Natasha Lyonne: Jenni Konner, as I live and breathe.
Jenni Konner: Hello! I have to tell you that I’m on the sixth episode of your new Netflix show, Russian Doll. I love it so much. We’ll get back to that. But first, do you remember how we met?
NL: I was 16, and I was with my BFF, Jake, who was also 16. Jake was a huge music fan, and I was always tagging along. Your husband at the time was Beck’s tour manager. I distinctly remember us being at the Tibetan Freedom concert, which was put together by the Beastie Boys, probably in, like, 1996. It was the most magical event of my 16 years. Suddenly we were hanging out on Beck’s tour bus. I didn’t really know what to do with myself, in that way that teenagers are just like, “What is a body, why do I have one, and how do I reconcile it with my mind?” And I just remember talking to you and being like, “Yeah, this is my [new] friend Jenni!”
JK: I remember you being one of the most self-possessed people I’d ever met. You’re so well-read, and I remember listening to you years ago on a Marc Maron podcast and being like, “She’s making some references that I don’t even know how to look up. How does she know so many things?” You were mentioning shorts by Fellini, which connects to your show, right?
NL: Yes, the movie you’re referencing is Toby Dammit, starring Terence Stamp. It’s in Italian and part of a  trilogy called Spirits of the Dead, which is based on short stories by Edgar Allan Poe. Russian Doll is influenced by it. There’s something about it that, for me, really encapsulates the way the subconscious experiences a life and how it’s a series of trigger points just coming at you constantly. I love references. I went to NYU briefly for film and philosophy. I dropped out. Instead, I just spent all my time at Film Forum, watching all the movies, and then I would read all the books. It’s the only language I really understood.
JK: OK, so when did you start acting?
NL: I have a SAG card from 1985, and by 1986 I was a series regular on Pee-wee’s Playhouse, which I think of as the greatest job of my career. I don’t think I’ll ever do better work. It’s good to have that handled by the time you’re 6.
JK: What was your first “big girl” role?
NL: I was in Dennis the Menace when I was 12. I played Dennis’s babysitter. That show was exciting because it was with Walter Matthau, Joan Plowright, and Christopher Lloyd. And then, I don’t think he’s too popular anymore, but the big event was being in Woody Allen’s Everyone Says I Love You when I was 16.
JK: Right. That was it. That was the really big one.
NL: I remember becoming very close with [actress] Gaby Hoffmann. We’ve maintained a friendship 25 years later. We had a lot of kind of wild nights; we played sisters with Natalie Portman and Drew Barrymore in that movie. There were so many great people in that film — Goldie Hawn, Tim Roth, Ed Norton. That was definitely the movie where I was like, “This is what I’m going to do for a living.”
JK: Aside from Pee-wee, do you have a favorite experience?
NL: It’s funny. I didn’t really have a high school or college experience, so a lot of my time on set became the formative events of my real life. Slums of Beverly Hills was very familial, and I’m still in touch with all those people. That was very personal for me, playing [the role of Vivian, based on the life of] Tamara Jenkins, who is the writer-director of that movie. I’m still very close with her.
JK: Yeah, I know how that goes. I had similar experiences while working on Girls.
NL: Orange Is the New Black has been huge. The way you have such close working relationships with people for six years of your life and the fact that you see each other through all your human frailties and joys and breakups … I can’t imagine my life without these girls anymore.
JK: That’s such a great way to describe what it’s like to work on a series, actually. You directed the finale of Russian Doll, right?
NL: Yeah, and now I’m also directing the next episode of Orange. Laura Prepon, who has directed a couple of episodes too, came over to my house and spent two hours just walking through the whole process of directing that show, telling me all these special things, tricks to look out for and certain camera angles to get. She was so amazing and generous and loving. It was the exact same with [co-creator] Amy Poehler on Russian Doll. I think if she didn’t believe I could do this thing I’d never done before — creating a show and writing for it and directing some of it — it would have been hard for me to take that leap on my own.
JK: It’s great to have a community. Amy is one of those people who are so good at pushing other people’s voices out.
NL: One incredible thing about recent times is that it really feels like we’ve flipped the script around from women as competitors to our allies in this life. We’ve all decided as a community that this is something we want to get on board with. It’s a huge shift.
