‘Clueless’ Director Amy Heckerling Had To Fight To Keep Females At The Center Of Her ‘Emma’ Adaptation

It’s one thing for a director to helm a generation-defining teen comedy, but Amy Heckerling has the rare distinction of having done it for two separate generations: first with Fast Times at Ridgemont High, and then with Clueless. The latter film celebrates its 25th anniversary this year, an occasion which has led Paramount to deliver a new Blu-ray edition of Clueless, one which can be purchased in a way cool steelbook edition bearing the instantly-recognizable pattern from Cher’s dress in the film. In conjunction with this reissue, writer/director Amy Heckerling hopped on the phone with Decider to discuss the film’s origins, the top-notch character actors in the cast, the lessons she learned from turning Fast Times into a TV series, the disappointment derived from Johnny Dangerously, and her love of Richard Kind.

DECIDER: I have to say that I’ve been a fan since the first time I saw Fast Times at Ridgemont High, but I’m also a huge fan of Clueless.

AMY HECKERLING: Oh, cool, thank you so much!

I know a bit about the origins of Clueless, but what was the impetus for doing the film in the first place?

Well, actually, I had a meeting about a TV idea I had, and then they said that they wanted to do something with the young people that were the cool people, because everybody that came in with pitches about young people was pitching about nerds. And I said, “Well, that’s because they’re all writers.” So I was thinking about what kind of character I wanted to write, and I just started to think about all these optimistic characters and how to incorporate that into a very positive girl, and that became a TV pilot…that they passed on. And then when that company was going belly-up, we got the rights and took it to the studio to expand it into a feature, and I was thinking, “What goes with this optimistic, very positive girl?” And I remembered Emma, and I re-read that. I worked on it for a long time for that studio, until I couldn’t make the notes for what I wanted to say. And then it was in a bidding war. Well, first, everybody in town passed on it. But then Scott Rudin liked it, so everybody liked it.

I read somewhere that, prior to Scott wanting to make it, they wanted you to have fewer female characters.

Yeah, well, they didn’t want to see inside this one girl. They didn’t want to see so much of her. They wanted to see what happens when Josh is by himself, or what’s his family like, or what are the boys doing at school… All this stuff.

So was Scott pretty much fine with letting you do what you wanted to do?

Well, he had notes, but they were pretty much to put it back to where I’d started! It was like we were in perfect sync.

How was the casting process, as far as finding the right up-and-comers? You obviously had a good track record on that front with Fast Times, but you really nailed it again with Clueless, too. 

Well, I mean, looking for young people is like sticking your foot in the river. Every time you do it, it’s a different river. Different people at different times. You can have something in your head, but then it’s just not out there in that moment. But I was fortunate that there were a lot of wonderful people. I didn’t necessarily use all the most amazing actors that were young at that moment in time, but I used the ones that were working for what I want those characters to be. So I was very, very happy with all of them.

I’m always thrilled when Dan Hedaya pops up in the film. He’s one of the most dependable character actors.

He’s so fun! I wanted somebody who felt like he’s a hitman, but he’s your daddy and he loves you, you know? Everybody else is scared of him, but Cher isn’t because, y’know, she doesn’t see things like that.

Wallace Shawn is also great. I talked to him not too long ago, and he still seems amazed by the people who continue to come up to him because of the film.

Oh, that’s nice. I love Wally. He’s one of my favorite people.

Does it surprise you that it’s had such long legs? A lot of teen films tend to fall into a particular era, but barring some of the technology, Clueless holds up extremely well.

Well, the ’90s were certainly a fun time. [Laughs.] But there was a lot of the Jane Austen novel that I was influenced by, and that is completely timeless, as far as the way a young person thinks and the particular character types she’s having fun with, and the romances, the different groups in the social realm… It’s all so perfect in that book.

What was the initial reaction to your decision to borrow from Emma? 

Well, when the script went out to all the studios and everyone said “no” to it ultimately, Amy Pascal called me one night and said, “Did you ever read the book Emma?” She was the only one who figured that out!

After the film’s success, Clueless went on to become a TV series after all. I was curious if you learned anything from the Fast Times TV series that you were able to bring to the Clueless TV series?

Well, the Fast Times TV series didn’t last very long! But it was the first thing I ever did [for TV], and it was a lot of fun, and we had some wonderful people. That was a blast! But there’s something about TV – network television sitcom stuff – that’s not exactly…me. [Laughs.] I was kind of doing what I wanted to be doing, but then I was getting all these notes and trying to make it fit into this mold that wasn’t exactly who I am. So you just do the best you can, and it all moves so fast that you manage to get a few fun things in that you like.

I literally watched every episode – of the few that there were – when it was on the air originally. I loved it. 

Oh, really? Well, thank you! Wow, cool!

And I enjoyed the Clueless TV series, too. It was a nice way of continuing the story. Plus, as you said, you’d wanted to do it as a series in the first place.

Yeah, I didn’t really want to see the sequel of, like, Cher goes to college or whatever. I wanted something where these people could just go on and on doing what they’re doing.

Do you have a favorite project that you’ve worked on over the years that didn’t get the love you thought it deserved?

Oh, well, they say success has many parents and failure is an orphan. [Laughs.] When something doesn’t work, you want to tell everybody what you wanted it to be, and why it wasn’t, and what went wrong… And then you go, “I’ll just shut up.” You know, there’s no point.

Well, for what it’s worth, I worshiped at the altar of Johnny Dangerously when I was a 14-year-old. 

Oh, my God. That is so wild, because I was so depressed when that came out. My ex-boyfriend had a movie come out that day, too. Called Beverly Hills Cop. And his theaters were full, and mine were empty. And I was just so miserable. [Sighs, then becomes instantly upbeat.] But then I had a baby, so I was happy!

Let me assure you that, for a certain generation, the ability to say “iceholes” and then legitimately claim, “No, I didn’t say ‘assholes,'” was invaluable.

[Laughs.] I like that. At first I was, like, “Wait a minute, this is a little corny.” But the writers said, “No, no, no, that’ll work!” Breckin Meyer was a huge fan of it, too. I was, like, “Really?!” [Laughs.] It was just so strange!

Lastly, since I know I have to keep you on schedule, I just wanted to bring up one more series you’ve worked on: Amazon’s Red Oaks. In particular, the body-swap episode, which you directed. The idea of an ’80s trope being used in an episode of an ’80s-set series and then directed by a seminal ’80s director… It was almost too perfect.

Yeah, I liked working with those guys. It was the first time where I was, like, “Okay, I’m on a show, and I didn’t write it, but they’re letting me change things and write things and do stuff.” I felt very happy and comfortable. And, of course, you had Richard Kind and Paul Reiser, wonderful performers, so that’s always fun. And Richard Kind being, like, a college boy, and his son acting like Richard Kind. That’s just a lot of fun, that one. It was, like, “Okay, people will be mad because it’s not like the rest of the show, but…we want to do it!” [Laughs.]

Oh, yeah, it was great. Plus, I’m a huge Richard Kind fan. It’s like shooting fish in a barrel to sell me on watching something he’s in. But he was particularly great in that episode.

He’s so amazing. Anything I see him in… A Serious Man! He’s just amazing.

Will Harris (@NonStopPop) has a longstanding history of doing long-form interviews with random pop culture figures for the A.V. Club, Vulture, and a variety of other outlets, including Variety. He’s currently working on a book with David Zucker, Jim Abrahams, and Jerry Zucker. (And don’t call him Shirley.)

Where to stream Clueless