It’s a sign you’ve made it in Hollywood when the roles you’ve been offered are just as prestigious as the roles you’ve accepted.Matt Damon– one of his era’s most bankable stars – is a stellar example. The Golden Globe-winning actor infamouslyturned down Jake Skully inJames Cameron’sAvatar, losing him an estimated $250 million paycheck in the process (“It’s the dumbest thing an actor ever did in the history of acting,”he later joked), but this is only one time when Damon’s career almost took a sharp 90-degree turn. When factoring in such possibilities asBrokeback Mountain,Training Day, andStar Trek(to name but a small selection) it’s not inconceivable to suggest that Damon could have built an entirely divergent filmography for himself and still obtained his A-list status. Quite an accomplishment indeed.
But of all the incredible movies that Damonjustmissed out on, there’s one that provokes the most interest in aWhat If…?style excursion into the realm of speculation – none other than a leading role in the undisputed king of superhero films,The Dark Knight.WhenChristopher Nolanwas castingfor his most influential (and perhaps greatest) directorial work, Damon was one of many actors he considered for the part of Harvey Dent, Gotham City’s righteous district attorney who gradually transforms into the revenge-fueled tyrant Two-Face.

The Dark Knight
When the menace known as the Joker wreaks havoc and chaos on the people of Gotham, Batman must accept one of the greatest psychological and physical tests of his ability to fight injustice.
Harvey Dent Is ‘The Dark Knight’s Most Important Character
It’s easy to forget how important Harvey Dent is toThe Dark Knight. Of course, anyone who has to compete for screentime withHeath Ledger’s stunning tour de force performance as the Joker – arguably the greatest feat of acting in the history of superhero movies – will struggle to obtain the spotlight, but Dent plays such an integral role in the story there’s a case for him being the film’s secret main character. At its core,The Dark Knightis about a strugglebetween Batman (Christian Bale) and the Joker for the fate of Harvey Dent, with each having placed an idealistic goal on the district attorney that represents their preferred vision for Gotham.
When we first encounter Dent during the trial for one of mob boss Sal Maroni’s (Eric Roberts) associates, he embodies everything that Batman wishes he could be: a glowing beacon of justice who operates entirely within the law. He’s the legitimate hero Gotham deserves, and it’sno surprise that Batman comes to view himnot just as an ally, but also as a potential successor. Harvey Dent is a savior who seems too good to be true, and as comic fans will already know, that’s more accurate than any of his passionate supporters would like to admit.

Given how important Harvey Dent is toThe Dark Knight(practically every theme the film explores is intricately linked to his character’s moral collapse), choosing an actor to play him was never going to be easy. Not only would they have to modernize the classic all-American hero archetype for the digital age, but they would also have to imbue their performance with undercurrents of suppressed anger that would gradually envelop him as the film progressed. The combination ofJohn F. Kennedycharisma with Norman Bates; the-evil-next-door subterfuge would be difficult for any actor to believably portray (especially when you’re missing half of your face) but thankfully Nolan had just the person in mind.
Scheduling Conflicts Prevented Matt Damon From ‘The Dark Knight’
Conceptually,Matt Damon was the ideal choice for Harvey Dent. His screen persona as a handsome tough guy with enough charm to inflate a helium balloon was practically designed for an aspiring politician who could convince anyone to vote for him with only a smile and a well-placed slogan, and it would also make for some friendly rivalry between him and Christian Bale as they competed to be Gotham’s most desirable bachelor. However, Damon has also proven himself to be one of Hollywood’s mostidiosyncratic and at times underrated stars– frequently taking roles deflecting the criticisms aimed at many A-list stars that they’re essentially just playing themselves.Even Jason Bourne, Damon’s most recognizable role, lacks the allure of similar spy icons like James Bond and Ethan Hunt, but deliberately so. He’s a nebulous character whose as much a mystery to himself as he is to everyone else, but also someone who’s not afraid to get his hands dirty if the situation calls for it… much like another role that was coming Damon’s way.
There Was a Good Reason Heath Ledger’s Joker in ‘The Dark Knight’ Was Licking His Lips
Why so serious?
Sadly, it wasn’t meant to be. The age-old problem of scheduling conflicts prevented his involvement inThe Dark Knight, with Damon having already committed to headlining another project. Given that the opportunity to lead a major Hollywood production is one that most actors never come within reach of, and Dent was – to quote Damon –a “relatively small” part in a filmthat no one suspected would become a cultural behemoth, it’s forgivable that he would turn it down in favor of the role he perceived as more significant. That said, it’s curious that he would refer to Dent using those terms.

Batman and the Joker may have far and away the most screentime inThe Dark Knight, but Dent is unequivocally the backbone of the entire narrative (even the title refers more to Dent than it does to Batman) – but his decision was final, prompting Nolan to castAaron Eckhartinstead. Damon has insisted that he has no regrets over what happened, stating inan interview with MTVthat Eckhart is “a great actor” who benefitted the film immensely. That may be true, but it’s hard to think that part of him didn’t feel a bang of remorse whenThe Dark Knight’s box office numbers came rushing in.
Matt Damon Worked With Christopher Nolan in ‘Interstellar’ & ‘Oppenheimer’
The release ofThe Dark Knightin July 2008 was nothing short of a revolution. Overnight, expectations of what a superhero film could be were shattered by one of the most impeccably crafted films in years, proving that even a story about a billionaire who dresses as a bat could describe itself as prestige cinema. The film cemented its winning streak months later when it became the first superhero movie to earn major recognition during the end-of-year awards season, and it wouldn’t take long for the slew of dark, gritty imitators to follow in its wake (for better or for worse). Today,it is regarded as one of the most influential films ever made, and while the central reason for its longevity is often placed squarely at the feet of Ledger’s Joker, the truth is far more complex.The Dark Knighthas an ensemble cast for a reason, but it’s Harvey Dent who stands as its greatest asset. His downfall from honorable prospector to deranged killer is the glue that holds the entirety ofThe Dark Knighttogether, andEckhart deserves immense praisefor his contributions in turning this once silly character into one of the most thematically compelling villains in the Batman mythos.
But how different things could have been! We’ll never know how Damon would have performed in the role, and getting lost in the labyrinth of guesswork is a path to madness, but we can infer that – despite his earlier comments to the contrary – part of him regretted turning it down.No doubt this factored into his enthusiasm at accepting an even smaller role in Nolan’s sci-fi epicInterstellar– a part so minute it was left out of the marketing campaign to avoid misleading audiences about his screentime (although, as with Harvey Dent, it’s an important role in the overarching plot). “I wanted to be part of that troupe,” as he confirmed years later, adding that “[Nolan] works with the same actors over and over again [and] I wanted to be on that ride.” Well, thanks to a pivotal role asGeneral Leslie Groves inOppenheimer, he has finally achieved his wish, with recent interviews indicating that he eagerly awaits their next collaboration. Better late than never, but withThe Dark Knightstill popularly considered Nolan’s best film, it’s safe to say that he’s still a little upset at having waited so long.

The Dark Knightis available to watch on Max in the U.S.
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