Jim Carrey missed movie roles over the course of his career, but the casting decision that might have changed everything involved Matt Damon in a story of Hollywood’s shifting fortunes. In the late 1990s, the chance to lead a major project slipped away from Carrey, ultimately launching Damon into a new level of stardom.
How Jim Carrey Nearly Landed the Lead in “The Talented Mr. Ripley”
Jim Carrey and Matt Damon, two actors with contrasting styles and separate career paths, have occasionally found their professional lives nearly intersecting despite having never shared the screen. One such “ships in the night” moment came during the casting for a highly anticipated adaptation of Patricia Highsmith’s thriller, “The Talented Mr. Ripley.”
Before this, Carrey did secure a leading role in Frank Darabont’s “The Majestic.” While Carrey took the part of Peter Appleton, it was Damon who was first offered the role. Damon declined, a decision he would later appreciate as the film underperformed at the box office and was met with little enthusiasm from critics. Damon, however, still made a brief vocal cameo in the film.
At this point in his career, Carrey was purposefully stepping away from his comedic roots, trying his hand at more dramatic roles. While his performance in “The Truman Show” remains a celebrated pivot, other efforts, like “The Majestic” and “Man on the Moon,” did not generate the same acclaim. His ambition to evolve his on-screen persona led him to set his sights on the complex character of Tom Ripley.

Producers and Their Changing Choices
As Anthony Minghella worked to develop the screenplay for “The Talented Mr. Ripley,” he first considered securing Leonardo DiCaprio for the title role, fresh from the success of “Titanic.” However, with DiCaprio declining the offer, the producers resumed their search for a leading man. Jim Carrey lobbied energetically for the part, hoping to land this transformative role. According to producer William Horberg, Carrey’s enthusiasm was evident, but discussions ultimately did not progress.
The film’s production did not find clear direction until Harvey Weinstein got involved, using his influence in the industry to steer the choices. Weinstein brought in Matt Damon, having seen his work in “Good Will Hunting,” and also recruited Gwyneth Paltrow, who was set to star in “Shakespeare in Love.” With this casting, the lead role became an opportunity for Damon to showcase his depth as an actor.
Matt Damon’s Path to Acclaim
The opportunity in “The Talented Mr. Ripley” came at an ideal time for Damon, following his Oscar-winning success as a screenwriter for “Good Will Hunting.”
“a script that I like, a good director, and a good role,”
Damon explained—screenwriter.
He continued, saying he could usually,
“settle for any two of those.”
—screenwriter.
But with this project, Damon noted that,
“all three is really hard to come by.”
—screenwriter.
The role allowed Damon to prove that his earlier achievements were not a one-time occurrence. His performance as Tom Ripley stands as one of his most acclaimed, giving him the room to develop as a leading man in Hollywood. It was a powerful confirmation of his potential in dramatic roles, and remains a personal favorite among his many performances.
What Jim Carrey Did Next
While Jim Carrey did not secure the Ripley role, he did not let it derail his ambitions. Instead, he delivered a stand-out performance in “The Truman Show” in 1998, earning a Golden Globe for Best Actor in a Drama. Although many felt he was overlooked by the Oscars that year, Carrey’s commitment to challenging parts helped shape how audiences perceived him, extending his career beyond comedy and reinforcing his drive as an actor willing to face creative risks.
The story of how Jim Carrey missed out on “The Talented Mr. Ripley” illustrates how quickly the entertainment landscape can shift, as well as how one casting decision can shape not only individual careers but also the direction of cinematic storytelling. The film brought Matt Damon acclaim and new opportunities, while Carrey’s journey proved that missed roles sometimes pave the way for different, equally memorable milestones.

