🎯 Quick Overview
Trailer
- Director: Ang Lee
- Genre: Drama, Romance, War, Western
- Release year: 1999
- Runtime (length): 2h 18min
- IMDb rating: 6.7/10 (15K votes)
- Rotten Tomatoes: 63%
😅 Plot Summary – Badly Explained
Two best friends decide to join a Confederate boy band, only to discover that their manager is evil and the group is destined for a very public, explosive breakup.
🍿 Ride with the Devil: Detailed Plot Synopsis
Setting the Stage: Missouri, 1861
Set in Missouri during the tumultuous early years of the Civil War, ‘Ride with the Devil’ introduces Jake Roedel and Jack Bull Chiles, two friends grappling with the escalating conflict. The social and political landscape is fraught with tension, especially in the border states where loyalties are divided and violence is commonplace. Their friendship is tested when Jack Bull’s father is killed by Union soldiers, setting them on a path of revenge and allegiance to the Confederacy.

Joining the Bushwhackers
Fueled by grief and a desire for retribution, Jake and Jack Bull join the Bushwhackers, a group of Confederate guerrillas engaging in irregular warfare. This band operates outside the formal structure of the Confederate army, relying on ambushes and raids against Union sympathizers. The film portrays the harsh realities of their existence, highlighting the violence and moral ambiguities of guerrilla warfare. Daniel Holt, a freed slave, also joins their ranks, adding complexity to their cause and challenging racial norms.

Survival and Moral Dilemmas
As the war progresses, the Bushwhackers face increasing hardships, including dwindling supplies, constant threat of Union patrols, and the brutal realities of their actions. Jake grapples with the moral implications of their violence, especially after witnessing the Lawrence Massacre, a particularly brutal attack on a pro-Union town. The film explores themes of loyalty, friendship, and the cost of war, as Jake begins to question the Bushwhackers’ mission and his own role in the conflict.

⚠️ Spoilers and Ending Explained
🎬 Cast & Characters
- Jake Roedel (Tobey Maguire): A young Missourian who joins the Bushwhackers, grappling with his conscience amidst the brutality of the Civil War.
- Jack Bull Chiles (Skeet Ulrich): Jake’s loyal friend who joins the Bushwhackers seeking revenge for his father’s death.
- Sue Lee Shelley (Jewel): A young widow who becomes involved with the Bushwhackers and finds herself in a complex relationship with Jake and Jack Bull.
- Daniel Holt (Jeffrey Wright): A freed slave who controversially fights alongside the Bushwhackers, searching for his place in a divided nation.
- Pitt Mackeson (Jonathan Rhys Meyers): A volatile and ruthless Bushwhacker whose actions test the moral boundaries of Jake and his comrades.
💬 Memorable Quotes
- Jack Bull Chiles: “I don’t believe I’d be too welcome in Lawrence.” – Jack Bull Chiles sarcastically declares his lack of intention of visiting the anti-confederate town of Lawrence, Kansas.
- Mr. Evans: “Before they built their church, even, they built that schoolhouse. And they let in every tailor’s son… and every farmer’s daughter in that country.” – During a discussion of the Civil War, Mr. Evans reflects on the roots of the Yankee invasion and their emphasis on education.
💰Box Office
- Budget: $38,000,000
- Domestic Gross: $635,096
- Worldwide Gross: $635,096
💥 Ride with the Devil Reviews
Personal Review
I remember seeing this in a small theater and being completely drawn into the world of these young men caught up in the Civil War. The cinematography was breathtaking, and the acting was top-notch. I really felt the emotional turmoil of Tobey Maguire’s character as he questioned his allegiances and struggled to find his place in a world torn apart by conflict. The scenes with Jewel were surprisingly tender and poignant. It made a lasting impression on me, and I still think about it today.
- Who would enjoy:
- “Fans of historical dramas set during the American Civil War.”
- “Viewers interested in stories about moral dilemmas and character development in times of conflict.”
- “Audiences who appreciate well-crafted cinematography and nuanced performances.”
- Content warnings ⚠:
- “Graphic violence and war-related gore.”
- “Mature themes including death, grief, and racial tensions.”
- “Some scenes may be disturbing for sensitive viewers.”
Professional Reviews
- The New York Times: “Ride With the Devil offers a stark and uncompromising look at a lesser-known chapter of the Civil War. Ang Lee’s direction is masterful, and the performances are uniformly strong, creating a powerful and thought-provoking cinematic experience. Although slow, the film never fails to make an impression.
- Rolling Stone: “Lee avoids easy heroism, focusing on the brutal realities of war and the complex moral landscape of the time. While the film’s pace may deter some viewers, its unflinching portrayal of violence and its exploration of loyalty make it a worthwhile watch. Jewel impresses in her debut.
Audience Reactions
The authentic costumes and language brought the Civil War era to life.: Viewers appreciated the film’s historical accuracy and attention to detail.
Jewel’s acting debut was surprisingly impressive and added depth to the story.: Many found Jewel’s performance to be a standout, exceeding expectations.
Overall Consensus: Ride With the Devil is a thought-provoking and visually stunning Civil War drama that offers a unique perspective on a turbulent period in American history. While its slow pace may not appeal to all viewers, its historical accuracy, strong performances, and complex themes make it a worthwhile watch.
Awards
🛠️ Behind the Scenes
- “Jewel, known primarily as a singer-songwriter, was cast by Ang Lee for her ‘period-appropriate’ crooked teeth.”
- “The film was shot on location in Missouri and Kansas to enhance authenticity.”
- “Ang Lee aimed for historical accuracy, employing hundreds of Civil War re-enactors and meticulously recreating period details.”
🖥️ How to Watch Ride with the Devil?
As of today, there is no specific platform streaming ‘Ride with the Devil’ as part of a subscription service. Check for availability on platforms like Prime Video, Apple TV, or Vudu where it may be available to rent or purchase. Physical copies (DVD/Blu-ray) can also be found through online retailers like Amazon.

