New York City in the early nineties was a specific kind of grime. It was loud. It was crowded. It was the absolute last place you’d expect to find two championship rodeo stars from New Mexico chasing down a missing girl. But that’s exactly the setup for The Cowboy Way, a 1994 flick that basically defined the "fish out of water" trope for a generation of cable TV surfers.
Look, it’s not Citizen Kane. Nobody is claiming it is. However, if you grew up watching Woody Harrelson and Kiefer Sutherland trade barbs while riding horses through the streets of Manhattan, you know there’s a certain magic there that modern CGI-heavy comedies just can't replicate. It’s got heart. It’s got grit. And honestly? It’s got Woody Harrelson in a pair of tight jeans doing trick roping. What more do you want?
The film follows Pepper Lewis (Harrelson) and Sonny Gilstrap (Sutherland). They’re best friends, or at least they were until life and a few bad decisions got in the way. When their friend Nacho Salazar disappears after heading to NYC to pay off a coyote and bring his daughter to the States, the duo decides to head East. What follows is a chaotic, sometimes ridiculous, but always entertaining collision of rural grit and urban cynicism.
Why The Cowboy Way Failed at the Box Office but Won on VHS
When people talk about 1994 in film, they usually mention Pulp Fiction, The Lion King, or Forrest Gump. Those were the giants. The Cowboy Way kind of got trampled in the stampede. It pulled in about $21 million domestically against a budget that was likely significantly higher once you factor in the logistics of filming in New York. Critics weren't kind either. Roger Ebert famously gave it two stars, suggesting the movie was a bit too predictable for its own good.
But critics often miss the point of a "vibes" movie.
The chemistry between Sutherland and Harrelson is the whole engine. Sutherland plays the "straight man" Sonny with a brooding, focused intensity that balances out Harrelson’s chaotic, skirt-chasing, thrill-seeking Pepper. It’s a classic dynamic. Think Lethal Weapon but with more manure and Stetson hats. While the plot—involving a sweatshop ring and a villainous Joaquin de Almeida—is standard action-movie fare, the character moments are where the film actually breathes.
There’s this scene where Pepper tries to order a meal in a high-end restaurant. He’s confused by the portions. He’s annoyed by the pretension. It’s a trope, sure, but Harrelson sells it with such genuine "aw shucks" charisma that you can’t help but root for him. He isn't playing a caricature; he’s playing a guy who genuinely doesn't understand why people live like this.
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The Real New York vs. The Hollywood Version
Filming a movie like The Cowboy Way in New York City during the 90s was a logistical nightmare. Imagine trying to coordinate a horse chase through the Midtown traffic. The production actually utilized several iconic locations, including the Waldorf Astoria and the old shipping docks.
One of the most authentic parts of the movie—oddly enough—is the depiction of the immigrant experience through the character of Nacho and his daughter, Teresa. While the movie is a comedy-action hybrid, it touches on the very real dangers of human trafficking and the exploitation of undocumented workers in the garment industry. It doesn't get too deep into the weeds of social commentary, but it provides a grounded motivation for the protagonists. They aren't there for a vacation; they're there for a rescue.
The Stunt Work and Rodeo Authenticity
You can't have a movie called The Cowboy Way without some actual cowboying. Woody Harrelson actually grew up in Texas, and while he wasn't a pro roper, he took the training seriously. Kiefer Sutherland, on the other hand, became quite the rodeo enthusiast in real life.
Sutherland actually went on to compete in USTRC (United States Team Roping Championships) events. He didn't just play a cowboy; he leaned into the lifestyle. That authenticity shows up on screen. When they’re handling the ropes or sitting in the saddle, they don't look like actors who just finished a two-week "boot camp." They look like men who know their way around a horse.
The Soundtrack: A Time Capsule of 1994
The music in this film is a wild ride. You’ve got The Allman Brothers Band, En Vogue, and even Jeff Beck. It’s a weirdly eclectic mix that perfectly mirrors the clashing worlds of the film.
