Matt Damon Reveals the Hollywood Legend He Aspires To

Matt Damon’s journey through the world of film has been anything but ordinary. From his Oscar-winning breakthrough in Good Will Hunting to a string of acclaimed roles and collaborations with top-tier directors, Damon has carved out a place for himself that most in the industry would envy. Yet, for all his achievements, he’s the first to acknowledge that some figures in the business simply operate on a different plane.

While plenty of actors have tried their hand at directing, few have managed to excel in both arenas quite like Clint Eastwood. Eastwood’s name has become something of a yardstick for those hoping to leave a lasting mark, not just in front of the camera but behind it as well. The likes of George Clooney, Ben Affleck, Mel Gibson, Warren Beatty, Kenneth Branagh, Kevin Costner, Sean Penn, and Woody Allen have all earned their share of accolades, sometimes even Oscars, for their work on both sides of the lens. Still, Eastwood’s ability to become a legend twice over—first as a star, then as a filmmaker—puts him in a league of his own.

Before he ever directed a single frame, Eastwood was already a household name. His directorial debut with Play Misty for Me in 1971 marked the start of a parallel career that would see him juggle leading roles and directorial duties with apparent ease. Though he never took home an Oscar for acting, he’s collected four for his work as a director and producer, and he’s shown no sign of slowing down, even as he’s entered his tenth decade.

Eastwood’s Enduring Influence

Unlike his long-time friend and Good Will Hunting co-writer Ben Affleck, Damon has never felt the urge to step behind the camera himself. He’s content to write and produce, but directing doesn’t seem to be on his agenda. That hasn’t stopped him from looking up to Eastwood, especially after working with him on Invictus and Hereafter in quick succession. Reflecting on their time together, Damon shared just how much he valued the experience, saying he “learned something every day with him.”

“It’s just his philosophy on work and how he’s managed to be different all the time,” Damon said. “It’s the mark of true artist to defy any categorization for six decades in the movie business. To bathe in the glory of that example is a good reason to want to work with him.”

For Damon, Eastwood’s approach to his craft and his refusal to be pigeonholed are what truly set him apart. The chance to observe that up close was, in Damon’s words, a privilege in itself.

The Benchmark for a Lasting Career

Though Damon may not have ambitions to direct, he’s well aware that two of his closest mates—Affleck and Clooney—do, and they share his admiration for Eastwood’s career. As Damon put it,

“He is the goal. He is the one who my friends talk about when they talk about where they want to be. Ben and Clooney; Clint has the career they want.”

There’s a certain aspiration among this group to keep working at a high level for decades to come, just as Eastwood has done. Damon notes that the trio “want to believe we can do this at a high level for another four decades,” and Eastwood’s ongoing success makes that dream seem just a bit more attainable.

Longevity Few Can Match

It’s a tall order, of course. Not many in the history of the industry have managed to remain relevant for over seventy years. Still, Damon’s own career—spanning more than twenty-five years as a sought-after talent—suggests he’s making a fair go of it. The bar set by Eastwood may be sky-high, but for Damon and his peers, it’s a challenge worth pursuing.