In which The A.V. Club finds someone notable to schedule 24 Hours Of media for you to enjoy.

One of the most iconic teen films of the ’80s hit theaters 30 years ago this month: Pretty In Pink, a motion picture that made millions swoon with its lesson that love means never having to dwell on each other’s socioeconomic status while also confirming every romantic sap’s suspicions about the pointlessness of revealing longtime crushes to their cute female friends. Three decades on, the film remains an all-time classic of its genre, and its anniversary is spurring a special theatrical re-release of Pretty In Pink, a digital HD release, and its sudden return to HBO NOW.

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To continue the anniversary celebration, The A.V. Club spoke with Jon Cryer—yes, the Duckman himself—and the film’s director, Howard Deutch. But rather than rehash the same old stories you’ve heard elsewhere (or possibly read in past Random Roles interviews with Cryer, Annie Potts, or Harry Dean Stanton), we asked them to program 24 hours of their favorite teen-centric films not featuring the words “Pretty” or “Pink” in the title. Neither missed a beat in saying “yes,” but when Deutch apologetically admitted having a slight handicap, Cryer happily picked up the slack for his former director.

8 a.m.: Blackboard Jungle (1955)

Howard Deutch: I have to be honest: I was never a big teen-movie guy. [Laughs.] I’m sorry, I know that’s not in line with your article! But I just never was, honestly. Never have been.

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Before I started directing, I worked at United Artists, and I had a company with my partner that made trailers, and we worked on everything from Woody Allen to [Martin] Scorsese to [Francis Ford] Coppola’s Apocalypse Now, so I was involved with a lot of movies that weren’t necessarily “teen movies.” Growing up, I saw many, many movies, but I never was, like, “I’ve gotta see teen films!” [Laughs.] I wasn’t a genre guy. I responded to humanity. To movies that were about something. About people, about behavior. Now, if that was a part of a teen film, then I responded. So because of that, I do have some that I like. One that leaps to mind is Blackboard Jungle.

I was a teenager when I first saw it, and I just liked the non-conformist aspect of it, the rebellious aspect of it. I think John Hughes kind of sprinkled a lot of the values into his films, where you’re responsible for your own life, and to defy authority when you don’t trust it, and all that.

AVC: It shared another aspect with John Hughes’ films: It was one of the first films to utilize rock ’n’ roll in its soundtrack. Hughes has gotten a lot of acknowledgment for the music used in his films. Did you have a hand in compiling the Pretty In Pink soundtrack, or was that him?

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HD: I did, but I have to credit John with introducing me to a lot of the groups, like New Order. He was way ahead of the curve on them. He was brilliant at finding new groups and new music. That was a passion of his, so when he wrote, he would play the music, and we’d listen to new stuff. A lot of the decisions were made mutually, but I have to give him the credit for introducing me to a lot of new stuff. I did choose “Try A Little Tenderness,” though. I’ll take credit for that one. [Laughs.]

9:45 a.m.: American Graffiti (1973)

AVC: Music also played a key part in American Graffiti, as far as setting the time period. But what stood out about that film was that it actually took teens seriously.

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HD: Oh, yeah. I liked American Graffiti. That one and a lot of the movies that I like—and the reason I always responded to John’s writing—had values that were about coming to terms with who you are, finding your identity, finding a sense of worth and value, and discovering if you’re worthy of love. These are the things, the questions that were asked, in that film and in all of John’s films.

AVC: In regards to being worthy of love, the ending of Pretty In Pink was famously changed because the audiences at the test screenings couldn’t accept Andie [Molly Ringwald] ending up with Duckie rather than Blane [Andrew McCarthy]. Were you surprised by that reaction?

HD: Yeah, it was shocking! It was shocking to me and to John, because the whole architecture of the movie was built on that ending, where Duckie’s true love for Andie overcomes all. That’s how it was supposed to end, but teen girls just rejected it. They were, like, “Forget the politics: I want her to get the cute boy!” [Laughs.]

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John was working on several things at the same time, but he took a couple of weeks, and then he came into the editing room one day and sat down on the floor and said to me, “I’ve got it. I know what to do.” And I was relieved to hear that, so we talked about it, and he said, “We’re going to have Blane show up without a date.” And that was it. We shot the new ending in one day—because they gave me one day to shoot it!—and Andrew McCarthy had, like, a crew cut from another film he was doing, so we had to put a wig on him. But we re-tested the film, and it went up something like 25 or 30 points, so… it was the right thing for the movie.

