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How Cher Horowitz Became Gen Y's BFF

The ultimate girl crush.

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1997 was a big year for me: I learned leg hair was a scourge to be eradicated at all costs, Jockey training bras were the bomb, and Clueless was the greatest movie ever.

I was twelve, suddenly surrounded in a girl's world of my own creation with a fourteen-piece Lip Smackers collection, a stack of Hello Kitty notebooks, and a Leo DiCaprio closet collage/shrine. It was a stark contrast to whoever I'd been before, and the night someone popped Clueless into the VHS at a slumber party, Cher Horowitz managed to validate my entire existence. Clueless became my baseline barometer for cool and my guide to aspirational living — and, I'm not ashamed to admit, has remained deeply central to my life ever since.

Back then, I missed the note of satire; all I knew was Cher had a cell phone and a whole computer-controlled room for a closet. (A whole room, people.) And that was enough. Cropped sweaters and knee socks colonized our wardrobes. My friends and I learned to walk and talk like Cher, putting our thumbs together in W signs to our parents' faces. Surfin' the crimson wave! Full-on Monet! Where's my white collarless shirt from Fred Segal? Did we have any idea what any of this meant? As if.

It pains me to acknowledge an uncomfortable fact about my early relationship with Clueless, which is that I occasionally watched Clueless...the TV show, which was on the air between 1996 and 1999. It may be the worst show of all time. If you want to torture someone, lock them in a room with this cheesy sitcom where the characters are seemingly doing whip-its and shopping at Fashion Bug; they will lose it.

The unsettling truth about Clueless the TV version is that it was dumbed down for people like me — young teenagers of the late nineties — who were too dumb/not worthy of relishing movie-Clueless's poetic gems.

I like to think that, in my semiserious quest in becoming a full-time Cluelessologist, the TV version left me unscathed. Because as I got older, the original Clueless continued to yield rewards. Like a Bloomin' Onion, it revealed deeper layers of comedy, commentary, and complexity with each viewing. This movie would tell me that Billie Holiday was not a man; that famous quotes came from Shakespeare, not CliffsNotes; and that "jeepin'" was not, strictly speaking, an extreme back-roading sport.

I won't tell you how many times I've seen Clueless, but I will tell you it's enough that I can pretty much recite the entire thing from memory. Sometimes when I can't sleep, I play the movie in my head, fast-forwarding through the scenes, testing my knowledge of the film's sequence.

The gift of Clueless kept on giving all through college, where I devoted term papers and impassioned speeches to the defense and dissection of Clueless as a seminal cultural document. You might even credit Cher and Co. with my choice to major in American Studies — home to film-school rejects and vinyl-clutching radio station denizens — where I acquired such real-world skills as waxing semiotic on the significance of Chuck Taylors and reality TV. And like Cher and her prototype Emma before her, I eventually learned that the joke was on me when I tried to find gainful employment armed with this dubious skill set.

What makes director Amy Heckerling's masterpiece so remarkable is that it grew up with me and never lost relevance. There aren't many things you embrace at age twelve that will continue to entertain and enchant for all sorts of equally valid, totally new reasons at sixteen, and twenty-one, and twenty-six. And while I did, at some point, have to come to terms with the fact that plaid schoolgirl suits never were and will probably never be an acceptable form of dress, I never lost my affection for Cher's sartorial bravado. And in all other areas, she remained untouchable as an icon of cool. Because while my appreciation for the movie deepened over time to include a smug grasp of the pop-cultural pastiche and postmodern shtick of it all, I never lost my original pleasure in the simple story of a girl who thinks she can control everything and learns that the world is full of surprises.