Ben Affleck and Matt Damon

These two were friends even before high school, their parents introduced them at the ages of 8 and 10, and they’ve maintained their friendship for just over 40 years now. In the late 90s, they worked together to both write and star in Good Will Hunting, which netted them an Oscar.

This picture comes from the late 90s, from around the time Good Will Hunting was being filmed. I’m wondering if this was a candid or posed picture, seeing as Matt Damon is looking at the camera while Ben Affleck isn’t. Either way, they are rocking that sweet 90s fashion! I’d wear either of those shirts.