JK: Totally. It’s weird because it’s so counterintuitive to what our country is going through. It’s so strange to have that going on at the same time.
NL: Yeah. I mean, that’s sort of the prickly thing for all of us to reconcile.
JK: OK, so I have this great memory of seeing you at Chateau Marmont when you were young and hysterical and amazing. You came downstairs wearing high-waist jeans and a Norma Kamali bathing suit. I remember thinking, “This is the chicest girl I have ever met. She’s wearing a f—ing bathing suit to dinner.” Now the Kardashians do that all the time, but that was in the ’90s. No one was doing that.
NL: I’m going to go out on a limb and say the Kardashians never quite do it with a punk edge. They do many things, but being a little bit punk is not one of them. Chloë Sevigny turned me onto Norma Kamali, as she turns me onto all things. Certainly having Chloë as the one I was looking up to my whole life was really formative. She is the coolest, smartest person in the world. She was into these Norma Kamali bathing suits, so I went to Midtown and bought myself some.
JK: I think our delightful friend and stylist Cristina Ehrlich would be a big fan of that look.
NL: Actually, she would. You and I also share the amazing costume designer Jenn Rogien, who works on Orange and did Girls too. I told her I wanted my character [on Russian Doll], Nadia, to be the perfect blend of Joe Pesci and Marisa Tomei in My Cousin Vinny. She knew what that meant, and that’s what we did. As a result, I would say that’s also become my go-to street-style look, with a little Michael Jackson thrown in, white socks, Gucci loafers.
JK: I love your look in Russian Doll. I don’t know if this is a spoiler, but you really do wear the same outfit a lot.
NL: Obviously, when you see the show, there’s a very specific reason why I’m wearing the same thing so often. But when you think about men in movies, did Jack Nicholson have a lot of changes in One Flew over the Cuckoo’s Nest? There’s something fun about getting into the character’s bones. It’s funny how one outfit can tell so many stories.
JK: You have to manage so much creating a show like this …
NL: It’s a real beast. You’re managing every actor, you’re in the writers’ room, you’re in preproduction, you’re shooting the whole thing — every aspect of every day has a million choices and decisions. The idea that you’re really in your uniform might even be something I got from Orange. I think it’s part of how men get so much done.
JK: No, that’s true.
NL: I love dressing up as much as the next guy when it’s appropriate. If I’m on my way to a Chanel event or going to some party with Chloë, I’ll put an outfit on and I’m over the moon about it. But, for example, when I think back to how many pencil skirts they had to deal with on Ally McBeal, I love the idea of a modern woman on a TV show not having to spend all her energy changing back and forth all day. It gives you a lot more time for all the other things you want to be doing.
JK: This is the perfect way to pivot into the badass question. What makes a badass, Natasha?
NL: In many ways I think of Amy Poehler as my personal touchstone of a badass. I think that probably the biggest misperception of a badass is that they’re a selfish person. There’s something about the word “bad” that implies, like, “mean” or something. More and more what I find to be true of adult life is that it’s so much cooler to be a nice, good person. It really helps you sleep at night. Being honest about where you’re at and not feeling like you need to hide your true self is pretty badass.
JK: I agree, and I am so happy about your life.
NL: Yeah, this hasn’t been an easily won journey, so all that stuff we’ve talked about is very personal to me. Having women who believe in you is not just a platitude. These relationships are the most important thing in my life.
JK: Wait, I just realized that, Jesus, you’re not 40 yet? F— you. What are you looking forward to the most in the next decade?
NL: I guess turning 50, which nobody really leads with. I heard it’s the new 17 [laughs]. Honestly, I’m just confused that I’m not 40 yet. Nora Ephron didn’t even direct her first movie until she was 50. I don’t throw the patriarchy around as much as I should, but I think it’s kind of a false idea that the teen years and the 20s are the best for women. In the 30s, 40s, 50s — that’s when the magic starts happening.
Photographer: Anthony Maule. Styling: Nina Sterghiou. Hair: Tetsuya Yamakata. Makeup: Tina Turnbow. Manicure: Dawn Sterling.
For more stories like this, pick up the February issue of InStyle, available on newsstands, on Amazon, and for digital download Jan 18.