“The old Hillary was rigid and awkward; the new Hillary is loose and easy . . . going. . . . The old Hillary was driven by blind ambition and rage over her wasted potential, and her husband’s chronic skank-pronging. The new Hillary has shorter hair.”

If pressed to name when the Hillary Clinton sketch containing these lines aired on Saturday Night Live, many longtime viewers might need a minute. Through the years, Clinton has evolved as a public figure—and the narrative themes underpinning her story have transformed with her. Early on, Hillary’s portrayals on S.N.L. were less about her than they were about Bill Clinton, or the broader political landscape. Over time, as Hillary’s profile has risen in the real world, her S.N.L. story has become more her own. Still, some things never change: Clinton’s stiff image plagues her to this day, as pundits and comics alike continue to note her ambition and fervent, thinly veiled desire to be president. And through it all, S.N.L. has been watching—and holding up a mirror with countless timely parodies.

As the election draws near, Saturday Night Live fans will tune in to see how the show handles the insanity to come. They'll also witness the turning point of a legacy: it’s taken a total of nine actresses (cast members and guest stars alike) more than two decades to tell Clinton’s story so far. Now, America will finally see her campaign for the presidency through the final stretch. Vanity Fair spoke to both Ana Gasteyer and longtime Saturday Night Live writer Jim Downey about Clinton’s journey as one of Saturday Night Live’s most parodied public figures.

The “Long-Suffering First Lady” Era

Clinton’s S.N.L. legacy begins with Jan Hooks, who played her as a First Lady who viewed herself, above all, as a “co-president” to Bill Clinton. S.N.L.’s first sketch starring Hillary depicted a session on Nightline in which Bill Clinton (Phil Hartman) answered voters’ (silly) questions live as part of his campaign. Throughout the sketch, Hooks nods effusively, beaming at his every word. In the last couple of minutes, she becomes the focus when a voter asks for her cookie recipe. After Hillary rattles off the ingredients, the voter claims she didn’t adequately answer the question. Despite protestations, Bill chimes in, “Maybe it is Hillary’s fault . . . sometimes you can get so specific in giving the recipe that the overall vision of the cookie is lost.”

Even early on, it was the perfect symbol for what would turn out to be the long-running characterization of the Clintons: he’s the charismatic orator, and she’s the wonk.

Other notable sketches during Hooks’s tenure included a spoof of the Whitewater scandal and a cold open in which Hillary Clinton literally fights Bob Dole (Dan Aykroyd) over healthcare reform.