By John H. Foote
27. RIDE WITH THE DEVIL (1999)
One aspect of the Toronto International Film Festival I have always loved (and there are so many) is discovering small films that might get a release later in the year, to little fanfare, despite solid, even rave reviews. Such was the case in 1999 with two brilliant films: Ang Lee’s magnificent Civil War epic Ride with the Devil, and Steven Soderbergh’s The Limey. The former is a brilliant intimate epic about friendship and loyalty during the Civil War and is among the very best of that genre.
It seems every working director in film has a fine film that is virtually forgotten when discussing their filmography. For Ang Lee, when his films are discussed Brokeback Mountain (2005), his masterpiece, and Life of Pi (2012) are the most frequently discussed followed by his magical Crouching Tiger, Hidden Dragon (2000) and The Ice Storm (1997). Sadly, rarely, if ever entering the conversation is this film Ride with the Devil, which is easily among the finest films made about the impact and strife of the Civil War, but more the friendships and loss during that time.
Jake Roedel (Tobey Maguire) is of German descent, but considers himself fully southern, and is more than willing to fight against the invading Northerners threatening to take away a way of life. With their genteel manners, respect for women, and beautiful manner of speaking, the South was a fascinating place, scarred by the American Holocaust that was slavery. When Jake’s best friend’s family is massacred, he joins Jack (Skeet Ulrich), becoming part of a guerilla band of outlaws who attack Northerners whenever they find them. They are joined by Clyde (Simon Baker) and his friend Holt (Jeffrey Wright), a slave he bought and freed, his best friend since they were children together. Among their group are Bick Mackeson (Jonathan Rhys Meyer), a murderous psychopath who is filled with sadism and bloodlust, and Black Jack (Jim Cavaziel) a deeply angry man who has lost family to the Northern soldiers.
With winter coming they go into a hibernation, digging a shelter in the earth and live quietly, avoiding the roads and the Northern patrols. They are helped by families believing in their cause, who feed them and help them stay warm and safe. It is here Clyde is often gone, seeking the attentions of a nearby young lady he knows, while Sue Lee (Jewel) begins coming around the shelter with their food, and to see Jack Bull. This permits a friendship between Jake and Holt to emerge, and the more they are together, the deeper the friendship becomes. During a skirmish in the spring Jack Bull is shot, badly, and Jake and Sue Lee attempt to care for him, to mend the mangled arm. With his eyes filled with tears, Jake begins to amputate his best friend’s arm, but the wounded man cannot handle the trauma and dies.
Jake and Holt return to the Bushwackers where they learn that Black Jack, enraged at the deaths of many women burned alive in a church by Northerners has called for the assistance of Quantrill’s Raiders, a dangerous and unmerciful group led by the Custer-like Colonel Quantrill. For their target they choose Lawrence, Kansas, a peaceful town, one you would never expect to have anything to do with the war. Sending the vicious Bitt into the town to start the attack, the Raiders follow, killing all men and young men, literally dragging them out into the street and killing them. Less than an attack, than an absolute slaughter, it is frightening to see such anger and rage, cold blooded murder for no other reason than they can. Watching Bick Mackeson gleefully walk through the streets killing, is seeing a vicious young man in his element. Deeply psychotic, long ago a sociopathic maniac, Mackeson kills for the sake of killing, enjoying it, even basking in the momentary glory, if there is glory in this type of killing. He bursts into a small diner where Jake and Holt are eating eggs prepared by the terrified owners, and Bick orders the man outside, to kill him, but Jake stops him. Bick threatens Jake with death and Jake at once pulls his gun and aims it directly at Bick, daring him to do anything. Bick leaves, but an enemy of the dangerous killer has been made in Jake. Protected by Holt, Jake knows Bick wants him dead and talks terrible talk against him to Black Jack, who knows what he is hearing is wrong. When Clyde is killed, shot through the neck, Jake and Holt head back to the farm where Sue Lee is staying to find her with child (Jack Bull’s) but everyone living there is convinced it is Jake’s. A wedding is hastily thrown together, and just like that, Jake finds himself a man with a family. Though Holt chuckles at the whole event, he also knows it is the beginning of the end of their relationship and travels.
