I met Molly Ringwald on the radio. I mean we were literally on the radio together. In March of last year she was guest-hosting a public-radio show and invited me to come in for a (1). I was thrilled — just a few days earlier I had listened to her on a (2) and found her funny, smart, and blindingly self-aware. I suspected we shared similar viewpoints about the complicated and personal concept of “ambition,” especially because we are both women who want to break out of our assigned roles of “artist” and “actress.” The on-air conversation flew by, and we have continued it since, reading each other’s books, watching each other’s movies, and forging a friendship over dinners and email.
What I’ve learned about Molly is that she’s extremely comfortable in her own skin. Her probing intellect is not at all at odds with her love of pretty things, whiskey sours, and ordering the most embarrassing things on the menu without excuses. She is candid, curious, and gently but firmly opinionated.
If you are an American woman, you know Molly from her iconic Teenage Three: *Sixteen Candles* (1984), *The Breakfast Club* (1985)*,* and *Pretty in Pink* (1986). These three films resulted in full-blown movie stardom and made her into the somewhat reluctant avatar of a generation at the tender age of 16. But rather than let this initial fame define her, Molly took a Hollywood detour and made creative career choices. Here are just a few things you might not know about her: She made a film entirely in French. She has had an eclectic stage career including Broadway musicals and more intimate productions — in 1999, I saw her brilliant, chilling performance as Li’l Bit in Paula Vogel’s Pulitzer Prize–winning play *How I Learned to Drive.* She tours the world performing rich and seasoned interpretations of the American songbook with a jazz band and is about to release her second CD. She is the author of three books, including her first novel, * (3)* (2015), a series of astutely visceral portraits of relationships stretched to their limits.
Molly lives just outside New York City with her husband and three children. The last time we had dinner we discussed embracing imperfection and trying to do too much while messing up a lot. We consider ourselves anti-superwomen. We ate too much (and maybe drank a little too much) and she almost missed her train, sprinting barefoot across Grand Central Station with her platforms in her hand, then jumping aboard as the doors closed behind her. In that particular instance, she told me, she *did* feel like a superwoman.
When it came time to chat for Lenny, Molly and I sat down in my studio with a plate of chocolate-covered graham crackers and my recording device, once again unsure of exactly where our conversation would go.
**Laurie Simmons:** In your (4), you describe yourself as “actress, writer, singer, mother, your former teenage crush,” which is hilariously self-aware. Were you conscious back in the ’80s and ’90s of being everyone’s teenage crush?
**Molly Ringwald:** It did feel like the world had a crush on me. Which was a nice feeling. But then if you have any lucidity, or if you are prone to anxiety, which I think I have been my whole life, you always have the feeling that it’s going to change, that it’s ephemeral and it’s not going to last.
**LS:** You felt that you had everyone’s approval, but that they might suddenly disapprove of you?
**MR:** Yeah. Because that had actually happened. After my first movie I showed up two months late to seventh grade, and all of my friends had abandoned me. I had no friends at all, which was very, very painful. I felt completely isolated.
**LS:** That is such a classic seventh-grade move.
**MR:** Yes, classic. And boys were always too shy to come up to me. If I wanted to go out with anyone, I always had to make the first move. I don’t think, in my entire life, anyone has ever made the first move.
**LS:** That’s true for me too. In a way it was a good thing because I realized I might have to ask for the things that I wanted in my life. What is your perspective on those teen years now?
**MR:** I feel a lot of tenderness for myself. Because I beat myself up on a regular basis, and still do, for not accomplishing everything that I feel like I should have accomplished, or still want to accomplish. I have that critic in my head.
**LS:** I think people reading this will be surprised to think you don’t feel accomplished, now or then. By age 16 you had made three iconic movies.
**MR:** Those movies were not exactly what I had planned for my career. I thought that I was going to do much more conventionally serious work.
**LS:** It’s almost comical to imagine a teenager deciding she will do conventionally serious work. And *Sixteen Candles,* *The Breakfast Club,* and *Pretty in Pink* did have a very serious impact. People feel like they grew up with you.
**MR:** Those movies were so important to the people who watched them. I think they offered a different way to be a teenager — how to not feel so bad about feeling like an outsider and how to get by when you feel different from everyone else. They showed that everyone kind of feels that way. It’s a comforting thought.
**LS:** Do you think that’s how John Hughes — who wrote all three of those films and directed two of them — felt? Was he reliving his teen life through these movies?
**MR:** He wrote a lot from personal experience. John had a little PTSD about his time in high school. He was really, really sensitive.
**LS:** In my own work I try to focus on where I am in my life in the moment. The idea that a grown man would presume to understand the teenage experience almost makes me think that he had a sort of arrested development, not in a negative way, but an artistic arrested development.
**MR** **:** When I first started working with him, he was 36, eighteen years older than me to the day. We share the same birthday. He was very present and really related to us . He obviously had communications with older people, but I really felt like he was most comfortable talking to us.
