In the late 1990s, there was a short-lived TV show about the movie industry titled “Action” starring Jay Mohr, who ironically stars in the latest Damon/Affleck feature “Air”. The show was great enough with some sharp writing but it didn’t last long. In one episode, a character complains about how it’s hard to write a screenplay and Jay Mohr character responds “Ben Affleck and Matt Damon have won an Oscar for writing. How hard can it be?”. The line is certainly funny or maybe was funny because it shows how people were still not taking them seriously enough.
Damon and Affleck are the definition of “friendship goals” who worked together in many films, produced things together, supported each other, and became major movie stars in their own way. Damon had easier scoring strong films back to back. For Affleck, it was fashionable to hate him in the early 2000s when his films like “Pearl Harbor”, “Daredevil” and “Gigli” were flopping back to back. He turned the tides by starting to direct his own movies and then getting better parts more frequently.
Recently, he and Matt started to write screenplays again after a long break and starred in films together in major roles. Their last film “Air” marks a new era of creative collaboration for the duo, who recently teamed up to create Artists Equity, a production company that where Affleck is the chief executive, while Damon is the head of content. That’s why it feels like a good time to look at their previous collaborations.
12. Field of Dreams (1988)
Have to admit, went back and forth with this one. It comes up in the last place not because it’s a bad movie but because it’s hard to classify it as “Ben Affleck/Matt Damon movie”. So, hopefully you’ll read this before thinking “whoa, Glory Daze is better than Field of Dreams?”. No, it’s not, but that one and others are more fitting with “Affleck/Damon movie” phrase. Yet, couldn’t skip this one. it has to be here because they’re both in it even though it’s hard to distinguish them on screen.
“Field of Dreams” is a classic baseball drama and its sentimentality warmed lots of hearts in the late 80s, even if its critics reception was more mixed. It was another big hit for Kevin Costner and also helped the late, great Ray Liotta to gain more prominence. It’s also worth noting because they both made their big-screen debut as uncredited extras here. Damon stated the main reason why they were in the film was that the call for extras was at the Red Sox’s baseball arena, Fenway Park.
The movie made a huge impact on them, overall it was their first experience on a major Hollywood film set and Costner was someone who was generous with his time and hung out with extras. Our duo was bit starstruck and how Kevin would know that they’re gonna be big stars as much as him someday. Even though it’s near-impossible to catch them on screen. It’s never bad to have a classic film like this one on your IMDb resume.
11. Glory Daze (1995)
Ben Affleck’s first lead role, or “sort of lead role” with his own words. He’s good but he’d benefit a lot If the writing was much better. The 90s had lots of Gen Angst movies but the problem is “Glory Daze” was unsure of what kind of movie it actually wants to be.
It feels like a mix of “Reality Bites” and “Dazed and Confused” or as one critic described it, Baumbach’s “Kicking and Screaming” only with macho bro types. There are some fine jokes early in the movie but as the film progress, it gets kind of dull. There’s not much of a plot to speak of but the events don’t feel like a glimpse of real life also. As for Matt Damon, he has a non-speaking small role as former El Rancho housemate Edgar Pudwhacker.
The film has other notable cameos including from Brendan Fraser and Matthew McConaughey, Damon’s future “Interstellar” co-star and honestly, if you just watch Matt Damon’s McConaughey impression on Letterman, it’d be more entertaining than watching this entire film. Still, it probably has its moments and it’s interesting to watch Affleck in his first leading role.
10. The Third Wheel (2002)
One of their lesser-known efforts, “The Third Wheel” is one of those Miramax titles that they’ve kept for years and then suddenly decided to dump it. For most of the world, the movie went straight-to-video despite featuring some big names in the cast.
Shot in 1999, the movie stars Luke Wilson who was in so many of such films back then and Denise Richards, who was having a streak with back-to-back roles in “Starship Troopers”, “Wild Things” and “The World is Not Enough”. She’s particularly charming in this one. Weinstein-led Miramax had a weird tendency by either totally ignoring their movies or campaigning non-stop for them to an exhausting level. It little had to do with the quality.
