What Is Ride with the Devil About?
The premise of Ride with the Devil in 332 words, with nothing given away. The full story follows below.
In the smoky hills of Missouri, the American Civil War looms not just as a clash of armies but as a constant, ragged heartbeat that rattles every homestead and road. The landscape is a patchwork of farms, hidden digouts, and restless towns where loyalty is as fluid as the mist that rolls over the rivers. Amid this volatile frontier, the film captures a gritty, relentless atmosphere where survival and ideology collide, painting a portrait of a region caught in the throes of a conflict that is as personal as it is political.
Jake Roedel and Jack Chiles are two inseparable friends whose lives become entwined with the war’s chaotic rhythm. Jake, the son of a German immigrant, carries the weight of cultural suspicion, while Jack, raised on a prosperous planter estate, watches his world crumble under the fire of guerrilla warfare. United by a fierce bond and a shared sense of purpose, they navigate the shadowy line between outlaw and defender, their camaraderie offering both a shield and a compass in a world where the distinction between right and wrong blurs with each new raid.
When the duo takes shelter with a grieving war widow, the fragile peace of the homestead gives rise to a subtle, hopeful romance. Sue Lee Shelley Evans embodies the lingering tenderness that persists amid ruin, and her presence awakens in Jake an unfamiliar yearning for something beyond the perpetual cycle of violence. The close‑knit group they form—with former slaves, fellow fighters, and reluctant allies—creates a temporary family that steadies them against the surrounding chaos.
As the war intensifies, Jake finds himself poised on the edge of a decisive crossroads. The promise of redemption beckons, yet the path is littered with dangerous political currents and the looming specter of vengeance. The film sustains a tense, brooding tone, inviting viewers to wonder how far a young man will go to protect his friends, honor his convictions, and perhaps, discover a sliver of hope in the midst of unrelenting turmoil.
What Happens in Ride with the Devil?
The complete story of Ride with the Devil, from the first scene to the last, in 764 words (about 3 minutes). Spoilers throughout. Names in the text link to 1 cast member page.
Spoilers ahead
Jake Roedel and Jack Bull Chiles are inseparable friends from Lexington, Missouri, facing the tumultuous onset of the Civil War in April 1861. Jack hails from a prosperous planter family, while Jake is the son of a German immigrant who cautions him about the rising anti-German sentiment among Southerners. Tragedy strikes when Jayhawkers torch the Chiles’ plantation and execute Jack’s father, prompting Jack to flee with Jake.
As a year passes, the duo aligns with the First Missouri Irregulars under the command of Black John Ambrose, a makeshift unit pledged to the Confederate cause in Missouri. They fight alongside George Clyde, former slave Holt, and the cruel Pitt Mackeson, who harbors a deep-seated hatred for the literate Jake. These Irregulars engage in guerrilla warfare against the Jayhawkers, with backing from pro-Confederate locals. In a heartbreaking turn, Jake chooses to spare Unionist Alf Bowden, a former neighbor, only to learn later that Alf has avenged himself by killing Jake’s father.
To evade the winter’s chill, Jake, Jack, Holt, and Clyde retreat to a dugout on the Evans family property. It is here that romance blossoms between Jack and the young widow Sue Lee Shelley Evans. Meanwhile, Clyde pursues a relationship with Juanita Willard. Jake finds companionship with Holt as they sift through captured letters, which leads Holt, revealing his true name is Daniel, to express gratitude towards Clyde for purchasing his freedom. Their lives take a devastating turn when a Jayhawker attack results in the destruction of the Evans family home, leaving the patriarch dead and Jack critically injured. In a moment of betrayal, Clyde abandons them under the pretense of seeking medical assistance, rejoining the Irregulars and Captain Purdees. Jake and Holt make a desperate attempt to save Jack’s life by amputating his arm, but Jack succumbs to gangrene complications.
