At a screening of "AIR" in March 2023, Matt Damon shared that Ben Affleck gave him some direction when they were only kids. The "Martian" star told Indiewire, "Well, it might seem like the first time he's directed me. I mean, we did high school plays where he was like, 'Dude, I think you should do it like this.' He's been directing me for like forty-something years." Affleck also quipped, "It's not the first time I've carried him!"

While the actors started their careers at young ages, their first shared movie appearance wasn't until 1989 as extras in "Field of Dreams." However, achieving stardom in Hollywood is no easy feat. It took Affleck and Damon eight more years and two more movies together before they won their first Oscars. The friends shared that special moment on stage, standing side by side, as they received their Academy Awards for Best Original Screenplay for writing credits on 1997's "Good Will Hunting." The special guests Matt Damon and Ben Affleck brought to their first Oscars also created an online buzz as they mirrored each other.

In an interview on The Tonight Show in 2021, Affleck revealed to Jimmy Fallon that they never thought the movie would get released. The two agreed that "Good Will Hunting" was made to be an acting reel. No one was hiring them then, so they decided to believe in one another and write a movie themselves. It speaks to an amazing and supportive friendship between the two stars.