- "Good Times" by Edie Brickell — Sets that laid-back, somewhat hippie-cowboy tone.
- "The Cowboy Way" by En Vogue — A total 90s R&B pivot that feels strange but somehow works in the credits.
- "Wild Night" — The Van Morrison cover by John Mellencamp and Me'Shell Ndegéocello was actually a huge hit around the same time, though its association with the film helped cement its radio presence.
Music was such a massive part of 90s marketing. Back then, a soundtrack could sell a movie just as much as the trailer. For The Cowboy Way, the soundtrack tried to bridge the gap between country-rock fans and the MTV generation. It was a bold move that mostly paid off in terms of cultural footprint, even if the box office numbers didn't reflect it.
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The Villain Problem: Why We Love to Hate Manny
Every buddy cop or fish-out-of-water story needs a foil. Enter Joaquin de Almeida as Manny Vasquez. De Almeida is one of those actors who can look sophisticated and terrifying at the same time. He plays the wealthy, corrupt businessman who thinks he’s untouchable because he’s in the "civilized" world of New York.
The climax of the film—which involves a horse-versus-train chase—is arguably one of the most underrated action sequences of the decade. It’s practical effects. It’s real horses. It’s real stuntmen. There’s a weight to it that you just don't get with modern digital compositing. When those horses are galloping alongside the tracks, you feel the thud of the hooves.
Where Can You Watch it Now?
Finding The Cowboy Way today can be a bit of a treasure hunt. It’s not always on the major streaming platforms like Netflix or Max. Usually, you’ll find it tucked away on "FAST" channels (Free Ad-supported Streaming Television) like Tubi or Pluto TV.
It’s the quintessential "Saturday afternoon" movie. You know the type. You’re flipping channels, you see Woody Harrelson wearing a tuxedo with cowboy boots, and you decide, Yeah, I’ve got two hours for this.
Common Misconceptions About the Movie
A lot of people confuse this film with City Slickers. I get it. Both came out in the early 90s. Both involve city life and cowboys. But where City Slickers is a mid-life crisis movie about guys going to the country, The Cowboy Way is an action-adventure about country guys coming to the city.
Another mistake? Thinking it’s a pure parody. It’s not. It takes its action beats seriously. The stakes feel real, especially regarding the fate of the girl they are trying to save. It balances the humor with a genuine sense of urgency.
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Actionable Takeaways for Movie Buffs
If you’re looking to revisit this 90s gem or experience it for the first time, here is how to get the most out of it:
- Watch for the Chemistry: Pay attention to the improvised-feeling banter between Sutherland and Harrelson. That wasn't all on the page; a lot of it was their natural rapport.
- Check the Practical Effects: Look at the horse stunts in the final act. In an era of Marvel movies, seeing real horses on Manhattan streets is a trip.
- Spot the Cameos: There are several faces from 90s television and NYC character actors who pop up in the background. It’s a "who’s who" of "hey, it’s that guy!"
- Context Matters: Watch it as a double feature with Hard Way (1991) or City Slickers. It fits perfectly into that specific era of high-concept Hollywood comedies.
The Cowboy Way is a reminder of a time when movies didn't need to set up a cinematic universe to be successful. They just needed two stars, a solid hook, and enough heart to keep you watching. It’s about loyalty. It’s about friendship. And yeah, it’s about how sometimes, the only way to solve a problem in the Big Apple is to do it the old-fashioned way.
To truly appreciate the film, look past the 90s fashion and the slightly dated soundtrack. Focus on the core story: two guys who realize that no matter how far they stray from home, they’ll always have each other’s backs. That's a universal theme that never goes out of style.
Next Steps for the Nostalgic Viewer:
Check your local digital libraries or "free with ads" streaming services to find a copy of the film. If you're a physical media collector, the Blu-ray releases often have better color grading that preserves the gritty look of 90s New York much better than the standard definition streams. After watching, look up Kiefer Sutherland’s real-life rodeo stats—it’ll make his performance in the film feel even more impressive.