Overlooked Greatness: 'American Outlaws' (2001)

**This article also appears on RopeofSilicon.com.**

I can guess what you must be thinking. A cowboy movie? With Colin Farrell? Yes, you’re right. It was an unknown Irishman playing a classic American cowboy—and Jesse James, to boot. It’s everything wrong, and perhaps that’s why, seven years ago when I first heard about it, I was immediately intrigued.

Unless watching gay cowboys who are in love with each other, I’ve never been that much of a Western fan. I’m not saying that to immediately discredit any words I might share about this particular Western (though that might be the result). I’m saying it, in fact, to bolster the film’s credibility. It didn’t spin itself as an historical drama. It’s a popcorn flick with some horses thrown in, and if you think of it that way, you’re already saddled up for a smoother ride. But if you need further convincing, hopefully that’s where the following Five Factors of Greatness come in.

1. Colin Farrell: We know the Hollywood Talent Trajectory™ by now: Early Speculation of Star Status leads to Quagmire of Cocaine, which leads to 100 Years of Solitude, which leads to Awesome Phoenix-Like Rebirth. Note those who spun out early (River Phoenix) and those who have finished the journey (Mickey Rourke). Having just won a Golden Globe for his wonderful portrayal of a hitman with heart in the BAFTA Award-winning In Bruges, Farrell has come out of the quagmire of cocaine and is on his way back to potential Phoenix Status. And I’ll argue that American Outlaws, Farrell’s second American film, was a hint to the masses about what was in store. Though it might be a stretch to say he was “discovered” thanks to this film (he did act for Schumacher a year prior in Tigerland), it definitely helped put him on the HTT ™ and defined him as a heartthrob to watch. In Outlaws we get to see Farrell act two roles: swashbuckling ne’er do well and hopeless romantic. It’s sweet, endearing, youthful and exciting. Someone else might have made more sense for a Jesse James, but Farrell made this Jesse James all his. (And as an aside: Kathy Bates plays his mom. Love her.)

2. Dialogue: There are some truly great lines in this film. From “Hey! You wanna die?” to “It’s going to be a long [insert season],” Outlaws always makes me smile. It is memorably quotable, and the only reason people don’t think about the dialogue’s repeatability is—well, there are two reasons. One, not enough people have seen this movie, and two, when it isn’t Will Ferrell-funny or Meryl Streep-dramatic, less people care to play along. I know quotes from small films like Napoleon Dynamite or Juno have eked through, thanks to the portrayal of the offbeat American family behaving in an offbeat way, so there’s got to be room for an offbeat American western in our memories somewhere. Right? I love “This is one doodle that can’t be undid, Home Skillet” (Juno), just as much as I love, “Younger-James gang? Is there an older James gang?” And that’s why I watch and re-watch this movie every year. The quotes never get old, and the fun never wanes.

3. Robin Hood factor: The heart of this Jesse James story is simple. When the railroad company tries to shoulder its way through his family’s homestead, Jesse and his band unite to bring them down, one bank at a time, while providing their neighbors with both physical and financial security. In short, he and his posse steal from the rich and give to the poor. Well, there’s something about stickin’ it to the Man that always makes for a winning plotline. We like the underdog (or the “slumdog,” if you will), the upstart, the gangster with a heart of gold. And you can’t help but root for him in his quest—especially if he’s got a face like Colin Farrell.

4. Butchering of history for entertainment’s sake: Like I mentioned before, Outlaws never intended—or at least I hope it didn’t intend—to be an historical drama. It is neither a history lesson nor a biopic. Who knows if it got the Jesse James and the Younger Brothers’ story right? I’m going to assume it did, pop some popcorn, and move on with my movie night. It’s this same ability to ignore the details in favor of some amusement that lets us enjoy Shakespeare in Love (another perennial favorite of mine). And though, clearly, Shakespeare is the “better” film, both that film and this one operate with the same premise: get the basics down, and then have a laugh. If you like a bit (or a lot) of cheese with your popcorn, Outlaws will taste just right.

5. The tagline and the trailer. They are both seriously so bad, the film just has to be good. Now, obviously when I say “good,” I don’t mean Amistad-good. But in its own, wonky way, American Outlaws is great, and both the tagline and trailer tell you why. With all the guns and action, Outlaws channels more than a bit of 1988’s Young Guns but it uses one-too-many Moby songs (i.e., one) to get to this point. Watch the trailer, and you won’t be able to figure out if you’re in post-Civil War America or in 2001: A Musical Odyssey, in which the members of the band Saliva decide to become cowboy bank robbers. But filter your confusion towards the tagline of the film: “Bad is Good Again.” Um…that says it all. Outlaws doesn’t take itself seriously, and that’s its strength. Bad is good again. And I’m watching.

I think the leading fault of American Outlaws is that it doesn’t quite embrace a genre. Above, I referred to it as an “offbeat American Western,” but that’s not entirely how it sold itself. Outlaws tight-roped between offbeat and ordinary, and there was its undoing. It wasn’t quite clear if viewers should take the film seriously or not. Was it a true telling of the legend of Jesse James? Was it a farcical remake of an American tall tale? Or was it just another shoot-‘em-up comedy with some famous names haphazardly thrown in? Unwilling to pick sides, Outlaws alienated most critics and viewers alike, succumbing to meager box office receipts and thus, obscurity.

But to this day, American Outlaws is the most watched film I own in my DVD collection. Perhaps that’s a little weird. But that’s not to say it’s my favorite film; it just never really gets old to me. Every time Scott Caan shouts, “Let’s ride!” I get into it all over again. It is familiar and fantastic, and it’s truly so bad it gets better every time.