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Ride with the Devil (I) (1999)

R  |   |  Drama, Romance, War  |  5 November 1999 (UK)
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Ratings: 6.8/10 from 10,832 users   Metascore: 69/100
Reviews: 159 user | 95 critic | 29 from

Jake Roedel and Jack Bull Chiles are friends in Missouri when the Civil War starts. Women and Blacks have few rights. Jack Bull's dad is killed by Union soldiers, so the young men join the ... See full summary »



(novel), (screenplay)
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Cast overview, first billed only:
Jeremy W. Auman ...
Guard (as Scott C. Sener)
Glenn Q. Pierce ...
Kathleen Warfel ...
Mrs. Chiles
Asa Chiles
Zan McLeod ...
Wedding Musician - Guitar
John Whelan ...
Wedding Musician - Accordion
Roger Landes ...
Wedding Musician - Mandolin
Jeffrey Dover ...
Wedding Musician - Drummer
Tyler Johnson ...
Wedding Musician - Drummer
Kelly Werts ...
Wedding Musician - Fiddle
Michael W. Nash ...
Horton Lee, Sr.
John Judd ...
Otto Roedel


Jake Roedel and Jack Bull Chiles are friends in Missouri when the Civil War starts. Women and Blacks have few rights. Jack Bull's dad is killed by Union soldiers, so the young men join the Bushwhackers, irregulars loyal to the South. One is a Black man, Daniel Holt, beholden to the man who bought his freedom. They skirmish then spend long hours hiding. Sue Lee, a young widow, brings them food. She and Jack Bull become lovers, and when he's grievously wounded, Jake escorts her south to a safe farm. The Bushwhackers, led by men set on revenge, make a raid into Kansas. At 19, Jake is ill at ease with war. As his friends die one after another, he must decide where honor lies. Written by <>

Plot Summary | Plot Synopsis


Drama | Romance | War | Western

Motion Picture Rating (MPAA)

Rated R for graphic war violence | See all certifications »

Parents Guide:





Release Date:

5 November 1999 (UK)  »

Also Known As:

Civil War  »

Filming Locations:


Box Office


$35,000,000 (estimated)

Opening Weekend:

£100,722 (UK) (5 November 1999)


SGD 9,103 (Singapore) (4 August 2000)

Company Credits

Show detailed on  »

Technical Specs


| (director's cut)


Aspect Ratio:

2.35 : 1
See  »

Did You Know?


Both Leonardo DiCaprio and Matt Damon passed on the lead role. Ultimately DiCaprio's best friend, Tobey Maguire, landed the part. See more »


Civil-war era skirts did not have even one in-seam pocket, let alone two. Fancy Chatelaines were used to hold purses and other items by the wealthier women, and the poorer classes made do with cloth pockets suspended from a strap that was pinned to the waistband. Flat surface pockets came in after the closing of the civil war. See more »


[first lines]
Title Card: On the western frontier of Missouri, the American Civil War was fought not by armies, but by neighbors. Informal gangs of local southern Bushwhackers fought a bloody and desperate guerrilla war against the occupying Union Army and pro-Union Jayhawkers.
Title Card: Allegiance to either side was dangerous. But it was more dangerous still to find oneself caught in the middle.
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User Reviews

What the Movie Meant to Me
3 July 2004 | by (Fremont, California, USA) – See all my reviews

My great-grandfather J.W. Daugherty was a very young teenager during the civil war in Missouri. While still twelve he was put to work as a mule-skinner by one of the "black-flag" bands of bushwackers around Cedar County, in southern Missouri. He later mastered the use of the six-shooter, and rode with Quantrill. He claimed to have ridden with Jesse and Frank James during and after the war, but every man of his generation made the same claim. Were all the claims true, it would probably be about fifty thousand in all who rode with the James boys.

J.W. claimed not to have been present during the burning of Lawrence, but so did everybody else. With so many thousand occupied in riding with the brothers James, it is passing strange that so few managed to be present during the actual burning of Lawrence, the single most important action of the Quantrill band.

I am, incidentally, named after Lawrence, that appellation being my first name.

J.W. claimed it was the James brothers who invented the idea of gripping the reins in their teeth while firing both revolvers, thereby availing oneself of a full twelve rounds in flight. J.W. ended up being the champion fiddler of Missouri, losing that title only when jealous rivals shut him out of the fiddling contests because he could read music.

Another great-grandfather of mine was James Quinn, a young captain of the Union calvery. This was a Missouri militia unit, but militias on the border often saw more action that regular units back east. His job was to guard the railroads from the "highway agents" who even then were perfecting the feat of robbing the trains of yankee gold sent south for payroll.

James and J.W. were supposed to have been on opposite sides during the Battle of Wilson's Creek, but it is impossible to know for sure. I have copies of Union orders for Captain James Quinn, having to do with the bandits operating in southern Missouri.

This film, RIDE WITH THE DEVIL, is one of the truly great American films, and the only one that even begins to get close to the feeling of the border wars, the bushwacking, the betrayals, and the split families. In Missouri, the Civil War was hell on earth, breaking every family apart at least once.

Toby McGuire is overwhelming in his grasp of the teenage border warrior who has known nothing else but killing, and who finally decides to make a new life in California. Jewel is astonishing as the young survivor widowed twice, but full of life and a desire to live it to the fullest.

The historical details are almost always spot on, and the faces of the men and women are disturbingly like what they must have been in those terrible days.

But finally, it is the script that is almost unbelievable in its power. Even when one or two words are wrong, the scriptwriter manages to somehow capture the mood and the rhythms of 19th-century speech in that part of the country, in all its humor and deep fatalism and courtesy--and yes, its cruelty too.

This is the first work of art that made me feel something close to what my great-grandfathers must have gone through. They left many stories and written records behind, but such autobiographies conceal as much as they reveal, especially about the violence and its traumatizing effects of the young males who experienced it.

I am grateful to the makers of this film, the script-writer, the author of the original book WOE TO LIVE ON, the actors and others who created RIDE WITH THE DEVIL and somehow managed to make it such a stunning work of art. To them I am thankful for bringing me closer to ancestors who made me what I am; and who--for better or worse--made this country what it is.

Lawrence Swaim

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