11:40 a.m.: Carrie (1976)

Jon Cryer: Okay, first of all, what year did Carrie come out?

AVC: 1976.

JC: ’76. So I would’ve been 11. So for me, that was my horrifying introduction to what a teenage high school would be like. [Laughs.] And I have to say, it’s interesting, because so many movies from the ’70s and movies that dwell on the ’70s are about the hazing rituals of teen life, because those were all sort of expected. It’s a very interesting change in terms of how my son is going through his high school years and how I went through them. Now those social things, the hazing and the bullying and all that stuff, when I was a kid, those things were just an accepted part of the subculture, but now schools are making a real conscious effort to de-normalize that stuff. So it’s weird! I feel like these kids are going to high school on Mars, you know? Because things are so different from my experience. You sort of go, “Well, maybe it toughened me up.” And maybe it did… or maybe it was just horrible!

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AVC: It’s probably a little from column A and a little from column B.

JC: Yeah, exactly. But I remember Carrie really does set up this world of cruelty and…otherness. [Laughs.] And the absolutely horrifying question is just what kind of a sociopath would come up with that idea. “Hey, let’s figure out a way to humiliate the girl at the prom. Oh, hey, let’s dump a bunch of pigs’ blood on her!” A bucket of pigs’ blood! What… Who… How is that even plausible that you could say, “Oh, sure, somebody would come up with that”? A culture in which that is plausible is very frightening! But we all bought it. We all went, “Oh, sure, that bunch of kids that John Travolta is in, they’re cruel! That’s the kind of casual cruelty that happens in high school!”

AVC: Speaking of Travolta, that’s a film with a cast where you look back and can’t believe all of the actors who either got their start in the film or were helped along the road. There’s also Amy Irving, William Katt, Nancy Allen, and P.J. Soles.

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JC: Oh, absolutely. And supposedly Piper Laurie, who played Carrie’s mom, she felt the thing was a comedy. [Laughs.] She just thought this woman was so outlandish, and she came in and was, like, “I can’t believe you’re going to buy this, but…” And she was doing all this stuff. She just threw up her hands and was, like, “Hey, if you guys think this is scary…”

1:20 p.m.: Fast Times At Ridgemont High (1982)

JC: When that first came out, I was just kind of starting to understand stoner humor, and I remember when the door of the van opened and the smoke came rolling out, I was, like, “I get it now!” I also got that Judge Reinhold was masturbating… and I could not believe that was onscreen! [Laughs.] So that was a special moment for me as well.

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Also, though, I felt like it was a remarkably honest movie. I mean, Jennifer Jason Leigh, she gets an abortion in that! That was a reality in teen life for people that I knew. But people don’t do that in movies now. It was remarkably frank for its time. Oh, and Robert Romanus, who played Damone? I found myself giving Damone’s speech about how to get girls to my son. Almost verbatim! [Laughs.] Because, dammit, he’s right: Wherever you’re at, that’s the place to be.

AVC: He was also right about Cheap Trick.

JC: Yes! Mike Damone was a man before his time.

AVC: Like Carrie, it’s a film that featured a remarkable number of up-and-coming or soon-to-be stars. The closest to a “name” in that film at the time was Ray Walston.

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JC: [Laughs.] That’s absolutely true. But then you’ve got Sean Penn, Eric Stoltz, Jennifer Jason Leigh… Incredible people came out of that. But it was the old generation and the new generation. That was the border, right?

2:55 p.m.: Suburbia (1983)

AVC: This might be seen as a left-field pick, but you actually worked with the film’s director, Penelope Spheeris, a few years later.

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JC: Yes! In fact, the reason I watched it was because I was about to do a movie with Penelope [Dudes]. And it wasn’t meant as a horror movie, but it had that effect on me. [Laughs.] Because, you know, I grew up as a theater kid in New York City, and as bad as New York was then, it wasn’t the urban hellscape that was presented by Suburbia.

