Ride With the Devil (1999): Ang Lee’s Civil War Western

Ang Lee directed Ride With the Devil, a sprawling Civil War crime-gangster-western, scripted by James Schmaus, based on the book Woe to Live On, by Daniel Woodrell.

Our grade: B- (** out of *****)

Dealing with a subject rarely portrayed in such detail by mainstream movies–the escalating guerrilla warfare in Missouri at the onset of the American Civil War–Ride with the Devil qualifies as an honorable failure, an ambitious feature that suffers badly from various problems, including the miscasting of the leads.

Jake Roedel (eternally boyish Tobey Maguire) and Jack Bull Chiles (Skeet Ulrich) are friends in Missouri when the American Civil War breaks out. During a mayhem, Chiles’ father is murdered by Kansas pro-Union Jayhawkers.

The two then join the First Missouri Irregulars (aka the Bushwhackers, informal groups loyal to pro-Confederacy in 1861. They later meet George Clyde and former slave Daniel Holt, whose freedom Clyde had previously granted.

The Bushwhackers battle Jayhawkers using guerrilla warfare tactics while trying to evade their capture. The men manage to hide out in a coarsely-built shelter on the property of a pro-Confederacy family, the Evanses.

A young widow in the household, Sue Lee Shelley (singer Jewell in screen debut), becomes romantically involved with Chiles. When Chiles dies of wounds, Roedel escorts Shelley to a refuge, residence of the pro-Confederate Brown family.

The supporting performers–Jeffrey Wright, Jonathan Rhys Meyers, Jonathan Brandis, Jim Caviezel, and Mark Ruffalo–are far more interesting than the main characters.

Aiming for an intimate epic, Schamus’ script doesn’t provide significant links between the dominant figures and the broader political contexts in which they operate.  Moreover, the narrative is too diffuse, and uncharacteristically for a Lee film, unfocused, rambling along from one violent scene to another.

As a result, it’s almost impossible to get involved with any of the proceedings, problems which are aggravated by leisurely pacing and lengthy running time (138 minutes).

Reportedly, due to poor testing, the film never got proper theatrical distribution.  It was released by USA Films (Universal indie boutique), in November 1999, and played in few movie houses.

Mixed critical response did not help matters, either.

In 2010, The Criterion Collection released a restored digital transfer, which is longer, but the feature remains unsatisfying due to the aforementioned problems.