Okay, now we’re starting to get into the good stuff here. We will officially be entering into the Top Twenty films of Matt Damon’s career, and I don’t think there can be much argument about the quality of these films. Sure, there might be a handful in there that are more my speed than yours, but overall, these are just some really good movies. We don’t spend much time in any one point of his career, with release dates ranging from 1997 all the way up to 2023. We get more role diversity here as well: a 1950s lawyer, a knight in medieval France, a down-on-his-luck underground poker player, Jason Bourne, a cop from Boston (now re-read that last one in a Boston accent, please) and many more! Let’s take a look at the next chunk of movies in the rankings.
22. The Rainmaker
- Release date: November 21, 1997
- Budget: $40 million
- Box office: $45.9 million
- Letterboxd rating: 3.5 ★
- My Letterboxd rating: 3.5 ★
- Rotten Tomatoes: 82% (Certified Fresh ?)
Francis Ford Coppola delivers a solid late-career film with an all-star cast that is a great watch start to finish. While it may not be the best Grisham adaptation (depending on who you ask) and is certainly not anyone’s apex mountain, it is like an album you listen to from a band where you go “it’s not my favorite, nor is it their best, but I’ll keep coming back to listen to it and there’s some great singles on here.” The soundtrack felt fairly out of place for me, which was honestly the biggest detractor – most other nit picks come more from the story itself than the film, but it remains rewatchable nonetheless. Kudos to Damon and Voight for great performances here.
21. The Last Duel
- Release date: October 15, 2021
- Budget: $100 million
- Box office: $30.6 million
- Letterboxd rating: 3.7 ★
- My Letterboxd rating: 4.0 ★
- Rotten Tomatoes: 85% (Certified Fresh ?)
This movie was a bit confounding for me; there were aspects that I really enjoyed, and others that really missed the mark for me. I loved the cinematography, paired with the on-location set pieces – it was such a beautiful movie to watch and the color grading was spot on. The acting was superb, with Driver and Comer taking home the best performances of the film (honorable mention goes to Alex Lawther for his incredible portrayal of eighteen-year-old King Henry VI). The decision to split the story into three chapters, taking the point of view of the three main characters, was the best decision they could have made. It told the story in a refreshing and interesting way that kept my attention the whole time. The dialogue was the most confounding part of this movie to me – it was so bad! I was not expecting a movie co-written by Damon, Affleck and Holofcener to reek this poorly of terrible dialogue and some weird character choices. I also can’t decide if I love or hate Affleck’s performance/casting in this? He did a good job of making you love how much you hate his character, but I could not take him seriously in a fourteenth-century noble role. Overall, I think the movie was a success and I enjoyed watching it (even though the subject matter was no fun at all). It kinda felt like sitting down to see a $100 million play, so if that’s up your alley I say give it a watch!
20. The Informant!
- Release date: September 18, 2009
- Budget: $22 million
- Box office: $41.8 million
- Letterboxd rating: 3.3 ★
- My Letterboxd rating: 4.0 ★
- Rotten Tomatoes: 80% (Certified Fresh ?)
Soderbergh really went for it with this one, and it didn’t resonate with a lot of people for that reason. But I find this to be such a charming and funny satire of a pretty serious real-life situation with some top-tier acting from Damon. I think if you try telling this story in a different way, it loses the irony that saturates it so organically – it’s a story you tell someone and they respond with, “You’re joking, right? There’s no way that actually happened.” Quirky satire was the only way to go here, and I applaud everyone involved for taking that gamble.
19. Rounders
- Release date: September 11, 1998
- Budget: $12 million
- Box office: $22.9 million
- Letterboxd rating: 3.6 ★
- My Letterboxd rating: 4.0 ★
- Rotten Tomatoes: 64% (Fresh)
If you ever need someone to play an absolute prick who deserves everything coming to them, but somehow still kinda gets off easy, Edward Norton is your guy. If you enjoy any sort of gambling or casino-based movies, then this is for you. I immediately wanted to play poker after watching this movie, and this came out just a bit too early for the poker craze to catapult it’s box office performance. I’m still surprised every time I see the Rotten Tomatoes rating for this movie, I just don’t get it! The acting is really strong here from Norton and Damon, the plot is engaging and has high stakes (pun intended), and it has all aged really well. Sure, John Malkovich was really making a choice with his accent in this, but are we really going to get so caught up in it that we can’t see how great the rest of this movie is?
18. Gerry
- Release date: February 14, 2003
- Budget: $3.5 million
- Box office: $254,683
- Letterboxd rating: 3.4 ★
- My Letterboxd rating: 4.0 ★
- Rotten Tomatoes: 61% (Fresh)
“I hate you.” // “Not really though, right?” This is a polarizing film, to say the least. I think I loved it? It definitely tows the line of pretentious and provocative, but it was a bold choice that I think should be celebrated. This is not for the faint of heart though – not in a violent or gross way, but in a pacing and direction way. This movie consists solely of very long, no-dialogue takes where not a whole lot actually happens. This was right up my alley though, which is why it ranks so highly – because it was perfectly executed for what they wanted to accomplish.
17. The Bourne Supremacy
- Release date: July 23, 2004
- Budget: $75 million
- Box office: $290.6 million
- Letterboxd rating: 3.6 ★
- My Letterboxd rating: 4.0 ★
- Rotten Tomatoes: 82% (Certified Fresh ?)
The most underrated film in the franchise by far. The transition from Doug Liman to Paul Greengrass as director was the right call, but there wasn’t a massive tonal shift that made you feel like you were watching a totally different franchise. Plus, we love a good early-career Michelle Monaghan cameo. There isn’t a whole lot else to add here, because it is just another installment in the well-oiled machine that is the Bourne franchise. It delivers on everything you want out of it, and doesn’t run into any of the pitfalls that Jason Bourne did. A solid sequel in a world (and genre) where most sequels are pretty bad!