Loading up a wagon, Jake, Holt and Sue Lee travel through dangerous territory, Northerners everywhere, and during a brief stop in the forest they encounter Bick Mackeson, though he is much changed. Defeated, cynical and bitter, he seems to no longer pose a threat to Jake, but the two men take no chances and send him on his way at gunpoint.
Holt and Jake finally go their own way, Holt in search of his mother to buy her freedom, Jake to settle and forge a life with his new bride and to raise Jack Bull’s child. Each man parts the other with tears growing in their eyes, realizing a dear friend is parting, perhaps never to be seen again. As brothers they part, friends forever.

Ang Lee’s Ride with the Devil was among the finest films I saw in 1999 yet failed at the box office and, come Oscar time, was ignored in every single category. Are the members of the Academy not to celebrate the best? So how was this and so many others ignored, and then snubbed? It makes no sense to me that a film such as this was so ignored. None.
Tobey Maguire displayed an astonishing range that he has rarely had the chance to explore on screen. He was superb here as Jake, but then went on to great fame in Spiderman (2002) and even greater acclaim in Spiderman 2 (2004), often hailed as the greatest comic book superhero film ever made. Maguire has what Di Caprio possesses, an absolute ability to nail the character, to make every line seem true, to authentically create the character making him true. His evolution as Jake is superb, moving easily from young warrior to a growing man who has killed fifteen men but knows nothing of love and real life.
Skeet Ullrich never really found great fame as an actor, perhaps due to his striking resemblance to Johnny Depp. But here as Jack Bull he is the epitome of Old Southern manners and courtly ways. Listen to him speak, he perfectly creates the southern manner of speaking in every way. His performance is superb, creating a young man who loses everything early in the film, and therefore has nothing to lose. Sadly, Ullrich returned to relative obscurity.
Jewel, the pop star, gives a fine lived-in performance, nothing flashy, no grand moments just a very fine, realistic performance. We understand the attraction Jack has to her, and we further understand why Jake would agree to marry her and raise his friend’s child.
Rhys Meyer steals every scene he is in as Bitt Mackeson, portraying him as a psychotic, vicious killer who stops the blood with a stare. Once targeted there is a pretty good chance his prey is dead, as he is fearless, and certainly has no fear of death. It is a powerful, electrifying performance.
The best work in the film belongs to Jeffrey Wright as Holt, the slave freed by Clyde, and travels with his friend out of loyalty. The great evolution of Holt is when the film begins he is near silent, very much in the background, though when the fighting starts, he is in the thick of it, fearless, brave and always has Clyde’s back. But over the course of the film as the North takes control of the war, he becomes more outspoken and his friendship with Clyde erodes, as he becomes closer with Jake, the two men finally always together, but because they want to be, not out of any strange loyalty. Holt, much to his surprise, becomes Jake’s best friend, and their love for one another evident in each glance, each word. When they part ways, tears flow from their eyes, knowing they might never see one another again, each deeply aware of what the other man has meant to the other. Wright is a gifted actor, superb here, Oscar worthy, and has gone on to great work. He was astonishing in Angels in America (2003) and remarkable in Westworld (2013) for HBO.
Great films that never find an audience are not new, they have always been with us, and it is difficult to understand why. Ride with the Devil is such a film, recreating a time long gone with remarkable accuracy, a lyrical score, and absolute realism. That it is poetic and tells the story of an evolving friendship is a bonus. Possibly the greatest unseen film of the decade.

John H. Foote is a well-recognized Canadian film critic/historian who has been an active critic for 30 years. His deep love for the movies began at a very young age. He began his career as co-host of the popular TV show Reel to Real where he remained for nine years. While on TV he began dabbling in education, eventually ascending to Director of the Toronto Film School, where he also taught film history. After leaving the college to care for his wife, he returned to teaching at Humber College where he taught both Film History and Method Acting Theory. John has written two books: “Clint Eastwood – Evolution of a Filmmaker” and the upcoming “Spielberg – American Film Visionary”. He is currently working on two books, one about the films of the seventies and another on the films of Martin Scorsese. Through his career he has worked in TV, radio, print and the web. John has interviewed everyone in the industry (more than 300 interviews) except Jack Nicholson, he says sadly. Highlights include Martin Scorsese, Tom Cruise, Meryl Streep Robert Duvall, Jane Fonda, Francis Ford Coppola and Kathryn Bigelow.