Would The Top Matt Damon Movies Be Better As DiCaprio Movies?

In May we hypothesized that the top box office hits for Leo DiCaprio would be better if they starred Matt Damon. This all came off the back of The Sports Guy, Bill Simmons, comment that ''I believe every DiCaprio movie would be just a little better as a Matt Damon movie.''. At the time we ended up with a 5-5 tie between the two great actors but noted that;

In summary, does this 5-5 tie come anywhere close to proving Simmons’ somewhat outrageous comment? Not really, no. Not really, for two reasons. First, Damon only barely got the nod for most of his 5 wins. DiCaprio absolutely annihilated the suggestion with most of his 5 wins. For example, going back to The Wolf, there’s no way Damon improves on that performance, in any imaginary scenario possible. So, the 5-5 tie is at best a precarious position for Damon. The second reason? Simmons’ original hypothesis can only be fully fleshed out be visiting the same topic upon Damon’s movies. Could DiCaprio have made Damon’s top 10 movies ‘better’?

Well guess what, it's time to find out. It's time to put DiCaprio in ten of the most famous Matt Damon roles and ask, would Leo have done a better job than Matt?


10. Rounders.

Rounders shouldn't technically be on this list. It sits currently at joint 32nd on Matt Damon's all-time box office list. The fact is however, despite its slow start at the box office, Rounders has become a cult classic and an essential Matt Damon classic. That out of the way, would DiCaprio in the Damon role improve Rounders? Well, it would definitely have been a different movie. Better? There is a goofy likeability at the heart of Rounders. Whether it's the fun, quasi sleazy, late-night-drinks soundtrack, Edward Norton's boisterous 'Worm' or John Malkovich's over the top Teddy KGB, Rounders might not be technically the greatest movie of all time, but it's a very, very likeable movie. Adding DiCaprio, instead of Damon, might have brought a level of seriousness and perhaps a depth, but that wouldn't have fitted in the context in which Rounders works. So, no, Rounders would not have been better had DiCaprio played Damon's role.

Matt Damon 1-0.

9. The Talented Mr. Ripley.
Ripley did surprisingly well at the box office, taking in almost $90 million, which back in the 90s was decent. It's a terrific, well paced and stylish movie, and, perfectly cast with Damon in the lead role. I say that last part with authority primarily due to one line, delivered early on as Damon meets Law on the beach for the first time. ''Dickie Greenleaf? It's Tom, Tom Ripley, we were at Princeton together.'' Here's the thing, if that's DiCaprio, and he's standing there delivering that line, you just know, immediately, that something is afoot. The audience knows, Dickie Greenleaf knows, we all know immediately that something is not right and this dude is up to something, for sure. With Damon's Ripley, you don't know. He's too goofy in those little yellow shorts and with that foppish hair, way too goofy, to be up to anything, surely? Damon's early innocence and goof lends itself perfectly to the Ripley character. Pushing DiCaprio into that role might have brought some extra menace, but at the cost of the innocence and believability of the Damon Ripley, so essential to the story.

Matt Damon 2-0.

8. Elysium.
At the heart of this exercise we're not judging a movie, we're judging whether one certain actor would do better if they replaced another in said movie. In this case, with Elysium, it's hard to argue DiCaprio wouldn't add a certain grit and tenacity to the Damon role. For whatever reason, Damon is oddly not given much humor, physical or verbal, to work with in Elysium, and that's kind of the point in bringing Damon into a role like this, see The Martian for a perfect example. In this role, with this script, in this movie, DiCaprio could do the robotic with aplomb, and might bring a little extra to the table while doing so.

Matt Damon 2-1.

7. The Departed.
When writing the flip side of this, putting Damon in the DiCaprio role, it was pretty clear that would work, and it's easy to recycle that sentiment and use it here. Damon would be great in the Billy Costigan role, and would bring a different kind of fresh vulnerability to it. On the flip side, DiCaprio would have made an excellent Colin Sullivan, and as we said previously, would have brought some serious extra menace to the role. I hate double guessing casting, particularly in a movie that's so good and which I enjoyed so much, but in this case, you have to suggest The Departed would have been even better had they flipped the lead roles.

We're at a tie, 2-2.

6. Good Will Hunting.
The temptation here is to say, 'No, nope, not even close.' However, you have to imagine DiCaprio in '97 to accurately asses if he could fill out this character better than Damon, and subsequently create a better movie. You think about that, and, you start thinking, 'well, maybe'. However, Good Will Hunting is built primarily on a couple of relationships, and in both of those, Damon excels. The movie succeeds not on the basis of this awful, awful trailer, not on the basis of the tongue in cheek humor or the love interest story line (at times pretty kitsch), but instead it succeeds on the interplay between Damon and Affleck and Damon and Williams. In both situations, Damon is superb. While DiCaprio might have done a fine job overall, Damon created something special in his relationships with Affleck and Williams. That almost father and son like bond that developed in front of us between Damon and Williams is a thing of beauty, and very hard, if not impossible, to recreate.

