Ride with the Devil (1999) Review: A Gritty and Nuanced Civil War Drama

Directed by Ang Lee and based on Daniel Woodrell’s novel Woe to Live On, Ride with the Devil is a unique and introspective take on the Civil War. Departing from large-scale battles, the film explores the moral ambiguities and personal struggles of guerrilla fighters during the violent conflict along the Kansas-Missouri border. Featuring an ensemble cast led by Tobey Maguire, Skeet Ulrich, and Jewel, the film is a thought-provoking and visually stunning examination of loyalty, identity, and survival.

Plot Overview: The Guerrilla War Along the Border

Set during the early 1860s, Ride with the Devil focuses on a group of Southern sympathizers, the Bushwhackers, who engage in guerrilla warfare against the Union-aligned Jayhawkers. At the heart of the story are two childhood friends:

• Jake Roedel (Tobey Maguire): A young German-American whose Southern allegiance is complicated by his outsider status.
• Jack Bull Chiles (Skeet Ulrich): A charismatic and loyal Southerner seeking revenge for his father’s murder.

As the war intensifies, Jake and Jack Bull join the Bushwhackers and navigate the brutal realities of guerrilla warfare. Along the way, they form alliances with Daniel Holt (Jeffrey Wright), a freed slave fighting for the South, and Sue Lee Shelley (Jewel), a widowed Southern woman who becomes a symbol of resilience amid the chaos.

The film culminates in the infamous Lawrence Massacre, a harrowing event that underscores the moral complexities and devastating consequences of the Civil War.

Tobey Maguire as Jake Roedel: A Quietly Complex Lead

Tobey Maguire delivers a subdued yet compelling performance as Jake Roedel, capturing the character’s inner conflict and quiet resilience. Jake’s journey from a naive young man to a disillusioned fighter is central to the film’s emotional core, and Maguire’s portrayal adds depth to the story’s exploration of loyalty and identity.

Skeet Ulrich as Jack Bull Chiles: A Charismatic Counterpoint

Skeet Ulrich brings charm and energy to the role of Jack Bull, providing a stark contrast to Maguire’s introspective Jake. Ulrich’s performance highlights Jack Bull’s loyalty and determination, making his bond with Jake one of the film’s most poignant relationships.

Jeffrey Wright as Daniel Holt: A Standout Performance

Jeffrey Wright’s portrayal of Daniel Holt is one of the film’s standout elements. As a freed slave who remains loyal to his Southern master, Holt’s character embodies the complexities of identity and allegiance during the Civil War. Wright’s nuanced performance adds emotional depth and gravitas to the story.

Jewel as Sue Lee Shelley: A Resilient and Compassionate Presence

In her acting debut, Jewel brings sincerity and warmth to the role of Sue Lee, a widow who becomes a beacon of hope for the Bushwhackers. While her performance is understated, it effectively conveys Sue Lee’s strength and adaptability in the face of overwhelming adversity.

Themes: Loyalty, Identity, and the Cost of War

1. Loyalty and Betrayal: The film examines the fluidity of loyalty during wartime, particularly as characters grapple with conflicting allegiances and personal relationships.
2. Identity and Belonging: Jake’s outsider status as a German-American fighting for the South mirrors the larger complexities of identity and cultural divisions in the Civil War.
3. The Human Cost of War: Through its focus on guerrilla warfare and personal relationships, the film emphasizes the devastating impact of war on individuals and communities.

Direction and Cinematography: A Visually Striking Masterpiece

Ang Lee’s direction is both intimate and expansive, capturing the brutality of war while delving deeply into the emotional lives of the characters. The cinematography by Frederick Elmes is breathtaking, showcasing the stark beauty of the Missouri-Kansas landscape with naturalistic lighting and sweeping vistas. The film’s attention to historical detail, from costumes to weaponry, enhances its authenticity.

Key Moments That Define Ride with the Devil

1. The Lawrence Massacre: The film’s depiction of this infamous event is unflinching and harrowing, underscoring the horrors of war and the moral ambiguities faced by the Bushwhackers.
2. Jake and Holt’s Bond: The evolving friendship between Jake and Holt is one of the film’s emotional highlights, exploring themes of trust and mutual respect.
3. Sue Lee’s Resilience: Sue Lee’s determination to rebuild her life amid the chaos provides a hopeful counterpoint to the film’s darker moments.

Strengths of Ride with the Devil

1. Complex Characters: The film’s protagonists are deeply flawed and multidimensional, making their journeys compelling and relatable.
2. Stunning Visuals: The cinematography and production design immerse viewers in the historical setting.
3. Nuanced Storytelling: Ang Lee’s restrained direction allows the story’s emotional weight to resonate without resorting to melodrama.
4. Jeffrey Wright’s Performance: Wright’s portrayal of Daniel Holt adds depth and humanity to the narrative.

Weaknesses of Ride with the Devil

1. Pacing Issues: The film’s deliberate pacing and introspective tone may feel slow to some viewers.
2. Underutilized Characters: Certain characters, such as Jewel’s Sue Lee, could have benefited from more development.
3. Limited Audience Appeal: Its focus on guerrilla warfare and moral ambiguities may not resonate with those seeking a more traditional Civil War epic.

Legacy and Reception

While Ride with the Devil received mixed reviews upon release, it has since gained a cult following for its nuanced storytelling and exceptional performances. Critics have praised its authenticity, emotional depth, and willingness to explore lesser-known aspects of the Civil War. The film remains a standout entry in Ang Lee’s diverse filmography.

Fun Facts About Ride with the Devil

1. Historical Accuracy: The film is based on Daniel Woodrell’s novel, which was inspired by real events and figures from the Civil War.
2. Jewel’s Acting Debut: This was the singer-songwriter’s first film role, marking a departure from her music career.
3. Filming Locations: Shot in Missouri and Kansas, the film’s locations were chosen to reflect the historical accuracy of the story.

Conclusion: A Gritty and Thoughtful Civil War Drama

Ride with the Devil (1999) is a visually stunning and emotionally resonant film that offers a unique perspective on the American Civil War. With its complex characters, nuanced storytelling, and exceptional performances, the film stands as a testament to Ang Lee’s skill as a filmmaker. While its introspective tone and deliberate pacing may not appeal to all viewers, its exploration of identity, loyalty, and the human cost of war ensures its place as a thought-provoking and memorable historical drama.