Monica Lewinsky

We met back in 1999 through a mutual friend who just happened to be the inspiration for one of the most iconic characters of the 80s, Ducky from Pretty in Pink. You may know her from her other work too, The Breakfast Club, Sixteen Candles, or more recently, Ryan Murphy's feud, Capote versus the Swans.

And while I've known Molly for 25 years, I had never actually talked to her about being catapulted into fame at such a young age. And so as someone who became well-known overnight unintentionally, I was interested to talk to Molly about how she navigated becoming a superstar after acting in a string of coming-of-age films.

And while I've known Molly for 25 years, I had never actually talked to her about being catapulted into fame at such a young age. And so as someone who became well-known overnight unintentionally, I was interested to talk to Molly about how she navigated becoming a superstar after acting in a string of coming-of-age films.

Anyway, I hope you find something to connect to in our conversation, and thanks for joining us on Reclaiming. Thank you to our presenting sponsor, Audible. Visit audible.com slash reclaiming to find your next listen. Thank you to our sponsor, Reformation. Visit reformation.com to see why they're my go-to for stylish and sustainable fashion. Thank you so much for doing this. Welcome to Reclining.

Anyway, I hope you find something to connect to in our conversation, and thanks for joining us on Reclaiming. Thank you to our presenting sponsor, Audible. Visit audible.com slash reclaiming to find your next listen. Thank you to our sponsor, Reformation. Visit reformation.com to see why they're my go-to for stylish and sustainable fashion. Thank you so much for doing this. Welcome to Reclining.

Thank you. So happy to be here. Aw, thanks, Molly. It's funny because I was thinking about how on the way over that we were doing this in New York and how if we were in L.A., I would have worn my Molly shoes. Because I don't think you know that every time I see you, I like copy some outfit thing that you have some aspect.

Thank you. So happy to be here. Aw, thanks, Molly. It's funny because I was thinking about how on the way over that we were doing this in New York and how if we were in L.A., I would have worn my Molly shoes. Because I don't think you know that every time I see you, I like copy some outfit thing that you have some aspect.

And I bought these red heeled espadrilles a few years ago because I remembered you wearing heeled espadrilles with jeans and a cute top somewhere. And I was like, that's so cute. It looks so cute. And I've only worn the shoes once.

And I bought these red heeled espadrilles a few years ago because I remembered you wearing heeled espadrilles with jeans and a cute top somewhere. And I was like, that's so cute. It looks so cute. And I've only worn the shoes once.

Were they not comfortable? No. No, they are. You know those items that you put them on and you're like, yeah, not today. Yeah.

Were they not comfortable? No. No, they are. You know those items that you put them on and you're like, yeah, not today. Yeah.

Yeah. Especially that I find that happens a lot with vintage pieces. And I know you have a lot of vintage stuff. So, you know, I didn't know it at the time, but it turns out that when I was five, I saw you in Annie. No way. It was... like seared in my mind because it was actually the first time I went to a proper theater to see a musical or play. Who took you? My mom, my mom.

Yeah. Especially that I find that happens a lot with vintage pieces. And I know you have a lot of vintage stuff. So, you know, I didn't know it at the time, but it turns out that when I was five, I saw you in Annie. No way. It was... like seared in my mind because it was actually the first time I went to a proper theater to see a musical or play. Who took you? My mom, my mom.

And so my dad took me to see the movie version, which were you also in the movie? I was not. Okay. So I had already aged out by then.

And so my dad took me to see the movie version, which were you also in the movie? I was not. Okay. So I had already aged out by then.

Aged out of like being a young person. And so it was, you know, it was interesting because that was seared in my mind. And then a few years later, I remembered, you know, seeing you on Facts of Life. And then when Sixteen Candles came out, it was, oh, it's the girl from Facts of Life, which, and I know you weren't always on.

Aged out of like being a young person. And so it was, you know, it was interesting because that was seared in my mind. And then a few years later, I remembered, you know, seeing you on Facts of Life. And then when Sixteen Candles came out, it was, oh, it's the girl from Facts of Life, which, and I know you weren't always on.

But you had such a presence and you had it from such a young age and sort of I felt like you brought this sense of depth. Like you just exemplified someone who is a layered person and had a lot of depth. And so I made that connection. And then, of course, watched all the John Hughes films six bajillion times. So in many ways, yeah. I felt kind of like I grew up with you.

But you had such a presence and you had it from such a young age and sort of I felt like you brought this sense of depth. Like you just exemplified someone who is a layered person and had a lot of depth. And so I made that connection. And then, of course, watched all the John Hughes films six bajillion times. So in many ways, yeah. I felt kind of like I grew up with you.

Yeah.