men and pile the corpses in the street.


The actual raid on August 21, 1863 included Frank James and Cole Younger. Ordered to kill every man and boy old enough to carry a gun, Quantrill’s raiders left 150 dead and looted and burned the city. Four days later the Union army issued "General Order Number 11", a military command that forced almost every citizen in the nearby Missouri counties to leave their homes. By driving most of the border population out of their houses, the Union army leaders hoped to stop them from hiding and helping the guerilla bands. Residents, including the James family with young Jesse (who was not part of the Lawrence raid) saw this as just one more evidence of Unionist repression.

James Schamus, who adapted the screenplay from the novel Woe to Live On by Daniel Woodrell, described the Missouri-Kansas border as "a kind of American Bosnia, with friends and neighbors fighting each other." The flamboyant bushwackers, he says, wore brightly colored hand-sewn outfits and carried six or seven pistols at a time.

What Schamus describes as a sort of "un-Western" also works as an "anti-Jesse James" film. Although he experiences the same gang lifestyle and violence as did the young Jesse James, Jake Roedel makes very different decisions about his life after the Civil War. Like most former bushwakers, he reverts to the farm life he knew earlier, melting back into history, rather than turning to crime. Dutchy marries Sue Lee, whose one encounter with Jack Bull has produced a baby. They set off with Holt to find their futures. Having discovered a sense of freedom, Holt heads off into the sunset toward Texas to find his enslaved mother while the young couple moves West as Jewell sings out the credits.

Unlike Jesse James, Dutchy comes from a solid family background. His father disapproves of his bushwacker lifestyle, while mother Zerelda James was fiercely anti-Union and pro-slavery and supported her sons guerilla activities. Dutchy too is discriminated against as an immigrant and an outsider among his comrades in arms. In the battle of Lawrence, Kansas, he is wounded, not by the enemy, but by the "friendly fire" of one of his own comrades. He sees that their prejudices are all consuming. They are, fundamentally, white supremacists, whose reign is coming to an end. By fighting alongside Daniel Holt, Dutchy sees that they are more similar than different. Jesse James, whose family owned and sold enslaved Africans, never came to this conclusion.

Of course, Dutchy is a fictional character created in the late 20th century. He comes to accept the equality of his wife, blacks, immigrants and people of different creeds. He can distinguish between right and wrong, even in the midst of a confusing war in which he himself has killed 15 men. Unlike Jesse James, he is able to accept the changes going on around him, and to pick up the pieces and move on.

Copyright © J. Dennis Robinson at All rights reserved.


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