REVIEW: Ride with the Devil (1999)

A film directed by Ang Lee

In my ignorant youth I largely ignored this movie, despite my love of history, because I assumed it was “just a western”, and I am largely not a huge fan of Westerns (though comics have melted that nowadays). That is an overall problem I have that I am trying to move past – me making snap judgements about things that I end up loving once I give them a fair chance. When I later took a number of history classes in college, I was shown a clip of the sacking of Lawrence, Kansas from the film and was like “I need to watch this!” Here it is, ten years or so later and i am just now getting to see this film, egged on by my recent kick on local Missouri Civil War history. I also plan to read the book at some point in the near future. Was the wait worth it?

“Ride With The Devil follows four people who are fighting for truth and justice amidst the turmoil of the American Civil War. Director Ang Lee takes us to a no man’s land on the Missouri/Kansas border where a staunch loyalist (Skeet Ulrich), an immigrant’s son (Tobey Maguire), a freed slave (Jeffrey Wright) and a young widow (Jewel) form an unlikely friendship as they learn how to survive in an uncertain time, in a place without rules and redefine the meaning of bravery and honor.”

Short answer – yes, this is a great film. Who would have thought that Ang Lee would dive into the sadly underappreciated history of the beginnings of the Civil War in Kansas and Missouri for one of his films. Adapted from the novel, Woe to Live on by Daniel Woodrell, its a fictionalized account of a small band of youthful teenagers yanked into the jaws of war and forced to understand the meaning of their lives and how they plan to live them. While this isn’t a huge action movie, there are some quite exhilarating scenes that truly show the horrors of war, no matter how small the skirmish. If you are looking for something like Gettysburg, this isn’t your film. For better or for worse, Ang Lee is known for rich character building and dramatic set pieces, and that is definitely here in spades.

Historically, there isn’t too much that is wholly inaccurate in the film (at least from what I know, I’m far from an expert). The only real issues arise when you take into account omission of some of the background leading up to the events depicted in the film and aftermath. You do see the main characters of Jake Roedel and Jack Bull Chiles join a small band of Bushwhackers after Kansas anti-slavery Jayhawkers burn Jack Bull’s home and kill his father. By seeing this, we know of Jayhawker attacks, but it isn’t dwelled on too much. You don’t really get a sense of the decade long tit-for-tat bloodbath that was plaguing the area. Neither man is ready for the problems they have got themselves into, and come to terms with very real issues including anti-immigrant sentiment (Jake is German, and Germans were staunchly Union sympathizers in Missouri), Racism towards a Frredman named Daniel Holt in the company, and the sadness watching innocent people get attacked because of their perceived allegiances.

Taking place largely in what I suspect is late 1862-1863 and ending when Quantrill rode to Texas a few months shy of 1864, This tells the story of the Bushwhacker irregular armies in their most prominent time. In many ways, showing the massive two state manhunt and General Order no. 11, a Federal order that depopulated the entirety of the western edges of Missouri as a reaction to the Lawrence Massacre, would have been a more cohesive film, but I’m no filmmaker and a historical documentary was not Ang Lee’s choice. This is hinted at in the background in a scene where Jake finds out that most of the Bushwhackers are starting to disappear or be killed. Things like this, sadly take a backseat to the romance in the film, similar in how Michael Bay’s Pearl Harbor, or even Braveheart did.

The film also goes to great pains to paint this small band of Bushwhackers as heroes. Jake is nearly a pacifist at times despite belonging to a guerilla fighting force, and their band just happens to have a slave in their ranks. While not inaccurate, as their were black Bushwhackers (Quantrill’s Scout John Noland for example), it seems somewhat like there was a deliberate effort to make you root for the underdogs no matter what horrible stuff they are up to. While it’s a noble intention to paint both sides as the same, since there were regular folks caught up in the fighting that made tough decisions to protect their families and livelihoods, the film risks tilting towards the dreaded Lost Cause idea that The Union were the de facto villains of the whole Civil War and it wasn’t actually about things such as slavery.

That isn’t to say that ALL Bushwhackers are “good guys” in the movie, The Lawrence Massacre is shown in all it’s horrors, but our ragtag band sit it out while everyone else commits atrocities. While I’ll definitely say that not all Confederates were evil, like some people that get the Good vs Bad vibe from a high school understanding of the Civil War, I am hard pressed to support pretty much anything any of the irregular volunteer armies did during Bleeding Kansas or the war itself, they were kind of bad people masquerading as defenders of their states.

Despite what I would have liked the film to go into, it stands on its own as a solid film that deserves all of the accolades it has collected. I mentioned Pearl Harbor earlier, a film that was so bogged down with melodramatic dialogue that it was a mess with a cool action scene at the end. Ride with the Devil is nothing like this, despite the focus being on romance and character-building, the dialogue is great and it never drags. If you have never seen this film, don’t be like 20 year old me, and ignore it because a cowboy hat may have been in the trailer, it’s good that such an overlooked chapter in the Civil War got an entire film made about it. If, like me, you are into Missouri history it’s a must watch.

This review is part of my 2021 series History Boy Summer, which you can read more of following this LINK. The film is currently free on Tubi, a free streaming channel.

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