6. Jersey Girl (2004)
Affleck’s career was in big trouble when this movie came out. He had starred in major box office bombs back-to-back and one of them “Gigli” starred his partner Jennifer Lopez. “Bennifer” was all over the tabloids which hurt his image as a “serious actor” and some people were already exhausted from seeing them or hearing about them. Affleck kept pushing Kevin Smith to write this one and Kevin once jokingly responded “one of us won an Oscar for writing and that’s not me”. The film had co-starred Jennifer Lopez but the studio has played down her role to not make the audience feel that they’re going to watch “Gigli 2”. Some of her scenes were also cut after their real-life split.
Still, “Jersey Girl” is still a charming, lovely movie. It’s incredibly conventional, and somewhat sentimental but it doesn’t feel phony. Affleck, who once talked about how much he’s proud of making “Bounce” (2000) probably has a fondness for such material. It feels like a heartfelt tribute to fatherhood, Affleck is good in in it and George Carlin’s last scene is wonderful. It alienated some of Smith’s fans and flopped at the box office but it’s better than its reputation suggests. Oh and of course, Damon cameo is always a nice surprise.
5. Chasing Amy (1997)
After a while, it feels like it’s rather ranking of Kevin Smith movies than the films of Affleck/Damon duo. Especially because Affleck had bigger role in those compared to Matt but then again, Damon is the master of cameos, so it doesn’t matter. Damon is once again cameo and it’s always nice when he pops up but the lead star is Ben Affleck, giving one of his finest performances as Holden McNeil. He falls in love with a fellow comic artist, Alyssa Jones who identifies as a lesbian. “Chasing Amy” had some mixed reception even back in then but it was still considered to be Smith’s most mature and affecting work at that time.
The screenplay and the performances were particularly praised and is probably the only time where Smith came close to an Academy Award nomination for screenplay. As for its sexual politics, it’s up to you to watch and decide if it has aged well or not. Some of it probably have aged well, and some other stuff have not. Even Smith is not sure if it has aged well, however, he mentioned in a tweet that it was written by “a 26 year old Jersey boy in 1996 who was desperately trying to think outside of his hetero box. He’s not woke, he’s waking up”. Certainly, it’s an unusual film for its time and features some of Smith’s best writing with honesty and sensitivity. The performances are universally strong.
4. Dogma (1999)
Now is it really better than “Chasing Amy”? That’s up to debate. You can even discuss if it’s funnier or better than “Jay and Silent Bob Strike Back” or not but it deserved a ranking this high because finally, our boys gets more time to spend together. The story revolves around two fallen angels – Bartleby (Ben Affleck) and Loki (Matt Damon) – who plan to employ an alleged loophole in Catholic dogma to return to Heaven after being cast out by God.
It’s hard to say if “Dogma” is entirely successful at its satire or is it even much thought-provoking but it was a rare type of studio picture regarding its tone and subject matter. That alone makes it a unique film. Sure, if you don’t like Smith’s juvenile humor, it can be off-putting but still, it’s clever enough to make it a worth-watch even for his haters. Even if you won’t end up liking the film, one has to admit it’s a “noble failure”. Alanis Morissette cameo as God is still brilliant but it’s fair to say Affleck/Damon duo steals the movie, with Affleck even being somewhat scary at some point. It’s strange that despite people often associating them together and them also having great on-screen chemistry, they didn’t end up as co-leads in a movie for years to come.
3. Air (2023)
Ben Affleck reinvented himself as a serious actor with his role in “Hollywoodland” and then started to earn further acclaim with his directorial efforts, “Gone Baby Gone”, “The Town” and “Argo” which brought him his second Oscar win. His next effort “Live by Night” failed and that’s why he had to be careful for his next project to not turn into George Clooney who also had directed fine films early on but then kept making turkey after turkey afterwards.
This is more comic in tone than his previous efforts and the second period piece thriller and it works well. The script is praised for being sharply written, some critics even went as far as to compare it to “Jerry Maguire”. Another reason why they made comparision is because the business side of sports world can be boring to many but Affleck, just like Crowe before him, found a way to narrate the story in a fun, dynamic way for the audiences.
Everybody shines but Damon is a rock-solid lead. You can easily see why this guy had been one of the biggest movie stars in the world for decades now. Affleck’s own performance feels like a comedy relief for the movie, he doesn’t necessarily do transformation but he’s fine in the role. It’s absolute pleasure to watch Affleck and Damon go at each other on screen. It’s also the first Affleck directs Damon in a movie and hopefully, not the last.
2. The Last Duel (2021)
Affleck and Damon didn’t write anything together since their Oscar-winning screenplay for “Good Will Hunting” up until “The Last Duel”, one of the most underrated films of 2021 whom we hope will have more fans in years to come. They collaborated with always great Nicole Holofcener on the script and let Ridley Scott direct the material. They all did a great job. It’s an astonishingly well-made historical drama that has a lot to say, not just about the history but also about many modern day issues.
Presenting the film in three different narratives is a great idea and it works particularly well for to deliver its message. The final last duel scene is indeed brilliant. Affleck’s performance is a show-stealing one, he takes on a character that he never did before. He’s seemingly having lots of fun with the performance but he doesn’t turn it into something comical. It’s fitting the film’s tone very well and Damon is also brilliant in the leading role, also playing a character that he rarely did in his career. It was a great year for him in general, with this one, “No Sudden Move” and “Stillwater”, all three are among his best performances but the movie industry was still recovering from COVID-related problems and almost all of them were overlooked. Still, it’s a movie that they both can be proud.
1. Good Will Hunting (1997)
Finally, the number one is not all unexpected. An orphan who is exceptionally talented in mathematics but who has troubled relationships at the same time is sentenced to therapy with a psychologist who, after the loss of his wife, has disconnected from life just like his young patient. Is the movie really that much of an original? Probably not but it works amazingly well for so many reasons. The dialogues are so well-written, the acting performances (Damon and Affleck included) are powerful and Gus Van Sant’s direction is very sensitive.
For a studio drama, it feels very honest and refreshing. It should be studied by some that how enough of quirks, the original lead character and emotionally rich material can make you easily forget that you’re watching a film with a predictable arc. It is considered to be one of Robin Williams’ most applauded performances for a reason. His conversation with Damon on Boston Public Garden is one of the most iconic scenes of its time.
Damon got an Oscar nomination for his performance and they both won Oscar for writing, and that was the beginning of their stardom. Since then they kept working, sometimes together and made lots of great stuff. This is a warm and tender story, one of the best films they’ve created, and also a success story in a way how they’ve tried so hard to make this project finally happen. This one and “The Last Duel” are probably the best films they’ve co-starred and here’s hoping they’ll keep on writing more things together in the future.