**LS:** Did he ever express the desire to make similar movies with adult characters?
**MR:** I always expected him to write the same kind of movie for adults that he was able to write for kids. He never did. Once he finished with the teen movies that I was in, he went in such a broad direction. He did *Home Alone,* these slapstick films.
**LS:** And yet, *Home Alone,* as broad as it is, is about the fright of being left behind, which deeply connects to the whole teenage experience. You feel perpetually home alone when you’re a teenager, which is why you try to turn your friends into your family.
**MR:** I think John really did feel isolated and alone, although he had a wife and kids and a nice life. After a while he became a raging Republican. He’d always had a conservative streak, in addition to this sort of rebellious, subversive attitude. But no one else has ever managed to make anything for teenagers that has the authority of his work, or been able to capture the Zeitgeist in that way again.
**LS:** Not long after those movies, you left Hollywood — the city and the industry — and moved to Paris. You’ve always chosen a very personal path.
**MR:** I might have been able to extend that period of time and done more big blockbustery movies, but I don’t know if I would have been as interesting a person. My mom told me as a child that I had a very low tolerance for boredom. I wasn’t satisfied with what most kids seem to be satisfied with. I would take my bed and move it. I would put my bed inside the closet.
**LS:** I totally relate to this. I slept in the bathtub for a while, or on the floor. You are trying to reinvent your comfortable, prescribed surroundings. You are trying to shake things up.
**MR:** Yeah, because everything looks different. When I was in my bed in the usual spot I looked at everything one way, but then when I was facing another direction and it wasn’t familiar it was a little scary. I was trying out all of these things.
**LS:** What about this drive to push yourself out of your comfort zone to try all of these new things? You’re an actress, a singer, you’ve written three books, and you’ve written for *Vogue, Allure,* and *The New York Times,* among others. Why so many different hats?
**MR:** I think they all satisfy different parts of my brain. I just do what I love. I enjoy acting, but only if I’m interested in the material. I sang jazz as a child, and I wanted the experience of singing and hearing my adult voice rather than my child’s voice, and to perform with someone other than my father, whom I love. That’s now grown into my recording and performing music professionally.
Writing is also something that I’ve done for years and wanted to put out there. My husband is a very fine editor and writer, and I made him promise to be honest. I told him, “This is not the moment for you to say ‘Hey, you look great in those jeans’ if I don’t. Just tell me and be brutal.” He was very kind, but also critical of things he thought needed to be clarified.
**LS:** Your novel, *When It Happens to You,* has a persistent theme of betrayal. What does betrayal mean to you?
**MR:** Betrayal is something everybody has been through in some way. Within the book, there are multiple stories, and every story deals with some type of betrayal: there’s marital betrayal, a mother betrays a daughter, a man betrays himself artistically.
It’s incredibly visceral. I remember, at one point, I was struggling so much that my husband and my therapist both said, “Just don’t write it if it’s that upsetting.” I said, “I have to.”
I felt I had to understand everybody’s place, everyone’s accountability, and also where everyone could go from there. To recover and come through betrayal, you need forgiveness. That takes a real choice. It doesn’t just happen. It’s the thing that elevates us as human beings. Betrayal and forgiveness were the two themes that I was obsessed with.
**LS:** After we’d become friends, you wrote me the sweetest email saying, without embarrassment, that you feel we seek people in our lives to fill a space, and I fit into a Laurie-sized space that had been waiting there, empty. I was so flattered and touched and also impressed that you were comfortable talking about an unfolding relationship. What are your thoughts on friendship? Do you prioritize friendship with women?
**MR:** Female friendship is incredibly important. In raising my daughter Matilda, we were told that playdates are more important than you realize. Connection is a skill that’s taught, and girls really need to learn to trust women, to know that their women friends will have their back, and that you can talk to your female friends about things you can’t talk to anyone else about. I think that’s something that begins in childhood, and it’s something I lost at a certain point. I don’t feel like I’ve made friends incredibly easily, and I haven’t had a lot of mentors. Female mentors.
**LS:** I also felt I had no female mentors in my life until very recently.
**MR:** I’ve been looking to women who are a little older than me who have more experience, but who I can connect with. Those are the people that are the most interesting to me. I suppose that is what made me want to interview you on the radio. I’ve realized that once you define what it is that’s important to you, in some way it appears. That’s always been my experience in life.
*This interview has been condensed and edited.*
* (5)* *is an internationally recognized artist, known since the 1970s for her staged photographic works. Her work is included in the collections of the Brooklyn Museum, the Museum of Modern Art, the Guggenheim Museum, and the Whitney Museum, among others. Recent solo exhibitions include the Jewish Museum, New York and the Contemporary Art Museum, St. Louis in 2015. Retrospectives of Simmons’s work have been held at the Gothenburg Museum of Art in Sweden in 2012 and at the Neues Museum Nürnberg in Germany in 2014, and another will take place at the Modern Art Museum of Fort Worth in 2018. Simmons has just completed production on her first feature film, titled* My Art.