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Ride with the Devil is a 1999 American war drama film directed by Ang Lee and starring Tobey Maguire, Skeet Ulrich, and Jewel. The movie is set in Missouri during the American Civil War and explores the complex issues of race, class, and loyalty that were prevalent during that time. The story follows Jack Bull Chiles (Ulrich) and Jake Roedel (Maguire), two young friends who join the Bushwhackers, a pro-Confederate guerrilla group led by William Quantrill (John Ales). Jack is a wealthy Southerner who fights to preserve his family's way of life, while Jake is a poor German immigrant who joins the rebels out of a sense of adventure and because of his friendship with Jack. They quickly rise through the ranks of the Bushwhackers and become key players in the organization.

However, as the war drags on and the violence escalates, Jack and Jake begin to question the morality of their actions. They find themselves caught in a web of conflicting loyalties, torn between their allegiance to the Bushwhackers and their growing sympathy for Union sympathizers, including Daniel Holt (Jeffrey Wright), a former slave who is now fighting for the Union Army.

As the war comes to an end, the Bushwhackers are forced to flee for their lives. Jack and Jake set out on a dangerous journey to find refuge in Texas, where they hope to start a new life. Along the way, they encounter numerous obstacles, both from the outside world and from within their own ranks.

One of the movie's main themes is the complexity of the issue of slavery and the different attitudes towards it among both the North and the South. The film shows how even among the pro-Confederate guerrillas, there were differences in opinion about the justification for fighting and the morality of owning slaves. This is exemplified in the character of Holt, who fought for the Union Army but also faced discrimination from within his own ranks due to his race.

Another theme is the impact of war on individuals and society as a whole. The movie shows how people on both sides of the conflict were affected by the violence and the destruction that it wrought. The senseless killing that occurs throughout the movie serves to emphasize the tragic nature of war and the toll that it takes on both soldiers and civilians.

The performances in the movie are excellent, particularly Maguire and Ulrich as the two young friends who are forced to confront difficult decisions and weigh the consequences of their actions. Jeffrey Wright is also outstanding as Holt, bringing a sense of dignity and restraint to a character who has suffered greatly but refuses to give up hope.

Overall, Ride with the Devil is a thought-provoking and emotionally powerful movie that explores the complexities of the Civil War from the perspective of those who fought in it. It is a testament to the talent of director Ang Lee and the cast, who bring the characters and the era to life with sensitivity and depth.

Ride with the Devil is a 1999 drama with a runtime of 2 hours and 18 minutes. It has received mostly positive reviews from critics and viewers, who have given it an IMDb score of 6.7 and a MetaScore of 69.