“The Third Wheel” is a unremarkable but fine rom-com, something you’d appreciate more if you have a soft spot for 90s studio romantic comedies. Affleck has a bigger role , playing sort of a goofball while Damon is only a cameo but his cameo is one of the film’s highlights. Not only he shows up unexpected but the scene is funny enough. Strange enough, it’s probably one of Affleck’s finest roles in that era because unlike some of the leading roles he got at that time, he’s hardly boring here. Then there’s a silly musical number at the end which is worth to see.
9. Jay and Silent Bob Reboot (2019)
Kevin Smith was huge in the 90s. He had an incredible following, so many fans and his films probably spoke to a generation. The critics enjoyed many of his stuff as well, even though they found his humor immature at times. He was this comic book fan who also seemed intelligent which helped him to gain even bigger audience. Ben Affleck and Matt Damon were his frequent collaborators and close friends. Affleck and Smith met during the audition process for Mallrats in 1994, and at the time, Affleck credited Smith’s directorial debut, Clerks, for inspiring him to co-write his own screenplay that he’d just sold. They haven’t collaborated in years till Kevin Smith called him and Matt once again for brief cameos – in roles that their fans will easily recognize for this movie.
“Jay and Silent Bob Reboot” is hardly a good film. It doesn’t have anything original going on and almost zero memorable sequences, however, as it’s been mentioned, these movies meant a lot to a generation. So if you were raised with Kevin Smith movies, this is a fun nostalgia trip. Not bad at all, especially compared to Smith’s next (awful) nostalgia attempt in “Clerks 3”. If you don’t like Smith, his humor or these characters, it’s better to skip it. It’s not even one of Damon’s best cameos but he always adds something to his brief appearances.
8. School Ties (1992)
Brendan Fraser have earned some acclaim for his performance in the leading role in “School Ties” but after the way his career took off, no one expected him to become an Oscar winner someday. He’s decent enough in the leading role as a Jewish high school student who is awarded an athletic scholarship to an elite preparatory school in his senior year.
The film is based on co-writer Dick Wolf’s own experiences and it has some powerful moments but still, the movie has such a non-complex leading character and the message is so loud and clear that it feels like an Afterschool Special after a certain time. It’s well-directed and the acting is fine enough, especially by Matt Damon who steals the show from Fraser but the writing is just not there. It’s very predictable which is okay but when you make a predictable movie like this, then the clichés must at least be handled in a way that would feel fresh. The film doesn’t earn that and for a movie setting in 50s, it doesn’t feel like it.
Still it showed a lot of promise for Damon, whereas Affleck had a brief appearance. Damon, disagrees by the way on the complexity of the subject. “The part was interesting because of the complexity of the role,” mentioned Damon. “Until the conclusion of the film, you really can’t figure out if he’s good or bad.” It’s obviously a serious subject matter but deserved a better movie.
7. Jay and Silent Bob Strike Back (2002)
Probably the end of Kevin Smith’s streak of successful comedies. Again, as it’s been said on the other Jay and Silent Bob film on the list, it’s another movie that depends on how much you liked Kevin Smith’s signature humor style but if you do like him, then it’s one of his bests for certainly. It’s more outrageous and has more crude humor than “Mallrats” and that’s what makes it fun. Obviously, Smith’s target audience was teenagers but it worked out well for them.
The movie wasn’t a smash hit but it was a commercial success for what it is. However, given all the stars involved, the lead actor Jason Mewes wondered why it didn’t turn out to be a bigger hit. Indeed, this was also the time when Affleck and Damon were already big stars, so Smith used their appearances in a meta way. It’s fun to watch, especially if you’re fan of the two.
Affleck, in particular, plays himself, his characters from “Chasing Amy” and “Good Will Hunting” (as does Matt Damon), and is also the voice of Guard Over Radio. If you loved this as a teenager and is scared to go back, it’s understandable. Some of it is definitely not aged well and even might be considered as offensive, but some of it holds up well. Or maybe it’s just the nostalgia.