Chris Farley Ended His Comedic Career With A Major Western Flop Featuring A Friends Star

We may receive a commission on purchases made from links.

Chris Farley was only 33 years old when he passed away on December 18, 1997, the result of an overdose. Looking back, it all seemed tragically inevitable. His struggle with addiction had become so intertwined with his public persona that it was almost impossible to separate the man from the myth. By the fall of 1997, when he returned to host "Saturday Night Live," the show that had catapulted him to fame earlier in the decade, the entire cold open revolved around a joke about his mere ability to perform. Watching it unfold, I remember feeling a deep unease. Chris looked unwell—his voice raspy, as though his body itself was rebelling against him, rejecting the weight of the life he’d been living.

If you delve into Farley's story, you'll find that those closest to him did everything in their power to help him get sober. Yet, time and again, he found his way back to the party. His lifestyle, increasingly harsh and unforgiving, left its mark on him—from one film to the next, it was heartbreakingly evident. While "Tommy Boy" showcased his comedic brilliance, the promise of a film series featuring him alongside David Spade was tragically dashed by the disastrous "Black Sheep." Though "Beverly Hills Ninja" offered a modest improvement, it was clear that Farley was working harder than ever for laughs. What he truly needed was a romantic comedy like "The Wedding Singer," a project that could highlight his endearing sweetness just as much as his explosive energy.

On paper, Farley's next film appeared to be a step toward redemption. It was a historically grounded comedy inspired by the sophisticated humor of "Black Adder." Partnered with Matthew Perry (then at the height of his "Friends" fame) and directed by the legendary Christopher Guest, this project seemed poised to showcase Farley’s talents beyond slapstick. For once, he might not have had to rely solely on physical comedy to elicit laughter. But then they made the movie.

The most jarring aspect of "Almost Heroes," which limped into theaters on May 29, 1998, is that Christopher Guest didn’t lobby to remove his name from the credits. At what feels like a contractually mandated 90 minutes, this frontier comedy about two hapless explorers bumbling across America lacks cohesion and rarely rises above mediocrity. Its misshapen structure, tonal imbalance, and lackluster humor make it a forgettable entry in both Farley’s and Guest’s careers.

As Thomas R. Wolfe, one of the film’s credited screenwriters, recounted in Tom Farley Jr. and Tanner Colby's book "