"Ride with the Devil" (Ang Lee, 1999) The story of Quantrille's Raiders and the Missouri Irregulars were a sorry part of the Civil War story, but its tales of guerilla raids between two groups, the "bushwhackers" and the "jayhawkers," criss-crossing the Kansas-Missouri border, it's history with Quantrille, Bloody Bill Anderson and Jesse James and the murderous raid on Lawrence, Kansas in 1863 have been explored, somewhat tangentially, as the first battles in the Outlaw West.
Director Ang Lee may seem an odd choice for a Western of this nature, but such was the case when he directed "Sense and Sensibility." Versatile, facile, and able to make universally accepted films across genres, there seems little Lee cannot succed at whether period romance ("Sense and Sensibility"), spy-noir ("Lust/Caution"), martial arts flick ("Crouching Tiger, Hidden Dragon"), even cross-blending sci-fi/horror and superhero movies ("Hulk").
"Ride with the Devil," with a screenplay by James Schamus (now head of Focus Features) was not a box-office success when it opened, perhaps as it was an unconventional western with controversial elements: four young people, Jake Roedel (Tobey Maguire), Jack Bull Chiles (Skeet Ulrich), George Clyde (Simon Baker), and Daniel Holt (Jeffrey Wright) all find themselves fighting as Confederate guerillas during the Civil War as "bushwhackers," not so much as they believe in the Southern cause—Holt is a freed slave—but because of issues with loyalty, friendship and attacks on their families. Soon, they're conducting murderous assaults on established Union positions with deadly accuracy, which Lee stages with a brutal efficiency: quick cuts, fast pace and attention to the damage a round bullet can inflict.
Housed for the winter in a make-shift shelter, they are looked after by Southern sympathizers, with particular interest paid by a war-widow named Sue Lee (Jewel), who begins an affair with Chiles and offers support and food during the harsh winter. It's a nicely paced gritty portrayal of life led as an outlier, and the elements are mixed as to keep one guessing about what will happen next.
The revelation here is Tobey McGuire, heretofore usually playing callow youths (which is why he was picked to play Peter "Spiderman" Parker), here he's got a versatile range of situations, starting out as a disillusioned follower, then his own man of a kind, backed by a steely gaze that turns durn creepy at times, and an "on-the-edge-of-cracking" voice that lolls over dialogue. Nice work, and Lee makes the most of him, using the boyish qualities of McGuire for moments of humor, terror and combinations of both.