Alan Rickman – Die Hard

One of the older actors in this gallery, the late Alan Rickman didn't make his film debut until the age of 42. Prior to that Rickman had mostly acted on stage, but in 1988 he announced himself to audiences as one of the most iconic action film villains in Die Hard's Hans Gruber. The role proved to be instrumental in bringing attention to the English actor, as he would go on to take on many memorable villainous roles over the course of his career—but it all started with his deliciously cool, calm, and calculative Gruber.