Matt Damon and Ben Affleck, (pictured at the One X One in Toronto on Sept. 9, 2007) started their bromance as street-wise 8-year-olds in Boston and have been tight ever since. They hit it big with their Oscar-winning smash Good Will Hunting, which they wrote and costarred in, and they remained close as they secured their A-list status. "We went on vacation last summer," Affleck told People.com in 2009. "It’s nice. It always has been."