Ben Affleck has directed five feature-length films so far. I ranked them all here. If he directs more, I’ll add them. He has had an interesting (if very inconsistent) career behind the camera so far.
5. Argo 
Ben Affleck used his skills that he fine-tuned on fun Dennis Lehane thrillers only to sell out to make a slick piece of CIA and Hollywood propaganda. The way he paid for it though karmically in a “chickens come home to roost” sort of way professionally and personally in yet another fall from grace was fitting though! This film spawned his second downfall which then of course led to his third rise. The man is a beast.
4. Live by Night 
Ben Affleck just flew too close to the sun here, and that is something perfectly in line with the Ben Affleck persona. Yes, this film may be a hilarious embarrassment in every way, shape, and form, but it’s dumb in a very particular way that makes it endearing. The fact that Ben Affleck has glaring strengths and weaknesses but is not aware of which is which yet is a key part of who he is and allows his strengths to be so lovable. We as a society love to forgive Ben Affleck for his foibles but without foibles we would have nothing to forgive him for and thus he would be nothing. Also, it’s not CIA propaganda so.
3. Air 
Air became an almost instant artifact of its time. Whether the film is remembered fondly or negatively, the film should be considered relevant to capturing something about this country.
On the surface, this movie is structured and tonally feels like a feel-good story. The story of the origins of the Air Jordans is told from the perspective of the Nike employee who pushed the hardest to sign Jordan and then ends on a note framed as a victory for workers everywhere.
In the United States though, that story is not necessarily feel-good. You have to accept the premise of the country’s basic setup to see this movie as feel-good rather than somber. Two scenes from the movie really stand out when you think about what the movie is putting out there.
Marlon Wayans has a small but significant scene where he provides some context for Matt Damon so that he can figure out how to approach Michael Jordan’s family. He is a former Olympic assistant coach who once accidentally worked security for the infamous “I Have a Dream” speech, and MLK apparently gave him the paper of the speech as he walked off the stage. Wayans then discovered that the “I have a dream” part of the speech was ad-libbed. And Wayans’ character uses this anecdote about Martin Luther King to inspire Matt Damon to go with your gut which in turn gives Damon the inspiration he needs to……close a Nike sneaker deal with Michael Jordan.
The other key scene what I am calling the “Born in the USA” scene. Jason Batemen decides to remind Matt Damon of the human costs of this situation and ham-fists in an anecdote about his realization one day that “Born in the USA” is not a patriotic song and basically about how fucked up the United States is only no one seems to know that. Bateman then makes a labored connected to that anecdote and the fact that Nike does not make their shoes in an ethical manner.
The question then becomes, does Air know that the Michael Jordan and Nike making billions of dollars off of selling shoes for the last forty years is not really like some feel-good story? Michael Jordan and Nike is significant for understanding post 60s America though.
At some point, it stopped seeming like things could get better for us as a whole. And all that was left was for the clock to run out and for those who could to get what they can while they still could. That is probably the key to this movie’s hugely positive response. It is a nostalgia picture. Not for when things were better. But for when we did not know how much worse it was going to get.
2. Gone Baby Gone 
From the beginning, Ben Affleck has displayed a knack for directing dumb Boston crime movies. It truly is his wheelhouse! Is it a limited wheelhouse?? absolutely but who cares. He directs them with love and care and makes them slick and well-paced enough with overly strong casts to be quite pleasant to watch. He also has a knack for managing to get 1-2 standout performances from his cast in his dumb Boston crime movies, with Amy Ryan and Ed Harris doing the honors here. A very fine debut feature.
1. The Town 
Affleck’s masterpiece and likely something he will never top. Affleck has a talent for playing dumb people and making dumb Boston crime movies, and this movie combines both into the ultimate Affleck experience. Even besides all of that stuff though, The Town is simply just a slick crime thriller with a fantastic cast and manages to excel at the majority of the things it is trying to do. It is a great lane for Affleck to pursue as a filmmaker, and the further he strays from it the more likely the quality of his work will wane. This film is also noteworthy for being a worthy inclusion to the Jon Hamm Himbo Canon. His character here is just stunningly dumb in ways that call to mind his role on 30 Rock. Kudos to all involved for pulling that off.