You know, one of the things that Penelope did in Suburbia that I thought was really brilliant was cast real outcast kids, real punks, and it made it all… [Hesitates.] Well, I mean, it’s obviously not a documentary—although she’s made that documentary!—but it made the movie so unbelievably fascinating that it was very, very powerful. I recall being very moved by it. And that’s a side of the teenage existence that was like seeing life on another planet for me.

And, you know, with Suburbia, you have to keep in mind that it’s a Roger Corman movie, so it’s got melodramatic parts, and obviously these are non-actors, so there’s stuff that’s not polished at all. But it has a sort of power to it that is kind of undeniable.

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4:30 p.m.: The Breakfast Club (1985)

AVC: Setting aside your own work, do you have a favorite within John Hughes’ teen-film oeuvre?

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HD: Oh, well, I love Sixteen Candles and Ferris Bueller’s Day Off, of course, but The Breakfast Club is one of my favorite films. It’s a masterpiece of behavior, of writing. I just think it’s unique.

6:10 p.m.: River’s Edge (1986)

JC: River’s Edge, of course, has the magic of young Crispin Glover. You had to imagine that the director at one point said, “Yeah, just go nuts!” [Laughs.] Because it’s not a performance. It’s performance art. And a young Keanu Reeves is in that as well! I remember, actually, that a girl who was my roommate for awhile when I first moved to California plays the dead body. So there’s a little trivia for you!

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AVC: Everybody’s got to start somewhere.

JC: Exactly! And her dad was… I think he was the key grip, and a fairly well-known one who worked with on Vilmos Zsigmond on No Small Affair with me. Dicky Deats, that’s his name. But at any rate, that was just an incredibly black vision of being a teenager. My friend Dan Roebuck was in that, and he was playing the guy who kills his girlfriend. Knowing that that Dan is one of the most jovial jokesters I’ve ever met, seeing him playing this brooding hulk was hilarious for me! I’m sure that’s not what [director] Neal Jiminez was going for. [Laughs.] It’s like the opposite of Stand By Me! But it remains a pretty powerful film, and the loss of innocence is really curdled in River’s Edge.

I think it was based a true story. I remember reading a couple of books about disaffected teens having something horrible happen to somebody and just not caring. I think that was not an common trope at that time. But it worked for me, I have to say. Its bleakness did have an effect on me.

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7:50 p.m.: Heathers (1988)

JC: One thing I loved, the thing that was really striking to me, was making fun of teen suicide. How on earth did that movie get made? [Laughs.] But obviously it’s not making fun of the tragedy of teen suicide, it’s making fun of the sociological reaction around it, which is an incredibly brave thing to try and do. And it came up with its own kind of lingo, its own parlance, with things like, “What’s your damage?” It was just great. Again, so many of the movies that I’m talking about are about horrifying teenage hazing and rites of passage that it’ll be interesting to see how my kids experience their teenage years in a time where all of these schools have zero-tolerance policies for these kinds of things.

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AVC: There’s a line in the Wikipedia entry for Heathers that says that “many actors and actresses turned down the project because of its dark subject matter.” Just out of curiosity, are there any films on your schedule that you either turned down or auditioned for but didn’t get?

JC: Hmm. No, interestingly enough. Oh, but another good one that I didn’t mention is The Karate Kid, and that is one that got away. The big ones that got away would probably be The Karate Kid, St. Elmo’s Fire, and… that’s pretty much it, in terms of things that have sort of stood the test of time. There really weren’t that many.

The funny thing about The Karate Kid, though, is that I just thought the thing was so clichéd and dumb… and that’s where I learned that it’s all in the execution. Because [director] John Avildsen, he got fantastic performances, and a kid getting sand kicked in his face at the beach doesn’t come off like a cliché. [Laughs.] I was like, “Are you kidding me? It’s a kid getting sand kicked in his face at the beach! That’s in every comic book!” But it works if you’ve got an actor as good as Ralph Macchio.

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The thing with St. Elmo’s, though, was that I thought, “Oh, my God, these people are so full of themselves!” [Laughs.] And it took their problems just so gravely. But, of course, that’s what it was. It was a soap opera. And that’s one of the things that people like about it.