In a bid to find solace, Jake and Holt escort Sue Lee to the Brown family’s homestead before setting out to locate Clyde and the Irregulars. They are met with grim news that Union forces have been pursuing and decimating many of their comrades. Joining forces with guerrillas led by William Quantrill, the men prepare for a raid on Lawrence, Kansas, on August 21, 1863. The pro-South forces efficiently overpower the small defending garrison, unleashing chaos as they burn and loot the town, indiscriminately killing Union supporters and black freedmen. Choosing to avoid the carnage, Jake and Holt seek refuge by eating breakfast at a nearby restaurant, only to find themselves threatened by Mackeson, whom they force to retreat at gunpoint.
As the guerrillas make their escape, Ambrose confronts Jake, accusing him of abandoning his Southern loyalties, while Union troops relentlessly pursue them into the wilderness. In a gripping scene, Quantrill and Ambrose command their men to feign retreat and form a defensive stance against their pursuers. Mackeson fires upon Jake, and Holt is struck while trying to defend him. In a tragic turn, Clyde rushes to Holt’s aid but is mortally wounded in the process. As they flee the chaos with fellow comrade Cave Wyatt, they seek refuge with the Brown family. Meanwhile, Sue Lee gives birth to Jack’s daughter, Grace Shelley Chiles, leading Cave to urge Jake to marry her, presuming him to be the child’s father.
With both Jack and Clyde gone, Jake and Holt contemplate their uncertain futures. Jake reveals his reluctance to rejoin the Irregulars, feeling the tide of war turning against the Confederacy. Conversely, Holt expresses a complicated sense of freedom now that his friend has passed. They are soon informed of Quantrill’s escape to Kentucky, leaving the remaining Irregulars as outlaws, including the vengeful Mackeson who seeks retribution against Jake. After their recovery, Mr. Brown introduces a minister, Reverend Horace Right, pushing a reluctant Jake toward marrying Sue Lee—a union that, with time, blossoms into genuine affection as he grows to care for her and their child.
Setting off for California with his newfound family, Jake, now 19, makes a symbolic decision to cut his hair, a commitment he had vowed to uphold until the war concluded. During their journey, Jake and Holt encounter Mackeson, who is desperately trying to evade capture alongside another surviving Irregular. Although heading to Mackeson’s Union-occupied hometown of Newport, Missouri could signal certain death, the encounter escalates when Mackeson, in a state of agitation, unwittingly prompts Jake and Holt to draw their weapons. Amidst the tension, Mackeson escapes. Ultimately, Holt parts ways with Jake, seeking to save his mother from slavery in Texas. The two friends share a heartfelt handshake and bid farewell, each pursuing their divergent paths in an uncertain world.
Ride with the Devil Timeline: Every Key Event in Order
15 key events in the order they happen, from “Beginning of the Civil War” to “Parting Ways with Holt”. 7 events name a place, across 6 locations.
- 1
Beginning of the Civil War
In April 1861, the Civil War erupts in the United States, drastically altering the lives of many, including two friends from Lexington, Missouri. Jake Roedel and Jack Bull Chiles find themselves on opposing sides of a growing conflict that will test their bond and influence their futures.
When:April 1861 Where:Lexington, Missouri
- 2
Tragic Attack on the Chiles' Plantation
The peace of the Chiles family is shattered when a group of Jayhawkers attacks their plantation, resulting in the devastating murder of Jack's father. In the wake of this tragedy, Jack and Jake make the difficult decision to flee their home and seek refuge elsewhere.
Where:Chiles' Plantation
- 3
Joining the First Missouri Irregulars
A year later, Jake and Jack conscript into the First Missouri Irregulars, a Confederate militia unit under the leadership of John Ambrose. The young men become embroiled in guerrilla warfare, fighting against the Jayhawkers and wrestling with their own moral dilemmas.
When:April 1862
- 4
Conflict Over Moral Choices
During their time with the Irregulars, Jake faces a critical choice when he spares the life of Alf Bowden, a Unionist neighbor. Unfortunately, this kindness comes back to haunt him when he discovers that Alf later avenged himself by killing Jake's father.
- 5
Life in the Evans Dugout
To escape the harsh winter, Jake, Jack, Holt, and Clyde take refuge in a dugout on the Evans family property. While these tensions brew beneath the surface, romantic relationships develop, particularly between Jack and the widow Sue Lee, adding layers of complexity to their situation.
