The regret that still “haunts” Ben Stiller to this day

There was a time at the dawn of the 21st century when the cheeky chops of Ben Stiller found their way onto what felt like every DVD cover in Blockbuster. Indeed, the 2000s were a simpler time, one that had not yet been marred by the cynical influence of social media, though was certainly being swayed by its imminent arrival. Comedies were similar to that of modern cinema and television, with inherently silly plots and elaborate set pieces, helmed by a boys club led by actor and director Ben Stiller.

Rising to popularity in the late 1980s, Stiller found fame on Saturday Night Live as a writer and featured performer before creating the successful short film Elvis Stories which would earn him his very own slot on Fox Network with The Ben Stiller Show. However, Stiller was far more interested in directing drama and found his first taste of success in a leading role in the 1998 film There’s Something About Mary, a release that would catapult him to cultural prominence.

It certainly wasn’t plain sailing for Stiller, however, with the actor struggling through middling roles in the 1990s, taking minor roles in such films as Stella, Highway to Hell, as well as a cameo in The Nutt House. Constantly auditioning for multiple roles, Stiller laments the time that he missed out on a chance to appear in the celebrated 1992 movie, My Cousin Vinny, directed by Jonathan Lynn. 

20 years of ‘Zoolander’ Ben Stiller’s comedy gamechanger

Read More

Speaking at a Q&A about his latest directorial effort, Apple TV’s Severance, Stiller told the audience, “I tanked my audition for My Cousin Vinny. It still haunts me to this day,” revealing that he lost out on the chance to star beside Joe Pesci, Marisa Tomei and James Rebhorn in the ‘90s comedy classic.

Whilst Pesci was known as an intimidating villain on-screen when he wanted to be, starring in the classic Martin Scorsese crime movie Goodfellas, he was also a talented comedian, showing off a hilarious performance in My Cousin Vinny. For modern audiences, many will also recognise Pesci from Chris Columbus’ 1990 Christmas classic Home Alone, starring Macaulay Culkin and John Candy.

For Stiller, however, he missed out on appearing in My Cousin Vinny, a film that follows two New Yorkers accused of murder in rural Alabama who call on their loudmouth lawyer cousin with no trial experience for help. 

Instead of having the chance to appear alongside Pesci, Stiller struggled through the ‘90s, taking an uncredited role in Happy Gilmore with Adam Sandler and a supporting character in The Cable Guy with Jim Carrey as he skirted around a leading role in Hollywood comedy. After tinkering with his eccentric fashion designer character, who would become a cultural staple in 2001 upon the release of Zoolander, Stiller took a cameo role in Friends and eventually reached industry supremacy with There’s Something About Mary in 1998.

Related Topics