I’m sure I’m not alone in believing that Matt Damon is one of the most naturally likable on-screen presences of his generation. It’s also not controversial in the slightest to say he’s a hugely talented actor.
Therefore, I’m always fascinated by roles he takes on where he’s either a flat-out “bad guy” or has some morally gray component that effectively clashes with his innate charm and earnest energy.
The worst baddies of them all
For my money, the most vile character that Damon has ever taken on is a very early role in School Ties from 1992. The part is pretty small, but as boarding school kid Charlie Dillon, Damon effectively radiates hatred and bigotry when Brendan Fraser’s David Greene is found out to be Jewish in this 1950s-set coming of age story.
What’s ironic here is that as much as the “real” Matt Damon exudes integrity and level-headed intelligence, Charlie Dillon embodies closed-minded privilege and prejudice.
Damon’s turn as Colin Sullivan in The Departed (2006) is arguably the most evil major character he’s played to date. What’s deliciously evil about Sullivan is that he’s self-aware enough to know how vile he – a dirty cop completely under the thumb of the Boston mob – even as the stakes visibly eat away at him.
The dynamic versus Leonardo DiCaprio’s haunted, doomed undercover cop William Costigan, Jr. is spectacular, and together it helps to make The Departed one of Martin Scorsese’s most effective crime dramas (setting aside Jack Nicholson’s unfortunately looney performance as mob boss Frank Costello).
Sidenote that I’d love to see Damon and Scorsese team up again before the legendary director retires.
Still pretty baddie characters who want to believe they’re doing the right thing
The Talented Mr. Ripley (1999) is one of my favorite movies, and Damon’s performance as Tom Ripley is a big reason why. This version of Ripley is not all that self-aware and is seeking out love, really… it just happens to be in all the wrong places.
And then there’s the part where he does tend to snap from time to time.
I must also add that I am astonished at how good Ripley, the more recent Netflix limited series adaptation is while taking a drastically different route to telling the same story.
See where Ripley dropped in on the recently updated best 100 TV shows ever.
There are many who revere Interstellar (2014), but I have very mixed feelings about it myself. That being said, I very much perked up when Matt Damon’s Mann pops up fairly late in the proceedings.
What plays nicely here is that Mann’s rescue in the deep reaches of space (and time) is seemingly set up as part of third act momentum to an eventual happy ending, but the rug is soon pulled out from under us when Mann and Matthew McConaughey’s Cooper go out for a little walk.
Damon’s Ripley and Mann are self-centered people who act cruelly when it suits them, which makes each of them compelling.
Just kinda bad in a not really fun or interesting way
The Last Duel (2021). Let’s just leave it there.
Are they the goodies or…?
Over the years, Damon became adept at playing against his earnestness where you’re not sure if his characters’ intentions are noble or not.
Seeing Damon’s latest flick, The Rip (which turns out knows it’s a movie, in fact), inspired me to write this piece as much of the plot hinges on whether his Lieutenant Dane Dumars has the best intentions for his team and the law – and we don’t find out the answer until the very end (I’ll just note that there’s a fun and effective twist involved en route).
The Robert De Niro-directed The Good Shepherd (2006) is an underrated movie that doesn’t get mentioned very often these days. Damon plays a buttoned-down CIA lifer named Edward Wilson who, by film’s end, knows where the bodies are buried. He’s literally The Company Man.
The performance is enigmatic, and makes us consider the dark places that our intelligence services play into keeping us safe – assuming intentions are above board.
You could argue they’re bad guys, but come on
Let’s put the Ocean’s movies into this category, ripping off casinos and such, and throw in Rounders (1998) – Damon’s Mike and Ed Norton’s Worm taking money off poor saps in poker – for good measure.
But within the contexts of these movies and fictional worlds, they’re clearly part of Team Good Guys. These are rollercoaster ride movies, and we want to see our guy enjoying cotton candy and popcorn by the time the final credits roll.