16. Air
- Release date: April 5, 2023
- Budget: $70-90 million
- Box office: $90.1 million
- Letterboxd rating: 3.6 ★
- My Letterboxd rating: 4.0 ★
- Rotten Tomatoes: 93% (Certified Fresh ?)
I already did an entire write-up of this movie, but here is a brief summary: I am so glad I finally got to watch this movie! I immediately felt sad that I hadn’t gotten to see it in theaters though – just something about it, made me wish I had a tub of popcorn in my lap and was staring up at a massive screen getting to watch this. Overall, it’s really not anything out of the ordinary – it’s a bunch of dudes sitting around talking about who they should try to sign to a shoe deal. That’s it. And we all know the outcome the whole time, too. And yet, I was engaged the whole time and couldn’t wait for the climax of the film, which was literally just a pitch meeting. But it was so good! Damon and Affleck’s chemistry obviously jumps off the screen which is great, while Viola Davis, Jason Bateman, Chris Messina and Chris Tucker round out an oddball, but lovable, cast. This was just fun to watch; I had a smile on my face for practically the entire film. I don’t really know or understand why they treated Michael Jordan’s character in the movie like Wilson from Home Improvement, but it was kinda distracting – definitely my biggest qualm with the film. It also felt a little in my face with all of the 80s music in the soundtrack, it was a little overkill. All in all, I really liked this movie. Definitely will be added to my “easily rewatchable” list when you just want a low-stakes, funny, feel-good movie to watch on a rainy day.
15. Contagion
- Release date: September 9, 2011
- Budget: $60 million
- Box office: $136.5 million
- Letterboxd rating: 3.4 ★
- My Letterboxd rating: 4.0 ★
- Rotten Tomatoes: 85% (Certified Fresh ?)
Boy I sure do hate how accurate this movie ended up being!
14. Ocean’s Thirteen
- Release date: June 8, 2007
- Budget: $85 million
- Box office: $311.7 million
- Letterboxd rating: 3.3 ★
- My Letterboxd rating: 4.0 ★
- Rotten Tomatoes: 70% (Fresh)
A perfect way to cap off a trifecta of really fun movies. They managed to up the stakes without feeling unrealistic (help out your friend who got screwed and nearly died because of it), while keeping the same charisma and cool factor of the first two installments, and not actually taking it that seriously. Everyone has their moment to shine, the music is killer like always, and the good guys win in the end. An incredibly rewatchable gem.
13. The Departed
- Release date: October 6, 2006
- Budget: $90 million
- Box office: $291.5 million
- Letterboxd rating: 4.3 ★
- My Letterboxd rating: 4.0 ★
- Rotten Tomatoes: 91% (Certified Fresh ?)
Imagine if this movie was made in 2024 and everyone was just aggressively pressing the screen of their iPhone instead of slamming their flip phones shut. Way less dramatic! Anyways, this movie is very good; however, I think it is also widely overrated. This is definitely the best Scorsese film I’ve seen, but it still falls into the usual traps that Scorsese struggles with – women are nothing but objects, the story is drawn out too long, and there are too many needle drops. That being said, I’m Shipping Up to Boston may be one of the greatest needle drops in cinematic history.
12. Ford v Ferrari
- Release date: November 15, 2019
- Budget: $97.6 million
- Box office: $225.5 million
- Letterboxd rating: 3.9 ★
- My Letterboxd rating: 4.0 ★
- Rotten Tomatoes: 92% (Certified Fresh ?)
After re-watching this, I am really glad that I was able to see this in the theaters when it came out. This is one of those films that was just made to be watched on the big screen, with the blaring surround sound of a theater vibrating your seat every time someone revved the engine of their car. Damon and Bale unsurprisingly nail their roles, with the cinematography taking a close second of my favorite things about this movie. My only real gripe was the use of VFX during some of the racing scenes. I think it would have been doable, and much more immersive, if they had used more practical effects instead of CGI. It just kinda takes you out of it a little bit. Overall, it’s a great movie and you certainly don’t need to know or care about cars or racing to enjoy it. Just a good ol’ high budget blockbuster with movie stars doing movie star things.
11. True Grit
- Release date: December 22, 2010
- Budget: $35-38 million
- Box office: $252.3 million
- Letterboxd rating: 3.8 ★
- My Letterboxd rating: 4.0 ★
- Rotten Tomatoes: 95% (Certified Fresh ?)
I have a lot of thoughts on this movie, but I’ll start with this: Westerns are not dead! $250+ million at the box office and ten Oscar nominations prove that if you know what you’re doing and put care and reverence into the story, people will not only turn up in droves, but will enjoy a good old-fashioned Western picture. Excellent performances from Damon and Bridges are almost completely forgotten about because of the outstanding debut of Hailee Steinfeld. The Coen brothers, along with Roger Deakins, continue blazing their path of banger after banger, and the “original” score accompanies their craft beautifully. If you’re not into Westerns (and their pacing) then this may not be the movie for you – but I suggest you give it a shot anyway.
I have to be honest with you – it was really, really hard leaving True Grit out of the top ten here. It’s objectively one of the ten best movies that Matt Damon has ever been in, and yet, it isn’t. That’s the thing – our guy Matt has just been in so many good movies, that you have ones like The Departed, True Grit, and Ford v Ferrari not appearing in the top ten! Obviously this is entirely subjective and your list may look entirely different, but you get the point. But that is also what makes film so amazing – we can all have differing opinions and rankings and tastes, and nobody is wrong for that! Get excited folks, next week we finally reveal my Top Ten Matt Damon movies of all time! Spoiler alert: it is just going to be full of me gushing over these movies and Matt Damon’s performance in all of them.