Where:Evans Family Property
- 6
Destruction of the Evans Home
The fragile peace is shattered when a Jayhawker attack destroys the Evans family home, resulting in the death of the patriarch and leaving Jack severely injured. As the group struggles with the consequences of this violence, trust issues arise when Clyde abandons them at a critical moment.
Where:Evans Family Home
- 7
A Desperate Attempt to Save Jack
In a race against time, after being left behind by Clyde, Jake and Holt try to save Jack’s life by amputating his arm. Tragically, their efforts are in vain, and complications from gangrene lead to Jack's eventual death, deepening Jake's sense of loss and betrayal.
- 8
Joining William Quantrill
In search of answers and a way to cope with their losses, Jake and Holt align themselves with guerrillas under Captain William Quantrill. They prepare for an infamous raid on Lawrence, Kansas, setting the stage for one of the Civil War's bloodiest confrontations.
When:August 21, 1863 Where:Lawrence, Kansas
- 9
The Raid on Lawrence
The chaos that ensues during the Lawrence raid sees the pro-South forces devastate the town, killing many, including Union supporters and black freedmen. With their morals challenged, Jake and Holt manage to avoid the frenzy, choosing instead to take shelter in a nearby restaurant.
When:August 21, 1863 Where:Lawrence, Kansas
- 10
Confrontation with Mackeson
As the group escapes from Lawrence, a confrontation with the brutal Pitt Mackeson unfolds. The tension mounts as Jake and Holt find themselves facing Mackeson at gunpoint, ultimately forcing him to retreat and leaving behind unresolved animosities.
Show the other 5 events of Ride with the Devil Hide the last 5 events
- 11
Consequences of War
In the aftermath of the raid, Union troops relentlessly pursue the guerrilla fighters, leading to further conflict. Tragedy strikes again when Clyde, trying to aid Holt after he is shot, suffers a fatal injury, compounding the grief already felt by Jake.
- 12
Jack's Child is Born
In the midst of loss, a new life emerges as Sue Lee gives birth to Jack's daughter, Grace Shelley Chiles. This event renews discussions about marriage and family, pressing Jake into a reluctant role as Sue Lee’s protector amid their turbulent circumstances.
- 13
Jake's Commitment to a New Life
With Jack and Clyde gone, Jake grapples with the uncertainty of his future. After being introduced to Reverend Horace Right, he finds himself pushed towards marrying Sue Lee, ultimately leading to a relationship based on care rather than mere obligation.
- 14
Journey to California
As Jake embarks on a journey to California with his new family, he marks this new chapter in his life by cutting his hair, a personal promise made during the turmoil of war. This act symbolizes his evolution from a soldier to a family man.
Where:California
- 15
Parting Ways with Holt
At a crossroads, Jake and Holt share a poignant farewell as Holt decides to head to Texas to save his mother from slavery. The two friends leave behind a world steeped in conflict, each embarking on a new journey filled with uncertainty and hope.
Who Are the Main Characters in Ride with the Devil?
4 characters, among them Jake Roedel (Tobey Maguire), Jack Bull Chiles (Skeet Ulrich) and Holt (Character's Name Unknown): who each one is and the part they play in the story. 2 of them link to the actor’s page.
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Jake Roedel (Tobey Maguire)
Played by Tobey Maguire
Jake Roedel is a complex character caught in the turmoil of the Civil War, navigating his loyalties and personal losses. As a son of a German immigrant, he grapples with rising tensions and ultimately faces moral dilemmas in the heat of battle. His journey reflects a growth in maturity as he confronts the harsh realities of conflict and the responsibilities of newfound fatherhood.
- 🧑🤝🧑 Friendship
- 💔 Loss
- ⚖️ Morality
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Jack Bull Chiles (Skeet Ulrich)
Played by Skeet Ulrich
Jack Bull Chiles, hailing from a wealthy planter family, embodies the privilege and troubles of his background. His character experiences profound tragedy with the loss of his father, propelling him into a frantic fight for survival. Jack's bond with Jake underscores the theme of friendship amidst adversity, and his character arc illustrates the harsh impacts of war on personal ambitions and dreams.
