"I was a little taken aback." Then, when Kimmel asked about the possibility that both brothers would win Oscars, he got into the juicy stuff."This would be the very first time someone would win an Oscar who didn't brush his teeth from ages 10 to 14," he teased.
Keep reading to the five buzziest moments of the 45-minute conversation -- and watch the full video below.
On "Gigli" and the Bennifer phenomenon: "It could have been a bad movie no one cared about.
A month later, onlookers spotted the actor and the SNL producer acting flirty at The Heat premiere afterparty in New York City at the Stone Rose lounge, chatting and laughing at the bar. Would PEOPLE even be reporting this if she’d been given the heads up that Ben and Lindsay would be going public?
“He definitely looked interested in her,” a partygoer told PEOPLE at the time. Would PEOPLE be calling out Ben so openly as a philanderer if he had her blessing?
It's been two decades since Good Will Hunting earned Ben Affleck and Matt Damon an Academy Award for best original screenplay, and the longtime friends and collaborators celebrated the milestone when they hit the stage together at the Oscars on Sunday night.