The Outsiders is one of our ultimate ’80s flicks, mainly because it featured a particularly hot gang of greasers that included a young Tom Cruise and Rob Lowe. The babe that really stole our hearts, though, was Matt Dillon. The movie launched his career and we’ve been swooning over him (and those eyebrows!) ever since. Whether he’s shirtless, leather-clad or…um…shirtless, he’ll always be one of our favorite bad boys.