🎥 Similar Movies
If you enjoyed Ride with the Devil, you might like these similar films:
- The Outlaw Josey Wales (1976): Shares the theme of Confederate guerilla warfare and a man seeking vengeance after the Civil War.
- Gettysburg (1993): Another Civil War drama depicting the time period, offering a broader view of the war.
- Cold Mountain (2003): Explores the personal struggles and relationships during the Civil War era.
🛒 Ride with the Devil Related Products
- The Civil War: A Film by Ken Burns: A comprehensive and critically acclaimed documentary series offering an in-depth look at the American Civil War.
- Civil War Toy Soldiers Playset – Figures of Union and Confederate Armies: A playset of toy soldiers depicting both Union and Confederate armies for imaginative play and historical reenactments.
- Civil War Era Photography Book: This photo book captures the period perfectly! It’s packed with images to help you feel and see this period.
- Confederate Flag Bandana: Celebrate the history, pride, and heritage of the Confederate South, while showing the South will rise again. Show your Southern and American Pride, or give this to the Southern Gentlemen or Ladies. Perfect for bikers, costumes, work, or decoration.
🎧 Soundtrack
Ride with the Devil features a captivating soundtrack that enhances the movie’s atmosphere and emotional impact. Here are some notable tracks:
- “Miss McLeod’s Reel” – performed by Traditional
- “O Shenandoah” – performed by Various Artists (Traditional)
You can find the complete soundtrack on Amazon Music and Apple Music.
🤨 FAQ
‘Ride with the Devil’ is based on the novel ‘Woe to Live On’ by Daniel Woodrell, which is inspired by historical events during the American Civil War, specifically the conflict between pro-Confederate Bushwhackers and pro-Union Jayhawkers in Missouri and Kansas. While the characters are fictional, the film accurately depicts the historical context and the brutal nature of the guerrilla warfare that took place.
Daniel Holt, a freed slave fighting alongside Confederate Bushwhackers, is a complex character who challenges conventional narratives about race and loyalty during the Civil War. He represents the diverse motivations of individuals caught in the conflict and raises questions about the meaning of freedom and belonging. His presence highlights the moral ambiguities of the war and the ways in which personal relationships could transcend ideological divides.
In the context of the American Civil War, ‘bushwhackers’ were Confederate guerrillas who operated independently of the regular Confederate army. They often engaged in ambushes and raids against Union troops and sympathizers, particularly in the border states like Missouri and Kansas. Their actions were often characterized by extreme violence and contributed to the overall brutality of the conflict.
🔥 Bonus Content
Tobey Maguire “Ride With The Devil” 10/24/99 – Bobbie Wygant Archive
Ever wondered what Tobey Maguire thought about playing a Civil War character? This vintage interview gives you a glimpse into his mind during the making of ‘Ride With The Devil’ – super interesting to see how he approached the role!
12 Most Historically Accurate Westerns Ever Filmed
Is ‘Ride With The Devil’ a true reflection of the Wild West or just another Hollywood fantasy? This video breaks down the most historically accurate Westerns, and trust me, their take on ‘Ride With The Devil’ is pretty insightful!
“Ride with the Devil” – Clark Farm Civil War Shootout
Want to understand the real history behind that intense shootout scene in ‘Ride With The Devil’? This video dives deep into the historical accuracy of the film, revealing some fascinating facts about the Civil War.
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