9:35 p.m.: Say Anything… (1989)

JC: I think it is the best teen romance of the ’80s… and that’s coming from a guy who’s in Pretty In Pink! [Laughs.] It’s just a beautiful, subtle story, great writing, and again Cameron Crowe, who wrote Fast Times. But it’s just full of beautiful, subtle moments, along with some weird ones. Like, her dad’s an embezzler. That was a weird left turn for the plot to take. And yet it all totally works.

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And John Cusack is so memorable as Lloyd Dobler. That was the movie that gave me a real romantic archetype to shoot for: the Lloyd Dobler guy. I was, like, “Oh, yeah: that’s the guy.” That’s the guy I would’ve always liked to be. I never, ever achieved it in my life, just by the way. [Laughs.] That moment never happened.

AVC: God only knows how many guys have tried pulling off the boom box move since then. Even if you’ve never done, there’s always that temptation.

JC: Yeah, we actually did a little nod to it on Two And A Half Men, where mine and Courtney Thorne-Smith’s song was “Mambo #5.” [Laughs.] And we have a fight at one point, and then finally at the end of the show I’m standing outside her window with “Mambo #5” playing. But I’ve dubbed in “a little bit of—LYNDSEY!—in my life,” and it was actually a pretty wonderful moment!

11:20 p.m.: Dazed And Confused (1993)

JC: Yet another rites-of-passage movie where people are just making each other miserable and doing miserable things to each other just because, well, let’s do that because it’s the end of the year! [Laughs.] Why is that… I don’t get why that’s okay. I don’t get why that was ever okay! “This is just what everybody does right now: We do terrible things to each other because we can, and because it’s the end of the year!”

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But what I love is that it doesn’t question that, it just presents it. And it’s full of great acting performances from young people…and not so young Matthew McConaughey! [Laughs.] With his great quote about high school girls: “I get older, they stay the same age!” Again, it’s beautiful, subtle performances. I had not seen Slacker, so that Richard Linklater was a genius was not yet apparent to me. It was Dazed And Confused that showed me the way.

1:05 a.m.: Heavenly Creatures (1994)

AVC: Another dark horse enters the race.

JC: Well, yeah, but what Heavenly Creatures does is convey this maniacal delirium of being a teenage girl in just the most perfect way ever on film. And it’s interesting that it’s a period movie, because the teen idol that they’re going nuts about is Mario Lanza singing “Funiculi Funicula”! [Laughs.] It’s, like, “What?” But it shows that that’s just universal, that it’s just what happens with young women.

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But I think it’s an amazing portrayal of teenage infatuation and just the incredible power of that and the power of teenage fantasies. I mean, most of my life occurred in my fantasies in my teenage years. [Laughs.] You know, if you looked at the outside of it, I was just this kind of pudgy guy, trudging through, going to high school. But inside, all hell was breaking loose! I was saving women from drowning, having crazy adventures, and saving the day. But by looking at me, you wouldn’t know that. Of course, that movie ends with them killing [Pauline’s] mom. Thankfully, my teen years did not end that way.

AVC: You did, however, go on to work with Pauline—Melanie Lynskey—on Two And A Half Men.

JC: Yes! And she was a person transformed. You meet her now, and you can’t believe it’s the same actress!

AVC: It certainly underlines how multifaceted she is as an actress.

JC: Yes, absolutely. And I don’t know if you’ve watched it recently or at all, but it holds up just beautifully. [Kate] Winslet is just…well, she’s great. That’s the thing that made her a star. But also Melanie, she’s the real revelation. If you watch it again, you’ll go, “Oh, my gosh! She’s great!” [Laughs.] She’s funny, she’s incredibly poignant, and just perfect.

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2:55 a.m.: Clueless (1995)

JC: Well, first of all, Clueless was terrifically well-written. It was just clever. And Paul Rudd was in that, for crying out loud! People forget that Paul Rudd was in Clueless. But it was just a perfect light touch, and it was an adaptation that was just perfectly suited, so that it didn’t for a moment appear that it was an adaptation of [Jane Austen’s Emma]. It was just so perfectly of its subject. And Brittany Murphy was so terrific. It’s an amazing cast.

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AVC: It felt like it reinvented the teen film for the ’90s.

JC: Well, it did, because it said, “You can be clever about this. It doesn’t just have to be screwball comedy over super-seriousness. It can be clever.” [Hesitates.] And…that was after Heathers, but it feels like those two were so close at the time.

