I wanted to challenge myself. I can’t think of an easier way than attempting to narrow down the top five roles in Matt Damon’s long and illustrious career. Of course, with a post like this, there will be much up for debate. This is just the opinion of one man, so don’t tar and feather me when I don’t include Stuck on You as an example of Damon’s best work.

Before I jump into Damon’s best roles, I’d like to highlight one of his most important roles, his narration of the 2009 Academy Award winning documentary Inside Job. The film profiles our country’s financial woes in regards to the housing bubble. Even if you don’t understand economics or dense financial material, this movie lays it all out and shows the criminals (literally, these financial sector fat cats are crooks) behind the housing bubble. Damon’s narration and the film’s perfected storytelling make it all understandable. I will warn you, learning how the collapse happened and how those responsible made away with millions of ‘fabricated’ dollars will leave you enraged. But seriously, Inside Job is a must see.

As I stated, these are his best roles, not the best movies he’s been in. This also gives an advantage to his work as Jason Bourne and Linus Caldwell as the audience got the opportunity to get to know this character through three films and not just one. But, let’s get started.

5. Linus Caldwell — Ocean’s 11, Ocean’s 12, & Ocean’s 13 

This is definitely the worst name Damon has ever had in a film — sorry to anyone reading named Linus. I love the Ocean’s Trilogy, Ocean’s 12 wasn’t as good as the bookends, and Matt Damon alongside Clooney and Pitt is a huge reason why. This trio, supported by the amazing surrounding cast, makes for three fun-filled movies with plenty of intrigue and desire to see the elaborate plans work out. Damon isn’t a driving force in these films like he is in his other prominent roles, but his presence always makes for a good time. “The nose plays.”

4. Colin Sullivan — The Departed

Like The Talented Mr. Ripley, it’s odd to see Damon playing the bad guy in a movie (spoiler!). He’s so likable it’s difficult to imagine him as a bad guy. However, Damon is such a great actor he can pull off ‘the rat’ in The Departed with ease. He plays both sides of the fence pretending to be a loyal cop and boyfriend as well as an insider for the notorious gangster played by Jack Nicholson. It’s brilliant to watch Damon’s cool bravado break down and the end of this film when his world is unraveling. “Just fucking kill me. Just fucking kill me.”

3. Jason Bourne – The Bourne Identity, The Bourne Supremacy, & The Bourne Ultimatum

How can you argue with this choice? Jason Bourne is an unstoppable force who is always at least twelve moves ahead of the opposition. He starts as an emotionless soldier, but learns to love after meeting the roaming gypsy Marie. Who would’ve thought that making a woman fall for you was as easy as escaping an entire police force in an insane car chase in an old red Mini Cooper through bustling traffic? Simple enough. I know after seeing that scene I was in love with Jason Bourne.

This series has some of my favorite cinematic moments of all-time — the sniper scope on the roof (pictured above) is one, the use of a pen and a rolled up magazine as weapons in gritty fight sequences are two others. There isn’t a second in any of these three movies where Damon doesn’t embody this character. “You move, you die.”

2. Mike McDermott — Rounders

Teaming up the talents of Damon and Edward Norton is sure to be a dynamite film right? Of course. Add in John Malkovich playing the Mad Russian, Teddy KGB, the movie has to be the stuff of legend right? Duh. Rounders is the biggest reason why I got into playing Texas Hold’em, a game I take very seriously even today. Damon is the friend Mike that doesn’t know how to say no to Norton’s character Worm. As the film progresses, Mike allows his life-long best friend to pile up the losses and dig the pair deeper into the dangerous world of illegal gambling. Sometimes, in order to save your own ass, you have to stop sticking your neck out for a troublesome friend.

Every time I watch this film, I cherish the chance to see Damon’s character Mike evolve from a seasoned card player, to a struggling law student, back to the expert card shark who is unstoppable on the felt. It’s hard to pick a favorite scene from Rounders, but they definitely all feature Damon.

One that comes to mind is when Mike gets advice from Martin Landau’s character, Judge Petrovkski. The pair is sitting down for a drink and the wise elder gives Mike this advice: “The last thing I took from the Yeshiva is this, we cannot run from who we are. Our destiny chooses us.” This moment inspires Mike to start rounding again, which sets him on a collision course with Teddy KGB, the man who wiped away his savings before. The final confrontation is so much more than memorable — it’s cinematic history. “Mr. Son-of-a-Bitch! Check! Check! Check! He tricked me!” “If you want Teddy, I can go on busting you up all night.”

1. Will Hunting — Good Will Hunting

I actually believe this is Damon’s best role and the best movie he’s in. This is one of my favorite movies of all-time and Matt Damon is a huge part of that (he also co-wrote the Oscar winning screenplay). Genius turned janitor? What a story right? Damon is magnificent as the immature genius Will who understands the world like so few but is unable to break free of dead end jobs, getting drunk with his friends, and wasting his brilliance. Damon’s portrayal is spot on and his interactions and relationships with the supporting cast is what makes this film soar.

Will works through his troubled past and insecurities with Robin Williams, hones his intelligence with Stellan Skarsgård, learns to appreciate his abilities with Ben Affleck, and learns to love with Minnie Driver. The chemistry between the growing couple Skylar and Will is apparent from square one — it’s one of my all-time favorite on-screen romances. Unlike most of the people in Will’s life, Driver’s character Skylar confronts him about his stagnant and underachieving life which climaxes into an eruption of emotion from both actors. Watching Will transform through his experiences with the people in his life is captivating each and every time. “I gotta see about a girl.”

Honorable Mentions:

I’ll throw out some honorable mentions. Saving Private Ryan is a WWII masterpiece, but Damon’s role in the film cannot hold water when compared to his work on the five roles listed above. The Talented Mr. Ripley is surely one of the most challenging roles of Damon’s career playing a merciless murdering sociopath. While I respect what he did to play that role and how well he portrayed it, neither Damon’s work nor the film itself ever struck a chord to make me want to re-watch it over and over.

Invictus is based on an extraordinary true story and has a lot to say about equality and humanity. I was sold on Damon’s character as the leader of the rugby squad, but his South African accent was pitchy throughout which always bothered me. Damon was great in The Good Shepherd, but it was easily one of the most boring and long winded films I’ve ever seen.

Lastly, I wanted to point out two roles where Damon is actually funny. His first was his brief cameo in Euro Trip where he plays a punk rocker named Donny who sings the infamous song, “Scotty Doesn’t Know.” I doubt that’s Matt Damon singing, but his physical appearance alone is almost unrecognizable. And for fans of Entourage, I’m sure you remember Damon playing himself as he tries to get Vince to donate big money to help his charity. Damon portrays himself as an absolute nut, stalking Vince down on the phone to which Drama replies, “Sorry, he Jason Bourne’d me.”

What Do You Think Of My List? Am I Off My Rocker? 

 

Follow Matthew on Twitter: @matthewdeery