Leonardo DiCaprio and Matt Damon Almost Reunited 3 Years After The Departed for A True Masterpiece

Discover why Leonardo DiCaprio and Matt Damon never joined this superhero movie and why fans crave their cinematic reunion.

leonardo dicaprio and matt damon in the departed
Credits: Plan B Entertainment.

In The Departed, we got a glimpse of cinematic magic when Leonardo DiCaprio and Matt Damon shared the screen under Martin Scorsese’s direction in 2006.

But Hollywood almost gave us even more because the two were nearly reunited for another high-profile project: The Dark Knight. 

Christopher Nolan’s saga became a landmark in superhero films, and the prospect of seeing Damon and DiCaprio in it remains one of the most tempting “what-ifs” of the entertainment industry.

So, let’s look at how the duo almost starred in The Dark Knight, followed by why there needs to be a movie that reunites them.

Why Leonardo DiCaprio and Matt Damon Never Crossed Paths in The Dark Knight

Matt Damon talking on a flip cell phone in The Departed.

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Leonardo DiCaprio wearing a suit and tie in The Departed.

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Matt Damon wearing a blue uniform in The Departed.

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Leonardo DiCaprio wearing a suit and tie in The Departed.

According to David S.Goyer, who is the co-architect of Christopher Nolan’s trilogy and was the head of Warner Bros., the former revealed on the Happy Sad Confused podcast that he had personally suggested placing Leonardo DiCaprio for the role of the Riddler in The Dark Knight Rises.

But then the idea of the character being in the movies was completely tossed out the window.

You got to do the Riddler.

Leo as the Riddler.

You got to tell Chris, Leo as the riddler.’ And that’s not the way we work.

Matt Damon himself confirmed on the Happy Sad Confused podcast that he was offered the role of Harvey Dent, aka Two-Face, in The Dark Knight; however, he passed the offer (via The Playlist).

In the same conversation, he also expressed regret over turning down Avatar, like he’s done a million times before.

Matt Damon and Leonardo DiCaprio’s The Departed Chemistry Demands Reunion 

Leonardo DiCaprio and Matt Damon in an elevator in The Departed.
Matt Damon and Leonardo DiCaprio | Credits: Plan B Entertainment.

Even without being a part of Gotham’s chaos, the chemistry that we saw between Leonardo DiCaprio and Matt Damon in The Departed is undeniable. Their portrayal of Costigan and Sullivan is a masterclass in how you showcase parallel tension.

Here’s an overview of the feature:

Title
The Departed

Genre
Crime Thriller

Director
Martin Scorsese

Cast Highlights
Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg

Rotten Tomatoes
(critic score | audience score)
91% | 94%

Throughout the film, they’re in a psychological cat-and-mouse chase, and as the viewers, we’re on the edge of our seats at all times.

The brilliance of their interactions lies in the subtle way they interact with the story, not necessarily with each other.

The two create a contrast and an invisible thread that binds The Departed together, and reuniting these two actors could potentially recreate that same magic.

Imagine the two in a modern thriller or even a new Christopher Nolan or Martin Scorsese movie!

Would you tune in to watch if the two were to show up together?

You can watch The Dark Knight trilogy on HBO Max and The Departed on Netflix (USA).