AVC: Seven years after, actually.

JC: Wow! Well, fair enough: We had to recover from Heathers before we could enjoy Clueless. [Laughs.]

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4:35 a.m.: Rushmore (1998)

JC: Well, Rushmore, of course, is just a great, loopy Wes Anderson movie. What I loved about it was that Jason Schwartzman was a kid with an agenda, you know? [Laughs.] He had a lot of things that he wanted to do. And I really found myself admiring that, because I didn’t really come in contact with somebody like that in my teen years. And I wonder if I would’ve wanted to be his friend or just stand back and let him do his thing. But I thought it was a really tremendous creation.

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I also thought it was interesting because it was a movie about an adult and a child in a sort of competitive situation, which also comes up in Election, actually, but in a different way. Rushmore was a kid trying to get into adulthood and an adult basically having to deal with the challenge of a kid. But the adult is someone who’s completely one that’s completely out of the kid’s league and his domain. I mean, he’s Bill Murray, for Christ’s sake! [Laughs.] But what I liked about it is that it has moments of being a realistic teen movie, but then it’s just so not that, and it actually touches something deeper because of it.

Election, by the way, is another riff on an adult and a child in a very contentious challenge of a relationship. And what’s funny, of course, about Election, is that the adult, instead of trying to foster the child, is actively trying to sabotage them. [Laughs.] Alexander Payne just has such fantastic subtlety in terms of how he portrays relationships with people. That was another movie that took a left turn, where you’re, like, “Okay, I’m on board, but…” That’s great, though, because when you’ve got a director who can take these left turns, it gives you a nice sense of suspense the whole time, because you just don’t know where they’re going to go! They don’t have a formula.

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AVC: Something else interesting about Election is that it presented Matthew Broderick, once the teen, now playing the adult battling the teen.

JC: Yes! This is what happens to Ferris Bueller when he grows up. [Laughs.] And it’s not the Honda commercial, which was always so depressing to me. Because I don’t want to think Ferris Bueller is driving a Honda, you know? He was always a guy who had a sense of personal style! That’s why I always approached people quoting the Duckie thing with a certain amount of trepidation: because I don’t want to let people down. But, like, when James Corden asked me to do it, I thought, “Well, that’s kind of rejoicing in the legacy, as opposed to letting people down. I just hope I can still do it.”

AVC: You pulled it off.

JC: Well, thank you. [Laughs.] Oh, sorry, one last Election moment: I loved when Matthew Broderick was about to have a romantic asignation, and you can see that he’s very meticulous about washing his, uh, junk. I think we’ve all been there. And that’s what America wanted to see: Ferris Bueller meticulously washing his junk.

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6:10 a.m.: 21 Jump Street (2012)

JC: I actually came too prepared, because I was going to include Napoleon Dynamite, which was such a bizarre-world presentation of high school, but also very sweet. I mean, aside from the meat-throwing. [Laughs.] My son loved that movie way before he was near high school age because… there’s something endearing about it. Jon Heder is just such a fantastic oddball.

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But 21 Jump Street just seems like the better one to end on, since it’s more or less about what high school is like now. Also because it’s remarkably more clever a movie than I expected, but just for showing the difference between high school movies when I was a kid and what they’re like now. Just the difference between whether you double-strap your backpack or one-strap it was startling to me. I was, like, “Wait, this isn’t really a thing, is it? People don’t really do this to their backpacks, do they?” No, you’ve got to one-strap it! No matter how painful it is! [Laughs.] No matter how heavy your backpack is, you only use the single strap, so you still look cool!”

I’m sure there’s a reason why. In fact, somewhere–I think found it on Slate–there’s an article where someone tried to trace who the first person was to make double-strapping their knapsack cool for high schoolers. And they did this fairly methodical search of, like, every yearbook in the United States, looking through photos to find out when. Because it is an interesting sociological change from the ’70s/’80s, when I grew up, to the ’90s/’00s. And they found that it was a guy in North Carolina. [Laughs.] He was a tall, good-looking guy, and someone said, “You know, it’s stupid to not use both of these straps!” But he said, “But that’s how it’s comfortable!” And then the rest is history.

AVC: We’ve come so far since Carrie.

JC: [Laughs.] We have. We really have.

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