Xer Icon: John Cusack

Generation Xers don’t come any more iconic than John Cusack. For a quarter of a century, he has embodied, onscreen, a brand of philosophical outsiderness that typifies our generation in the best possible way: If anyone could be said to be sweetly cynical, it’d be Cusack’s characters. He has been the antithesis of the whiny, miserable slacker Xer critics deride us as. He’s the shining example we can point to and say, Look, we ain’t so bad.

In 1989, he was Lloyd Dobler in Say Anything..., who consciously opted out of the post-high-school corporate rat race. In 1997, he was Martin Blank in Grosse Pointe Blank (on which Cusack is also a credited screenwriter), self-employed hitman and high-school-reunion attendee who took advantage of that marker in time to reevaluate his life. And now, he’s Jake in Must Love Dogs: an artist and an entrepreneur suffering an early midlife crisis over both his work and his love life. For lots of people around Cusack’s age, his characters hit so close to home that it almost hurts.