Clueless director Amy Heckerling is still mastering the art of wry, sharp comedy with Amazon's Red Oaks

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Red Oaks, Amazon’s winning, bittersweet nostalgia-comedy set in 1980s New Jersey, finishes its three-season run with a six-episode nest of episodes hatching Oct. 20 on the streaming service. The final stretch makes for a typically good-hearted conclusion to the show, as David (Craig Roberts) faces disappointments after entering the workforce as a production assistant in New York City.

The creative forces behind Red Oaks include executive producer Steven Soderbergh, director David Gordon Green, and creators Greg Jacobs and Joe Gangemi. In addition to Green (who directs the series finale), the show has featured a stable of accomplished filmmakers behind the camera, including the indie movie veterans Hal Hartley and Gregg Araki — and the amazing brain behind Fast Times at Ridgemont High and Clueless, Amy Heckerling.

Heckerling, who is 63 and speaks with a terrific workmanlike mixture of wisdom and world-weariness, chatted with EW about her work on the show. The six episodes that Heckerling directed across three seasons are easily among Red Oaks‘ best — beginning with the perfect, delightful spoof “Body Swap” — and offer audiences great opportunities to see her unique, idiosyncratic eye at work.

ENTERTAINMENT WEEKLY: Did you get positive feedback after you directed the “Body Swap” episode, where Richard Kind and Craig Roberts switched personalities? People who loved that episode felt so happy that you had directed it. 
AMY HECKERLING: That’s really nice. I’m completely surprised. That was such an iconic theme in the ’80s. There was Vice Versa and Like Father, Like Son and 18 Again and Big and also before those, Freaky Friday. It seemed like if the Red Oaks guys were doing a show set in the ’80s, that had to be one of the things that happened. Not that it happened to anyone I know in the ’80s. Not that I know of.

Did you rewatch all those body switch movies?
Oh yeah, all of them. There’s things I love in all of them and there are things that are so lame. But it’s an amazing way to examine your opinion of actors. Some actors you might like more when someone else is playing them. It’s not a comedy, but Face/Off is very much like that. You know they must have had so much fun making it. And it’s so much fun for us. To think, like, “Oh, I love Travolta in this scene. Wait, that’s Nic Cage acting like John Travolta.”

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In Red Oaks, you’ve done other episodes, like season 2’s “The Bris,” which are much quieter and more thoughtful.
I guess since I’m a female, they probably thought I could do more of the romantic, emotional stuff. And then when the boys go on a road trip, it’s directed by somebody else [laughs]. Which I can totally understand. But this last season I got to do more stuff with the guys in the cast. They’re hilarious.

One of your episodes in season 3 concludes with David receiving some very disappointing career news — and then it ends with the classic Peter Gabriel-Kate Bush ballad “Don’t Give Up.”
Yeah, I like that. I can’t really speak to choosing that song, but I think it works really well. There was one place in that episode where David is looking at the clock a lot. Basically, I wanted the music from High Noon, when the whole town is looking at the clock and it builds up all the tension. I wanted to do something humorous based on that. I really thought it was funny but apparently it cost too much.

But speaking of classic movies, I’ve watched this clip of you touring the Criterion Collection headquarters.
Oh, that was tough. They say, “Go talk about movies you love,” and of course you’re not prepared for all they have in there. And in addition to great movies, what they have is fluorescent lighting overhead [laughs].

You pull Fellini’s from the shelf at one point and talk about that for a minute.
? Oh, please. A minute? I could talk about it all day. Listen, I grew up in New York and there was something on TV called the “Million Dollar Movie.” So every night they’d show the same movie, five nights in a row and over the weekend. My parents couldn’t believe I could watch the same movie five nights in a row. Actually, Gilbert Gottfried also did this when he was a kid.

Interestingly, I’ve heard that the one Criterion Collection title that you picked to take home was the Holocaust documentary Shoah.
Yes, that’s true.

And that was because you wanted it for research on something you were working on next?
Yeah. But I’m also highly superstitious because the evil eye will see me and hear me. What I’m working on, I’ll tell you, is not exactly Shoah. But Shoah is a wealth of information.

What other movies really stuck with you when you were a kid watching “Million Dollar Movie” five nights a week?
For me, there was a lot of James Cagney stuff, who I worship. Nowadays you can go to Amazon, Netflix, iTunes, anywhere, and watch a movie over and over. But back then, you were sort of spoonfed what the network had the rights to. And that was my way of learning about filmmaking.

How does your experience working in TV compare to the experience of making films?
Hmm, it’s interesting. The experience is basically the same, but now with streaming, you have the option to binge something or watch it a little bit at a time to see if it grows on you. It’s a very different way to respond to entertainment than it used to be. People used to all go to a movie and see it together and either like it or not like it. And now you have more ownership of what you watch.

Recently I was moderating a panel with the whole cast and crew of Red Oaks and one of the young actresses was talking about the one thing that you possess as a director that a lot of other directors don’t. And you said: “A vagina!”
[Laughs] Well, I didn’t mean to blurt that out. She was saying something like, “Amy has…,” and she was trying to say something really nice about me being a female, but it was kind of an incomplete sentence. So I figured, let’s just go there. Let’s just say it how it is.

You have been so honest and thoughtful about the challenges of women in your industry. And the Harvey Weinstein scandal, once again, makes us realize how unequal the playing field is.
Ugh, it’s horrible. Everybody is expected to chime in with a statement, which I guess I understand. Really, for me, it all comes down to men using their power over vulnerable women. And there’s [abuse] towards kids too. That really sickens me.

But does working on this show put some wind in your sails?
You know, it’s weird to talk about “wind in sails” because, well, what direction is everybody going in? I go to a lot of movies and we all know that a lot of time is spent in the writing and producing of every movie. Then it may or may not ever come out or even be seen on a screen. There’s the Marvel universe, which is wonderful and reliable, but that’s a separate entity. When I talk to my daughter and her friends, they say that everything they like to watch is streaming and they’re watching on their phones.

There was the guy Karl Freund, who was the cinematographer of Metropolis, one of the most gorgeous collections of images ever seen on film. And then a few years later, this same guy was shooting I Love Lucy. And you can say, “Oh my god, great for him, he’s doing classic TV.” But maybe he wasn’t that thrilled to be shooting four people sitting on a couch. The industry evolves for all of us. He couldn’t show these operatic, surrealistic images on I Love Lucy. Things change.

Very true. Though I do think that if major studio executives aren’t throwing money at you to make movies, then that’s really their mistake. Not yours.
That’s very nice to say.

What are you working on now?
Well, I wrote the book for the Clueless musical and we’re starting a lab on that. That’s really been fun because I’m getting involved in a whole new world. And, yeah, what else can I say. It’s nice to learn some new s—t.

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