- 🪖 Conflict
- 💔 Tragedy
- 🚶♂️ Journey
- H(
Holt (Character's Name Unknown)
Holt, a former slave, is a representation of resilience and the quest for freedom in a tumultuous time. His character evolves as he navigates changes in relationships and alliances, expressing gratitude and loyalty towards friends. Holt's journey intertwines personal sacrifice with a longing for autonomy, revealing the complexities of his identity against the backdrop of war.
- 🏹 Resilience
- 🔍 Discovery
- ✊ Freedom
- SL
Sue Lee Shelley Evans (Character's Name Unknown)
Sue Lee emerges as a pivotal character representing love and emotional strength in the narrative. As a young widow, she navigates her own grief while becoming a source of support for Jake and Jack. Her pregnancy symbolizes hope and continuity amid chaos, and her relationship with Jake gradually evolves into a partnership rooted in genuine affection.
- 💖 Love
- 👶 Family
- 🤝 Support
Where and When Is Ride with the Devil Set?
Ride with the Devil is set in Lexington, Missouri, Lawrence and Kansas (April 1861 - August 1863). Here is why the time and place matter to the story.
When
April 1861 - August 1863
The film is set during the Civil War, a pivotal time in American history characterized by fierce battles between Union and Confederate forces. This period saw the rise of guerrilla warfare, as traditional combat paradigms were disrupted, leading to horrific acts of violence and personal tragedies. The emotional turmoil and shifting loyalties of individuals navigating this chaos underscore the profound impact of war on personal lives.
Where
Lexington, Missouri, Lawrence, Kansas
The story unfolds primarily in Lexington, Missouri, a town deeply affected by the Civil War, known for its plantations and struggles amidst rising tensions. Lawrence, Kansas, becomes a significant site of conflict, representing the brutality of the war with its tragic destruction. These places reflect the tumultuous era and the complex interactions between communities during a time of division.
- 🏡 Home
- ⚔️ Battle
- 🌾 Countryside
What Are the Themes of Ride with the Devil?
3 ideas the story keeps returning to, among them War and Conflict, Love and Sacrifice and Identity and Freedom.
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01
War and Conflict
The theme of war permeates the narrative, showcasing the brutal and senseless nature of violence during the Civil War. Characters are forced to navigate their loyalties, decisions, and the repercussions of their actions amidst ongoing conflict, highlighting the personal cost of war. The film examines how friendships are tested and how individuals cope with loss in a fractured society.
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02
Love and Sacrifice
Amidst the chaos of war, themes of love and sacrifice emerge, particularly in the relationships formed and tested throughout the film. Jake's evolving affection for Sue Lee and the bonds between friends emphasize the importance of human connection in dire circumstances. As characters face loss and hardship, their sacrifices highlight the resilience of love in overcoming adversity.
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03
Identity and Freedom
The struggle for identity and the quest for freedom are central to the characters' journeys. Jake's internal conflict regarding his loyalties juxtaposes with Holt's pursuit of independence and emancipation. The film illustrates how the war compels individuals to confront their beliefs and aspirations, shaping their identities in a landscape of turmoil and uncertainty.
What Kind of Film Is Ride with the Devil?
Melancholic in tone, with variable pacing and a moderate story, going by the plot summary.
- Tone
- Melancholic
- Pacing
- Variable
- Story
- Moderate
- Intensity
- High
- Ending
- Bittersweet
A somber and brutal war drama that follows young guerrillas through the moral chaos of the Civil War, marked by tragic loss, harsh survival, and a slow, hard-won path toward personal redemption.
- somber
- brutal
- brooding
- loyal
- harsh
- reflective
- guerrilla warfare
- friendship
- revenge
- coming of age
Content notes: war violence, murder, racial brutality, civilian massacre, betrayal.
Quiz
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Where to Watch Ride with the Devil
Rent or buy it from Amazon Video and Apple TV Store. US availability and prices from JustWatch.
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