It’s no secret that Matt Damon is my favorite actor of all time. On April 12, 2023 I set out on the most ambitious movie-watching experience of my life1: to watch every single Matt Damon movie, in order of release, and rank them along the way. In total, I watched through 47 different movies that took just over eleven months and brought me to every streaming platform imaginable, and also relied heavily on the public library system for those movies not deemed worthy enough of being available online! I can admit here that calling this a career retrospective may be a bit misleading – I am no skilled writer, and I don’t have the eloquence or knowledge to write a legitimate career retrospective for one of the biggest actors of the 20th century. But what I can do is write about his career in my own way, and have some fun along the way.
Firstly, you may be asking yourself, “what qualifies as a Matt Damon movie?” That’s a great question, and I’m glad you asked. The answer is: whatever I decided. There wasn’t a hard and fast rule to what qualifies, but it went something like this: cameos don’t count, he doesn’t have to be the leading actor in it, and voice acting don’t count either. I am not taking anything away from animated movies, because voice acting is an entirely separate thing, which is exactly why I didn’t include them in this list. My aim when starting this was really just to go through and watch all of the Matt Damon movies I had never seen, but wanted to, since he is indeed my favorite actor. It’s only right that I call him that, if I’ve seen every single one of his movies.2 For that reason, movies like Field of Dreams, Mystic Pizza and Thor: Ragnarok did not make the cut.
Secondly: what did I base my rankings/ratings on for these movies? This was tough to decide when I was first starting this journey; do I rate the movies based on Damon’s performance alone, or on the quality of the entire movie? I decided on the latter, because a movie is always the sum of it’s parts, and not just the performance of one cast or crew member. There were several instances where Damon’s performance single-handedly carried the film, but that didn’t then bump the rating of the movie too much, as the overall viewing experience still remained fairly unenjoyable.
I figure what we’ll do is break this up into four parts, going through 11 or so movies in each part, and take a look at each film. I won’t go into nearly as much detail or analysis as I do with my other posts, because that would take way too long. But what I will do is give you the By The Numbers, along with a brief write-up of my thoughts on the movie. With that, I think it’s time to dive in. Godspeed to the both of us.
47. The Legend of Bagger Vance
- Release date: November 3, 2000
- Budget: $80 million
- Box office: $39.5 million
- Letterboxd rating: 3.0 ★
- My Letterboxd rating: 1.5 ★
- Rotten Tomatoes: 43% (Rotten)
This was a tough watch, but surprisingly, not the toughest on this list. This was one of Damon’s poorer performances, but I think a lot of that may be on the script, which didn’t do anyone any favors. There was a lot to not like about this movie, but the worst offender was the very controversial character of Bagger Vance, being a magical black man who helps a white man achieve his goals and inner meaning.
46. Hereafter
- Release date: October 22, 2010
- Budget: $50 million
- Box office: $107 million
- Letterboxd rating: 2.9 ★
- My Letterboxd rating: 2.0 ★
- Rotten Tomatoes: 47% (Rotten)
Ugh. This was the toughest watch on the list. This movie really soured me on Clint Eastwood as a director, and made me question why Damon would have signed on for such a weird movie. He does a good enough job with his performance in the movie, but it certainly doesn’t merit a viewing in my opinion. Best to skip this one altogether.
45. Elysium
- Release date: August 9, 2013
- Budget: $115 million
- Box office: $286.1 million
- Letterboxd rating: 2.9 ★
- My Letterboxd rating: 2.0 ★
- Rotten Tomatoes: 64% (Fresh)
I went into this thinking it would be pretty bad, but hoping I’d be proven wrong. The concept is there, which is why I hoped the execution would in some way follow suit, but it just disappoints on basically every level. The script was a hot mess and the characters had no depth or arc whatsoever. Jodie Foster’s accent was a choice and made her way less intimidating and believable. There was just so much about this that took me out of it anytime I felt myself getting slightly drawn in. The action sequences were clunky and the camera cuts every 1.43 seconds made it truly difficult to follow who was hitting who and what was actually happening3. Overall wouldn’t recommend watching this, which I hate to say. The pacing is pretty quick which makes it go by faster, so if you’re really wanting to watch it that will make it more palatable. I just don’t think it’s worth the time.
