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Amy Heckerling’s Clueless turned twenty this year, and to celebrate, pop culture writer + critic Jen Chaney decided to make a book about it. Not just any book, either; As If! takes the oral history route via interviews with the iconic film’s cast and crew, resulting in a fantastic compilation that belongs in the library of any true Clueless fan. Since Jen will be speaking about the book this Wednesday in DC (at Kramerbooks & Afterwords, 6:30pm), I recently caught up with her over the phone to talk about the massive (but fun) undertaking, and (of course) what it was like to interview Paul Rudd. (Insert HUBBA HUBBA here.) Read up on all of that (and more) below, and then continue your literary adventures by grabbing a copy of As If! and catching Jen live and in-person this Wednesday. HERE WE GO:


So first of all, congratulations on the book release! I mean, did you ever think you would be writing a book about Clueless? Was there even an inkling of the amount of impact the film would have the first time you saw it?

I saw it towards the end of 1995, which was after it’d become a hit, but I think in the case of any movie, to really understand the amount of lasting cultural impact it’s going to have you need a little bit of time to pass. So even though I really liked the movie the first time I saw it, I would not have necessarily thought, “Gosh, I’ll probably write a book about this someday!” [Laughs] Because at that point, I was in my early twenties, and I couldn’t grasp the idea of myself writing a book about ANYTHING, but also, I think the cultural impact that it’s had is something that I don’t think most people (including the ones who worked on the movie) truly appreciated until some time had passed. So no, the first time I saw the movie I couldn’t have envisioned all of this happening.

And I’m assuming you’ve had to watch it at least a few more times in the last twenty years; how many times would you say you watched it in order to write this book?

I wish I’d done a better job of keeping track of how many times I watched it, but I think the best estimate I’ve come up with is fifteen to twenty times from front to back (maybe more), and then probably fifty times for certain scenes. And it’s weird, because you’d think I’d be sick of it, but I’m not! In fact, I was doing a TV interview and they were showing clips on the monitor before the interview started, and I was like, “Why don’t we just pause and watch this for a little while?” [Laughs] I think there’s something so engaging about it that you can watch it over and over again and it’s like an old friend; you don’t get tired of it.

So what was your overall writing timeline like from start to finish, then?

It was a pretty compressed timeline, because the proposal was circulated, and I pitched the idea with my agent and sort of got the sign-off at the beginning of last summer. We knew we wanted to time the release around the twentieth anniversary, because that just seemed to make the most sense, and because we knew we were pretty tied to a publication date around July of this year, that meant that I had to get the initial manuscript written in about six months. Then there were two or three months where I was still going through with my editor and I was able to get a few last interviews that I hadn’t been able to get before that point and weave them into the text, but the bulk of the manuscript was written in about six months. And with something like this, where it was so interview-intensive, it was pretty fast.

Right, right. And when it came to finding a publisher, were you like Heckerling and having to kind of shop it around a little bit, or was there enough buzz around the anniversary that you had the opposite experience?

My agent sent out the proposal to a bunch of different places, and there were several publishing houses that were interested. And then I came up to New York and we went and had meetings, and all of them wanted to publish it. So there was actually kind of a bidding war, and I was like, “Really? Wow, okay!” [Laughs] But Touchstone were one of my top choices, because when we had all of these different meetings, I felt really good about that one in particular. And purely by coincidence, my editor went to the same high school as I did (not at the same time, I didn’t know her at all but had just realized we went to the same high school) and it just felt like it made sense for my editor and I to have gone to the same high school in writing this book about one of the best high school movies ever made. So it worked out, but yeah, there were multiple publishers that were interested, and I think a lot of that had to do with the fact that a lot of the people I encountered at these publishing houses were women in their early thirties who loved Clueless; you didn’t even have to try to convince some of them that this would be worthy of a book, because they were already on board with it from minute one.

