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 conversation. I was thrilled — just a few days earlier I had listened to her on a podcast 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, When It Happens to You (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 Twitter profile, 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?