Ben Stiller Says This ’80s Box Office Bomb Was His Best Movie Experience

Ben Stiller has built a long and versatile career—Tropic Thunder, The Secret Life of Walter Mitty, Severance—but ask him about his favorite time making a movie, and you’ll get an unexpected answer: 1988’s Fresh Horses.

The lesser-known Brat Pack-era drama flopped hard at the box office, but for Stiller, it was a turning point. Speaking on The Prof G Pod With Scott Galloway, the actor and director said it was the only time he truly thought he’d made it.

“I was like, ‘Oh man, I’m going to be in the Brat Pack. I’m going to be in the movies. This is it. This is my moment,’” Stiller recalled.

A Cast of Twenty-Somethings Just Having Fun

Fresh Horses starred Andrew McCarthy and Molly Ringwald, reuniting after Pretty in Pink. The plot followed McCarthy’s college student as he left his fiancée to pursue a mysterious young woman (Ringwald), only to find out she was already married. Stiller played Matt’s wisecracking best friend, Tipton.

The film bombed. But to Stiller, the experience was unforgettable.

“The movie just tanked, but it was, literally to this day, my favorite experience ever making a movie,” he said.

Three Months of Freedom

The film was shot in Kentucky, and for Stiller, it was less about career momentum and more about the moment. “It was the dream,” he said. “We were all twenty-somethings making a movie, having fun, hanging out, hooking up.”

While it wasn’t the breakout he imagined, it gave him an early footing in Hollywood. He soon landed a short-lived stint on SNL, then found his voice behind the camera with 1994’s Reality Bites. His first true box office success wouldn’t come until 1998’s There’s Something About Mary.

Sometimes It’s Not About the Hit

Fresh Horses might be a footnote in Brat Pack history, but for Stiller, it was the kind of youthful, chaotic, all-in experience that Hollywood doesn’t offer much anymore.

This story was originally reported by Men’s Journal on Sep 2, 2025, where it first appeared in the Entertainment section. Add Men’s Journal as a Preferred Source by clicking here.