The greatest co-star Matt Damon ever worked with: “I’m not being hyperbolic when I say this”
From day one, Matt Damon never took anything for granted in his Hollywood career. Ever since working on his first student films with friends like Ben Affleck, Damon knew that he could do anything he set his mind to as long as he believed in it, ultimately having one of the most impressive careers in modern cinema. Although Damon may have many classics to his name, one of the lower lights of his catalogue brought him face-to-face with one of his favourite actors.
In the early days, though, Damon was known for working with any script that struck a nerve with him. Although he would collaborate with fellow rising stars like Brendan Fraser on movies like School Ties, his greatest strength came when he worked with Affleck to get Good Will Hunting off the ground. After delivering a powerhouse performance alongside Robin Williams, Damon’s life changed dramatically, eventually working with craftsmen like Steven Spielberg on movies like Saving Private Ryan.
Around the turn of the century, though, Damon’s star had begun to wane slightly. Outside of the dramas he loved starring in so much, his career was brought back to life when he worked on The Bourne Identity, playing the titular cold-blooded assassin as he tried to come to grips with who he was.
After regaining his footing again, Damon decided to branch out into more off-the-wall projects, leading to him working in the movie The Brothers Grimm. Based on the historical figures, the Terry Gilliam film ended up being a stopgap between the filming of the Bourne franchise for Damon until he came face-to-face with Heath Ledger.
At the time, known for his work in movies like Brokeback Mountain, Ledger was starting to craft himself into a true movie star, inhabiting every role with a certain amount of gravitas whenever he stepped behind the camera. While The Brothers Grimm didn’t meet the exact sales expectations that most people expected, Ledger was on the verge of something even more significant on the horizon.
In the next three years, Ledger would turn in two brilliant performances before his tragic passing, creating a brilliant fictitious portrait of Bob Dylan in I’m Not There and exploring the mind of Batman’s greatest foe, the Joker, in The Dark Knight. When talking about his experience working with Ledger, though, Damon would say that his star power far outshone any other actor he had worked with.
Looking back on his time working on the film, Damon recalled just how well Ledger could infuse his spirit into his roles, saying, “It was great [working with him]. I’m not being hyperbolic when I say this, but he is the best actor that I have ever worked with. [His death] isn’t something that I will ever get over. He was a really special guy whose light was just too bright for this place”.
Then again, what Damon saw may have been only a fleeting glimpse of what Ledger was capable of. Although he may not have lived to see his career flourish, any one of Ledger’s roles is an excellent example of seeing a film legend in the making.
For Damon, who had already shared scenes with titans like Robin Williams and worked under directors at the very top of their craft, that is no small statement. It speaks to something intangible in Ledger’s presence, a fearlessness and immersion that elevated even uneven material. On a film that may not rank among Damon’s proudest achievements, he still found himself witnessing artistry at its most instinctive.
In retrospect, The Brothers Grimm feels less like a footnote in Damon’s career and more like a quiet crossroads moment. It paired a seasoned rising star with another who was about to redefine his generation. Ledger’s time was tragically short, but the impression he left on peers like Damon confirms what audiences would soon come to realise. He was not just promising. He was extraordinary.