44. Downsizing
- Release date: December 22, 2017
- Budget: $68-76 million
- Box office: $55 million
- Letterboxd rating: 2.4 ★
- My Letterboxd rating: 2.5 ★
- Rotten Tomatoes: 47% (Rotten)
This movie either needed to be way more whacky a la Honey, I Shrunk the Kids, or way more serious a la…I don’t know, The Box? Either way, it just didn’t hit at all which is a shame, because it’s a very interesting concept. All I know for sure is that I need many, many more scenes in the future of Matt Damon tripping balls. That was a treat. Also, did the writers just forget after the first thirty minutes that they had hired Kristen Wiig? I was shocked we just never saw her again after the horrifying close up of her bald, one-eyebrowed head.
43. The Brothers Grimm
- Release date: August 26, 2005
- Budget: $80-88 million
- Box office: $105.3 million
- Letterboxd rating: 2.7 ★
- My Letterboxd rating: 2.5 ★
- Rotten Tomatoes: 38% (Rotten)
I noticed a disappointing trend with movies that Matt Damon is in that are overseen by the Weinstein brothers: the director and crew come in with one idea, the Weinstein’s combat with a different idea, and the viewers are left to pick up the pieces. It felt like the first third of the movie was what director Terry Gilliam was aiming for, but the rest of it felt like jumbled, over-serious Weinstein garbage. It’s a shame, because it’s another Damon performance that could have been really interesting, but ended up just being disappointing and boring.
42. All the Pretty Horses
- Release date: December 25, 2000
- Budget: $57 million
- Box office: $18.1 million
- Letterboxd rating: 2.8 ★
- My Letterboxd rating: 2.5 ★
- Rotten Tomatoes: 32% (Rotten)
This movie was plagued, like everything else he touches, by Harvey Weinstein. I would really be interested to see the Billy Bob Thornton director’s cut, because I think it would be a film I’d actually be interested in.4
41. School Ties
- Release date: September 18, 1992
- Budget: $18 million
- Box office: $14.7 million
- Letterboxd rating: 3.3 ★
- My Letterboxd rating: 2.5 ★
- Rotten Tomatoes: 60% (Fresh)
The acting in this is fine at best, but my god was the writing so heavy-handed that I knew what was coming around every corner so easily that it made the viewing experience fairly boring. Željko Ivanek once again nails the role of a sniveling POS, but then his character just…disappears for the second half of the movie? It felt like they were trying to have us leaving this movie with a feel-good spirit because Van Kelt turned his roommate in, but I was still just left hating almost every character except for David and Reese. At the end of the day, you’d be better off just watching Dead Poet’s Society instead, but it did leave us with this absolute chef’s kiss of a mic drop from Fraser: “No sir, you’re never going to forget it. Because I’m going stay here and every day you see me, you’ll remember that it happened. You used me for football. I’ll use you to get into Harvard.”
40. Stuck on You
- Release date: December 12, 2003
- Budget: $55 million
- Box office: $65.8 million
- Letterboxd rating: 2.6 ★
- My Letterboxd rating: 2.5 ★
- Rotten Tomatoes: 61% (Fresh)
For me personally, I needed this movie to either go all in with the schtick/comedy (i.e. Dumb and Dumber) or go all in with the feel good/dramatic sense with a little comedy on the side. Either way, a light-hearted movie that is an easy and relatively fun watch that proves Donald Trump was only the second best 2016 presidential nominee to appear in a movie5.
39. Margaret
- Release date: September 30, 2011
- Budget: $14 million
- Box office: $623,292
- Letterboxd rating: 3.9 ★
- My Letterboxd rating: 2.5 ★
- Rotten Tomatoes: 75% (Certified Fresh ?)
I gotta be honest, this just didn’t do it for me – and I’m well aware that I’m in the minority. It’s a classic tale of the studio and director not seeing eye to eye, and the movie ultimately being the one that suffers. Director Kenneth Lonergan wanted a 3+ hour cut, but the studio wouldn’t take anything over 2.5 hours. Also don’t let the 2011 release date fool you, the movie was filmed in 2005 (which is why everyone looks so young in it). Even with all that in mind, I still don’t think this would have been for me. Anna Paquin absolutely nailed her role, but I think that’s almost why I didn’t like this – it focuses so much on teen angst and melodrama and main character syndrome that it took away from the viewing experience for me; it just came off as grating. This movie also kinda falls in the “crying hard and yelling ≠ good acting” category. Jean Reno, Kieran Culkin and John Gallagher, Jr. are a delight, as they always are.
