The iconic career Matt Damon wants to emulate: “I feel like I’m ready to do it”
Every actor has dreams of a long and storied career in the industry, and Matt Damon is no different. It’s a good dream, and one that some could argue that Damon achieved, after all if anyone can force a dream, he can. He shot to fame when he and Ben Affleck co-wrote and co-starred in the 1997 drama Good Will Hunting and has gone on to establish himself as a solid but perhaps unremarkable leading man.
He is most well known for his work on the Bourne Trilogy, playing amnesiac CIA agent Jason Bourne, a condition I wish I’d developed after seeing Jeremy Renner’s fourth instalment in the saga, The Bourne Legacy.
In an interview from 2007, Damon names two actors who he hopes to emulate, “Well, [George] Clooney’s definitely doing it right now, and Clint Eastwood. Those are the careers where they’re acting, they’re writing, they’re directing, and they’re doing it on their terms.” It’s no shock that Matt names both Clooney and Eastwood specifically. He’s been fortunate enough to work with both.
Damon famously stars alongside Clooney in the Ocean’s Trilogy, a remake of the original Rat Pack heist film. Alongside acting together, Clooney also directed Damon in the 2017 black comedy Suburbicon. However, Damon’s collaboration with Eastwood is limited to just one project, Hereafter, a fantasy disaster film that Eastwood directed.
As far as career trajectories go, Clooney and Eastwood are not bad role models by any stretch. Clooney got his start acting on NBC TV drama ER, and from there, he built a career in film, rising to real stardom as the lead in Steven Soderbergh’s Ocean’s trilogy alongside Damon. His efforts haven’t gone unrewarded, with Clooney winning the Academy Award for ‘Best Supporting Actor’ in Syriano and two nominations for ‘Best Actor’ for his roles in Michael Clayton and Up In The Air. Alongside his acting success, Clooney has directed six feature films, and won the Academy Award for ‘Best Picture’ for co-producing Argo.
Besides Eastwood, even Clooney pales in comparison, with a career stretching over 70 years. Getting his start in the TV Western Rawhide, he rose to prominence in Sergio Leone’s Dollars Trilogy, easily the most iconic ‘Spaghetti westerns’ ever made. Eastwood went on to star in over 60 films, twice being nominated for ‘Best Actor’. Alongside his acting career Eastwood has also directed over 40 films, winning five Academy Awards.
Eastwood is notorious for his efficient directing style, forgoing the likes of rehearsals and re-shooting takes to speed up production. His directorial impatience even led to a bust-up with director Philip Kaufman on the set of The Outlaw Josey Wells, with Eastwood having Kaufman fired and taking the director’s chair for himself. An act that caused outrage at the Director’s Guild of America, which has since created the ‘Eastwood Rule’ banning this practice.
Damon has appeared in 41 films as an actor and produced over 20, but compared to Eastwoood, these are still rookie numbers. At the time of the interview, Damon remarked on the longevity of his career so far, “I mean, it’s so hard to have a long career in this business. I mean, I’m still here after ten years, and we’re all probably a little amazed by that“. In 2025 he’s been active in the industry for 28 years, and I’d like to think we’re all probably still a little amazed by that.
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