Matt Damon takes the lead again 3-2.

5. True Grit.
Grit is an unexpected gem. Jeff Bridges hammers home his credentials as an American Treasure, a truly brilliant performance, I'm going to go as far as saying the greatest modern Western performance to date. Damon's LaBoef flits in and out of the story at important junctures and provides some levity and a nice balance to Bridge's Rooster Cogburn. Introducing DiCaprio into this role could have upended that balance and changed the dynamic of the movie. Damon was understated, and I don't know if DiCaprio can do that, understated.

Matt Damon 4-2.

4. The Ocean's movies (all of them).
Bunching the Ocean's movies together makes sense as Damon plays the same character all the way through and those character traits solidify as he goes through the sequels. Damon brings his usual, affable, everyman goofiness to the role and by the time we get to the third part of the story, the movie is leaning heavily on Damon and sometimes squirmingly awkward situations. The fake nose thing for example, simply no way DiCaprio pulls that off without someone physically pointing a gun at him, or threating to melt a glacier or something. Damon's Ocean turn works because it's Damon, and because of his relationship to Clooney and Pitt. Stick DiCaprio and his somewhat lone-wolf persona in that mix and, who knows what you'd get. Whatever happens, no way you get him to do that nose gag. Just no way.

Matt Damon 5-2.
3. Saving Private Ryan.
A short but pivotal role, there's a certain vulnerability required to play Private Ryan. His scenes all involve Damon playing an Iowa farm boy type, complete with goofy laugh and a level of soft sentiment that not many could bring to that role. DiCaprio would have brought a steel and an edge, sure, but it might have been out of place here. Perhaps the easiest one to judge, no way DiCaprio improves upon the movie with his inclusion.

Matt Damon 6-2.

2. Bourne (All of them!).
Now we're getting to the good stuff. Let's ask it out loud, would the first three Bourne movies be 'better' with DiCaprio in the lead role? Thinking about what DiCaprio would have brought to the role, there definitely would have been an uptick in urgency and tension. DiCaprio walking swiftly down a Swiss street, or DiCaprio beating bad guys up in Waterloo station might have been edgier and somewhat tougher than the Damon version of same, but, it's not these scenes that set the tone for the opening Bourne trilogy. Instead, think of the elements that made Jason Bourne what he is. Think of Bourne waking up on a park bench in the snow, and discovering he could kick the crap out of Swiss Police officers. Think of Bourne and Marie outside the hotel, ad-libbing their way into a plan to obtain phone records (so simple, so human, so effective), Damon delivers a brilliant 'Oh, ok' moment when Marie gets the job done, I don't see DiCaprio getting that moment right. Think of Bourne in any of the more innocuous situations and it's hard to imagine DiCaprio duplicating the humanity in those parts. I contend it's those background building moments that make Bourne the success it is.

Matt Damon 7-2.

1. The Martian.
Good golly The Martian was a massive success. Over $230 million gross, $54 million on its opening weekend alone. They couldn't have thought it would be this successful. Sometimes a good movie just happens, kind of out of the blue. A large slice of that success is of course Damon's every-man, delivered so easily, with just the right level of humor at the right time. Damon is laugh-out-loud funny in several parts, and brings a great humanity to the role. I think we can all see where this is going.

Matt Damon wins, with a stunning, landslide 8-2 win over DiCaprio. The simple truth is that, no, the top Matt Damon movies would not be better with DiCaprio in the leading role. This doesn't mean either actor is necessarily 'better' than the other. In this case it just means that I believe Damon was very well cast in his top movies.
When we looked at the reverse a couple of months ago, we decided that a 5-5 tie was apt for the top 10 DiCaprio movies. This suggests Damon might be a slightly more flexible actor than DiCaprio, but remember the caveat, in the 5 that DiCaprio won, I suggested he won handily, easily proving the better cast actor in those cases.

What have we learnt? DiCaprio is well cast in over half of his movies, Damon perhaps even better cast in the majority of his. DiCaprio brings a seriousness, depth and edge to his roles, while Damon's everyman act is used to perfection in his top movies. Most of all, that's twenty seriously good movies and movie sets we're talking about, and the common denominators are Damon and DiCaprio.

Maybe that's all we need to know.