Even Hollywood heavyweights like Ben Stiller can't help but feel starstruck when sharing the screen with a true icon. In a recent interview with TheEntBase, Stiller revealed that working with David Bowie on the 2001 comedy Zoolander remains one of the most cherished moments of his career.
"After decades in the industry, that collaboration with Bowie stands out as a true highlight," Stiller reflects. "He was incredibly generous and classy—everyone on set was completely mesmerized by his presence."
Ben Stiller, David Bowie, and Owen Wilson in the iconic 'walk-off' scene from 'Zoolander'. CBS via Getty
In the film, Bowie appears as himself, judging a hilarious runway "walk-off" between rivals Derek Zoolander (Stiller) and Hansel McDonald (Owen Wilson). He sets "old-school rules" and urges the models to "go to work," then meticulously takes notes on his palm as he watches their performances.
The scene takes a comedic turn when Hansel manages to remove his underwear without disturbing the rest of his outfit, leaving Bowie stunned. He later peers under Stiller's legs to disqualify Derek for failing to replicate the same trick.
Ben Stiller in a memorable scene from 'Zoolander'. Paramount Pictures/Getty
"I was shocked when he agreed to do it," Stiller admits about Bowie's cameo. "But he had a fantastic sense of humor and was very self-deprecating. I feel incredibly lucky to have had that brief time with him."
Stiller also emphasizes that Bowie's involvement gave Zoolander a level of credibility it wouldn't have had otherwise. "His presence in that scene added so much legitimacy to our movie," he says. "Without a doubt, it's been a career highlight for me."
Beyond Bowie, Stiller discusses working with other music superstars, including Ariana Grande in the upcoming Meet the Parents sequel, Focker In-Law. "Her energy was a great addition to this long-running franchise we hadn't touched in years," he notes. "She's super professional, knows comedy from her SNL experience, and was an absolute delight to work with."
Ben Stiller in London in 2025, reflecting on his diverse career. Max Cisotti/Dave Benett/Getty for Apple TV+
Stiller's latest venture pairs him with another singer: an Instacart ad campaign featuring Benson Boone. In the commercials, they play brothers with ambiguous European accents, vying for attention while singing about the app's Preference Picker feature.
Stiller has high praise for his co-star. "He's amazing. I really admired him," he says. "He's incredibly talented and has a wonderful, open-minded approach to trying new things. With little acting experience, he dove right into improvisation, making the collaboration a blast."
