Starring: Kiefer Sutherland, Woody Harrelson, Ernie Hudson

Director: Gregg Champion
Released: 1994

Mood: If you’re too burnt out to think straight and the most you can handle is Woody Harrelson making dick jokes while Kiefer Sutherland quietly tolerates him.


Sometimes you pick a Western because even though you haven’t seen it, you know exactly how it will go. That was me with The Cowboy Way.


I found this DVD at a thrift store, which, if you follow my reviews, you know is where I like to ‘rescue’ abandoned Westerns. I was doing the slow crab-walk along the shelves, my neck craned painfully sideways, reading the hundreds of skinny DVD titles. I spotted the word ‘cowboy’ and grabbed it.


The back of the DVD jacket shows Kiefer Sutherland and Woody Harrelson in Stetsons, on horseback, careening along a pedestrian path beside the Hudson River, with the famous skyline in the background. Very New York, very west-meets-east. It looked gimmicky and stupid, which made it a great contender for my ‘hated it’ category.


Unfortunately, I don’t outright loathe it. It’s not winning any awards (except for several dishonourable mentions), but I just can’t hate Kiefer. Somehow he and Ernie Hudson keep The Cowboy Way from being a total fail – but just barely.


photo of the Cowboy Way DVD


The opening credits of The Cowboy Way blast rock n’ roll that shouts “we’re here for a good time!” The soundtrack features Bon Jovi – the driving force behind Kiefer’s iconic ‘90s Western hit, Young Guns – plus Blind Melon, Travis Tritt, INXS, En Vogue, the Allman Brothers, and George Thorogood.


We learn that Pepper (Woody Harrelson) and Sonny (Kiefer Sutherland) have been best friends and rivals since they were wee cowboys wrasslin’ hogs. But at some point Pepper became a liability, and he no-showed at a major team roping event that cost Sonny his dream. They haven’t spoken since.


Sonny’s close friend Nacho (Joaquín Martínez) is involved in a scheme to get his daughter smuggled into the States from Cuba. He’s being bamboozled by the smugglers and disappears, so Sonny decides to drive from New Mexico to New York to help him. Pepper won’t get out of Sonny’s truck, so naturally Sonny has to take him along.


On the road they have thin moments of bonding that don’t quite explain this friendship. You know you’re supposed to want them to make up, but Pepper is a huge ass and you never once believe that he deserves Sonny.


When they get to New York, shit goes crazy. Nacho is gone, and his daughter is being held captive in a sweatshop factory. The boys have to take on a sleazy New York crime boss, with the help of a Black cop (Ernie Hudson) who grew up idolizing rodeo legend Bill Pickett.


Fancy restaurants. Rich women. Male strippers. Can Sonny save the conveniently gorgeous daughter? Is Pepper just a piece of crap? I’m just pretending there’s suspense – you know from the start how it will turn out, and you’re correct.


illustration of a fancy moustache


Kiefer Sutherland can do no wrong. This is just a fact in my book.


He’s that perpetual good guy, and his portrayal of Sonny is not too far flung from his portrayal of Doc Scurlock in Young Guns. He’s sweet, he’s haunted, you want to hug him. Honestly, the rest of the movie just feels kind of forced on him, yet he works with the material as much as he can.


In the ‘90s Woody excelled at being a mimbo, and Pepper is exactly that. It’s like they knew when they wrote the script who they wanted, and styled Pepper based on his previous roles.


Much of the humour doesn’t age well – seriously, go read the movie quotes on IMDb – and it’s mostly Woody’s bits. TONS of dick jokes, like dick and gay jokes galore, and some Native stereotyping when he’s dressed as a ‘chief’ for dirty role-playing with a buckle bunny.


We all know that Woody eventually outgrew his pretty-boy typecast. You almost feel for him here, performing lines that do NOTHING for the story and make him look like a f*cking idiot.


Ernie Hudson is great in the too-small role of officer Sam ‘Mad Dog’ Shaw. He does an excellent job of making you want to follow HIS character out of the scenes.


illustration of a fancy moustache


Literally nothing about The Cowboy Way is plausible, and as soon as you stop searching for a real plot you’ll be in a much better place to sit through it. If you want plot, go watch Kiefer in Forsaken.


Don’t even get me started on how as soon as Sonny and Pepper commandeer horses for the final chase, they instantly know how to gallop the perfect path through New York’s busy streets to keep up with a f*cking subway train, having never been to New York before in their lives or taken the subway or even looked at a map.


The Cowboy Way isn’t a movie I’ll put on again. It has quite a few lowbrow laughs and it was pretty exciting to watch that utterly unrealistic horseback chase through New York. But for the most part you’re just annoyed by Woody and wondering why they didn’t make it just about one displaced cowboy and a Black cop in the NYPD Mounted Unit, fighting crime in the mean streets of ‘90s New York City. Now THAT’s a movie I want to see.