Chevy Chase's 1976 departure from Saturday Night Live left a cast opening that Bill Murray was more than happy to fill. The Second City alum quickly made a name for himself on the sketch-comedy show with humor that alternated between the outlandish and the subdued. By 1979, Murray had cultivated a steady string of side projects and was filming movies like Meatballs and Where the Buffalo Roam whenever his SNL schedule allowed. He left the show in 1980, and thanks to Ghostbusters, by 1984 he was a bona-fide movie star.
Murray spent much of the 1990s bouncing between box-office flops and a series of bizarre cameos (Space Jam, anyone?). But in 1998, Wes Anderson's indie classic Rushmore revitalized his career. Anderson's emotionally-driven comedy allowed Murray to sidestep goofy roles for those better suited to his talents: the persona of a broken, socially-inept outsider who should probably go on antidepressants.