In the 2000s, it was virtually impossible to get past Ben Stiller. Since his big breakthrough with There’s Something About Mary in 1998, he’s starred in one comedy after another, reaching the peak of his career. His most iconic role may have been the eccentric fashion designer Zoolander. Many people also love it for the My Wife, Her In-Laws and Me series.
With a filmography of almost 100 films, he certainly counts one of the busiest actors of his time. He also proved himself to be a talented director with The Amazing Life of Walter Mitty. However, he still regrets a career mistake to this day.
Ben Stiller auditioned for My Cousin Winnie – and completely blew it
Far Out Magazine reported a few days ago that Stiller spoke about a major regret in his career in a Q&A about his last directorial project Severance:
I messed up my audition for My Cousin Winnie. That haunts me to this day.
He opened up about how he would have had the chance to star in the 1992 classic alongside Joe Pesci, Marisa Tomei and Ralph Macchio. This might have given rise to the chance to have his Breakthrough achieved 6 years earlier. Joe Pesci in particular was known at this point not only for his serious roles as gangsters, like in GoodFellas, but also for his comedic skills like in Home Alone.
The decision against Stiller may have had a different background than he thought
Instead of advancing his career with My Cousin Winnie, Stiller had to make ends meet in the 90s with supporting roles in films like Happy Gilmore and Cable Guy.
It is not known how Stiller did his audition in his opinion, screwed upbut the role that Stiller should have gotten. Rolling Stone published an article about the film in 2022 and conducted an interview with some of those involved. Including Ralph Macchio and Mitchell Whitfield, who played Winnie’s two nephews.
According to their statements, their roles were originally supposed to be played by Stiller and Will Smith. In the interview it was the decision against Smith and Stiller due to the theme of the film:
It really developed into an honest conversation about how the dynamic of the narrative would be changed by a young black man being wrongfully arrested in the Deep South.
The same was true for Ben Stiller:
This also applied to Ben Stiller. A young Jew in the South, suddenly you change the perspective of the film, especially at that time.
So Ben Stiller didn’t necessarily screw up his audition, but rather the casting director simply had concerns about the story. Whether you think that’s justified or not, it seems like Stiller didn’t have the slightest chance anyway.