Well, that’s obviously the ideal scenario! I mean, clearly that nostalgia factor is of critical importance in all of this; it does feel like it has a very specific time period attached to it, but it simultaneously feels incredibly timeless. What do you think kids of today see in it now? I know a lot of the technological stuff is present in the movie, and that’s something they can relate to, and the story-line having been adapted from Emma (which is turning 200 this December) is a total classic as well, but apart from those factors, what do you think has been part of the magic formula that’s helped this film persist culturally?

Well, you already mentioned a couple of things (like the technology), but I think there’s something about the way that Cher and her friends live their lives in the movie that really doesn’t feel drastically different from how teenagers live their lives today. Obviously the Internet is absent, and that’s a huge thing, but the cellphones, the way she uses her computer like we use fashion apps today, all of that kind of stuff, even on a subconscious level, is something that I think a fourteen or fifteen-year-old sees and thinks, “Okay, I recognize that.” And I think Amy Heckerling did a great job of writing the movie; it’s just one of these movies that is incredibly quotable, and there’s a vibrancy to the language that I think draws people in and still feels very contemporary in a lot of ways.

You also mentioned Emma, and I think that basic narrative arc that’s in Clueless is pretty timeless. But you know (and somebody I interviewed in the book said something to this effect, too), there aren’t as many teen movies that are rooted in everyday behavior; a lot of it is being pulled from YA (like Twilight and The Hunger Games), and the situations are a bit far-removed from what our day-to-day reality might be. And then there are the John Green books, which have inspired movies, but those are usually somewhat unusual circumstances, as opposed to “I like this boy but he doesn’t like me,” or “I got a bad grade and I’m mad at my teacher,” which are things that teenagers actually deal with. Of course, most teenagers don’t have a closet that’s the size of a studio apartment, but I think at its core, Clueless is really recognizable. I feel like there just aren’t very many widespread teenage movies that really capture that, so maybe it’s just because there’s a lack of that kind of material, or a lack of material that’s handled as intelligently as it’s handled in Clueless.

Right. Well, that being said, do you think that this movie would have been able to have been made (and been met with so much success) in any other decade? That period of the nineties was interesting, because it was on the cusp of the digital age, but it still had a foot in sort of “simpler” times, so I do wonder if that unique balance created a window of opportunity that might have been difficult to match at any other time. 

Obviously some of the cultural references would have had to change a little bit, but I think it’s timeless enough that yeah, I think it could have been made a little bit later. A lot of people talk about this movie being a precedent to Mean Girls, perhaps because they’re both Paramount movies and were packaged together in DVD box sets, and I think people now just associate them together, but I do think there are certain things that are similar in terms of quotability and female friendships. (Although Clueless is much, much less cynical than Mean Girls is.) But I think it absolutely could have been made at another time. There are a lot of movies and TV shows that were created in Clueless‘ wake that were telling stories from a female teenager perspective (probably because of Clueless) that suggest that there would have been a market for that.

I agree with you completely, although it just wouldn’t be the same without the amazing cast! Now, you were able to speak with cast in addition to crew, so were there any interviews that stood out to you as being favorites to conduct? (You can be diplomatic here and say “pass”…)

Well, I talked to Amy more than anyone, and I wouldn’t have gone to any of the publishers before I was sure that she was willing to talk to me at length, because if she wasn’t, then there was no book, as far as I was concerned. So I spent the most time talking to her, and she was just great and generous with her time, funny and really smart. Some of the actors (at least in terms of the major stars from the movie) were difficult to get time with, just because they all have their own schedules, and sometimes actors don’t want to talk about something they worked on twenty years ago, but I talked to Donald Faison twice and he was just hilarious, and then I can’t lie, Paul Rudd is the best. [Laughs] It was difficult getting him on the phone because he’s obviously incredibly busy, but he called me on a Saturday of his own accord and said, “Here, let’s talk.” He was really funny and just had really great memories of working on the movie. I also really enjoyed talking to people who maybe weren’t as well-known, like actors who played smaller parts or people who worked behind the scenes, because some of those people had really, really sharp memories of things, and they remembered things that Amy sometimes didn’t even recall. Just being able to pick the brains of so many different people was really, really fun.