38. Dogma
- Release date: November 12, 1999
- Budget: $10 million
- Box office: $44 million
- Letterboxd rating: 3.5 ★
- My Letterboxd rating: 3.0 ★
- Rotten Tomatoes: 68% (Fresh)
To slightly change up a great quote from Jake Peralta in Brooklyn Nine-Nine: “Classic film, one of my childhood favorites. And it only gets overtly homophobic throughout the entire thing, so a win.”6
37. Geronimo: An American Legend
- Release date: December 10, 1993
- Budget: $35 million
- Box office: $18.6 million
- Letterboxd rating: 3.2 ★
- My Letterboxd rating: 3.0 ★
- Rotten Tomatoes: 50% (Rotten)
A well-intentioned film that overall misses its mark. There are some beautiful shots throughout of the southwest mixed with great cinematography and acting from Wes Studi that help carry you through the otherwise boring, and rather slow, pace of this film. It just felt at times as though I was watching a four-hour History Channel documentary, rather than a Hollywood movie production.
36. The Adjustment Bureau
- Release date: March 4, 2011
- Budget: $62 million
- Box office: $127.8 million
- Letterboxd rating: 3.1 ★
- My Letterboxd rating: 3.0 ★
- Rotten Tomatoes: 72% (Fresh)
This movie was good but had the chance to be great. The plot in principal is interesting, but I just don’t like what felt like the “safe” bet of it being heavy Christian undertones, with the chairman being God and the case officers being angels. Damon and Blunt have electric chemistry which bumped my rating up basically a full star. I’m surprised it took this long into Damon’s career for him to play the all-American politician that mostly relies on his charm alone to get elected. All in all it’s a pretty average movie that succeeds as much as it does due to the great casting and potential of the screenplay.
35. Invictus
- Release date: December 11, 2009
- Budget: $50-60 million
- Box office: $122.2 million
- Letterboxd rating: 3.3 ★
- My Letterboxd rating: 3.0 ★
- Rotten Tomatoes: 76% (Certified Fresh ?)
I feel like this movie really suffered from Clint Eastwood directing it. I have nothing against the guy but he made some really weird choices, like making the last TEN minutes of the game be in slow motion?? I thought the DVD I was watching was broken, but no: there is legitimately ten straight minutes of slow motion at the climax of this film. Imagine watching The Matrix, but the entire fight scene between Neo and Smith in the train station is in bullet time. Just a brutal decision to make.
Listen, even the greats have some duds. While I still believe that most of the issues with the above movies were not Matt Damon’s fault, there is no two ways around the fact that a lot of them were not the most enjoyable viewings. I was glad to say that I watched them, and can have a better perspective on the entirety of Matt Damon’s acting career, but I am also glad to know that there are a lot more films he’s been a part of, that really set the tone for why he is hailed as one of the best. Stay tuned for Part Two, where we will cover numbers 34 – 23 on my rankings list!
- Before this, my most ambitious movie-watching experience occurred in 2020 when I went through and watched every single Marvel movie (in the MCU canon) in chronological order. At the time, that consisted of 22 movies. ↩︎
- This is just a qualifier for me, and a ridiculous one at that. Don’t feel like you need to hold yourself to this kind of standard in order to call yourself a “fan” of someone or something. ↩︎
- If you’re a fan of the WWE, this may remind you of the complaints that viewers often had during the tenure of longtime Executive Producer Kevin Dunn, who also had a tendency to jam as many camera cuts in to the most pivotal moments of a match. Here’s an example. ↩︎
- Please do yourself a favor a take two minutes to read the Production section of the Wikipedia article for this movie. It says everything you need to know about why this movie didn’t work. ↩︎
- Ben Carson makes an appearance as a surgeon (which he was in real life) in this movie. ↩︎
- The original quote, which is referencing Ace Ventura: Pet Detective: “Classic film, one of my childhood favorites. And it only gets overtly transphobic at the very end, so a win.” ↩︎
