Jason Schwartzman – Rushmore

Compared to other actors in this gallery, Jason Schwartzman likely had the easiest path to landing a film role, being part of the vaunted Coppola family. Because of that upbringing Schwartzman grew up around those in Hollywood, but that isn't to say that the actor wasn't deserving of his casting in Wes Anderson's Rushmore. As Max Fischer, Schwartzman would display the kind of quirky performance that would make him a staple in future Anderson collaborations and endear him to fans over the next few decades. With no acting experience to his name at that point, Schwartzman was praised for fully embodying his character.