Tobey Maguire's Criminally Underseen Western Didn't Deserve To Flop At The Box Office

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Prior to suiting up as Spider-Man, Tobey Maguire starred in a revisionist Western that failed to make much of an impact. Directed by Ang Lee, "Ride with the Devil" endured a mismanaged theatrical release that led to it flopping. But it's far from one of Lee's worst films. In fact, the story of Maguire's Southern scion Jake Roedel becoming a guerrilla fighter for the Confederacy is arguably one of the most unfairly overlooked features in the director's estimable filmography.

After making what became known as his "Father Knows Best" trilogy in Taiwan, Lee made his Hollywood breakthrough with 1995's "Sense and Sensibility" which debuted to widespread praise and set him up for his second American feature, 1997's "The Ice Storm." That drama starred Kevin Kline and Sigourney Weaver alongside Tobey Maguire, marking the first time the latter and Lee worked together. Once again, the director enjoyed an excellent critical response and was no doubt expecting the same for his next film.

1999's "Ride with the Devil" saw Lee re-team with Maguire for a revisionist Western that represented somewhat of a departure for the Taiwanese filmmaker. Not only was it his first Western, it was his first film to earn a less than stellar critical response. Reviewers weren't necessarily dismissive of the film, but they weren't as impressed as they had been with Lee's previous efforts. What's more, "Ride with the Devil" bombed at the box office, earning well under $1 million in theaters on a $38 million budget. It deserved better.

As you might expect, given how popular the genre was in its heyday, film history is littered with Westerns that should have never flopped. By the late 1990s, however, oaters had almost completely fallen out of favor. Indeed, just two years after "Ride with the Devil" debuted, Roger Ebert was convinced the Western had died (though, in that case, he had just seen the laughably bad "American Outlaws"). Ang Lee's film, on the other hand, was a quality late-'90s Western that proved the genre still had some creative life left in it. The only problem? Nobody saw it.

Based on Daniel Woodrell's 1987 historical novel "Woe to Live On," the film follows Tobey Maguire's Jake Roedel and Skeet Ulrich's Jack Bull Chiles as they join the First Missouri Irregulars, aka the Missouri Bushwhackers, following the outbreak of the Civil War. The film begins with pro-Union Jayhawkers setting fire to Jack's family plantation and killing his father, prompting the pair to pursue vengeance via the Confederate militia. Jeffrey Wright plays Daniel, a former enslaved person who fights as part of the Bushwhackers alongside the man who freed him, Simon Baker's George Clyde.

The film is less interested in Jake and Jack's quest for vengeance than it is in exploring the various militia members' complex motives for being part of the group. Jack does fall in love with war widow Sue Lee Shelley, played by Jewel in her feature film debut, but like the action in the movie, Lee doesn't exaggerate the romance. It doesn't make for the most thrilling Western you'll ever see, but it allows Lee to play to his strengths interrogating familial — or in this case proto-familial — relationships. He seemed to impress a fair few critics in the process.

"Ride with the Devil" has a 65% critic score based on 68 reviews on Rotten Tomatoes. For the most part, critics seemed to like Ang Lee's Western, even if they weren't as effusive as they'd been for his previous films. In his two-star review, Roger Ebert opined that "Ride with the Devil" was "not a very entertaining movie" and even went as far as to call it a "long slog unless you're fascinated by the undercurrents." But it seems many reviewers were fascinated by the undercurrents, with Peter Matthews of Sight & Sound praising the film's "texture of fine-grained observation that brings history to life on the molecular level." Meanwhile, Variety's Todd McCarthy found it "admirably expressive" and Andrew O'Hehir of Salon described it as "one of the most interesting and least dogmatic" Civil War movies ever made.

Sadly, distributor USA Films wasn't quite as enthused. According to Bomb Report and Box Office Mojo, "Ride with the Devil" debuted in 11 theaters, earning just $64,159 in its opening weekend. The film eventually expanded to 60 theaters but it wasn't enough to change its fortunes, leaving Lee's Western with a total box office take of $635,096 (though international figures aren't available).

Dumping thoughtful revisionist Westerns seemed to be in vogue in the late '90s/early 2000s, as Warner Bros. would soon pull the same trick on one of the best movies of the era with Brad Pitt's Western "The Assassination of Jesse James by the Coward Robert Ford." Though it wasn't quite the triumph Pitt's film represented, "Ride with the Devil" deserved much better than it got and is well worth revisiting or, indeed, watching for the first time if, like everyone else, you've not seen it.