While the first season of HBO’s Insecure was undoubtedly strong, the second represents an improvement, largely thanks to the palpable ease and chemistry of the show’s central friend group. There’s the messy, honest BFF bond between protagonist Issa (star and cocreator Issa Rae) and Molly (Yvonne Orji)—but this year, that connection is supplemented by Amanda Seales’s Tiffany and Natasha Rothwell’s Kelli, two supporting players newly promoted to series regulars. Thanks to Rothwell’s performance, Kelli in particular practically pops off the screen: She’s the most outspoken and reckless of the group, two qualities that combined in spectacular fashion on Sunday night’s “Hella L.A.” for an, uh, intimate encounter in Hollywood’s iconic Swingers diner. You’ll never hear the phrase “cheat day” the same way again.
Before her role on Insecure, Rothwell made a name for herself as a writer and performer. After graduating UCB’s comedy finishing school and doing a stint in the SNL writers’ room, Rothwell rose to prominence with a standout episode of Netflix’s sketch showcase The Characters. (In it, a segment about subway panhandling turns into an unlikely commentary on spoiler culture.) She was initially brought onto Insecure as a writer before landing her on-screen role, a transition she spoke to The Ringer about—along with dating in L.A., how Trump’s election affected the new season, and how to act your way through getting fingered in public.
I hear you lost your voice earlier in the week, so I’m glad you recovered.
Oh, my goodness. It has been a full nightmare. I went to Whole Foods and lost my mind.
The holistic aisle there is no joke.
I feel like a magician! With my bag, I feel like I can cure anything.
You're both a writer and a performer on the show. How was working on the second season different from starting from scratch?
The really great thing about the writers’ room is that it’s the same as last year. We got one new addition, but the core of who we are, it’s nearly identical. That’s really great to come home to. It doesn’t feel like we’ve changed anything because the recipe’s the same; the fruit’s still delicious. Coming into work has been just incredible, following up with Season 2. Issa and Prentice [Penny] have been really great in creating the climate of the room that we’re not trying to live up to last season—we’re trying to tell great stories. It really maintained that this season, as well. There’s no bar we’re trying to hit or anything like that. We’re just trying to be consistent and tell good stories.
What were some of the stories you wanted to tell?
I feel like, as a single person myself, that it was only natural that once we realized that Issa was gonna be single this season that we explore what that means for a woman, and a woman of color, in L.A. Because L.A. is an interesting land to date in.
I live here. You don’t have to tell me!
[Laughs] So you get it! The city adds an extra specialness to the whole journey, having her explore what it means to go through a breakup. I think that’s the cool thing about this season. So often in our lives, we have friends who go through breakups and we see one side of it. We don’t understand the ramifications of that breakup on both sides. And in the friendship circles! There’s that whole negotiation, like in a divorce: Who’s gonna get Tom? I don’t know! Tom makes a great chili, but he was my friend in college, so I guess I gotta keep him? You have to negotiate who you hang out with and what you do. It’s a cool season to explore all of that.
Along with Amanda Seales, you were promoted to series regular this season on Insecure. How did that conversation go down?
Everything about me being in front of the camera on this show was organic. I was hired as a writer, and my goal was just to be excellent at that. Of course I had very faint dreams of being on the show, but that wasn’t the intent when Issa and Prentice brought me on. About three, maybe four months into the writers’ room, they called me into Issa’s office. I was convinced I was about to be attacked by Nerf guns, ’cause we were in a Nerf war at the time. So you can imagine my surprise when I didn’t get hit in the face by a bullet, but Prentice was just like, “We wanted to make you Kelli. Are you interested?” And I cried. I totally sobbed. Because for me personally, my most complete is when I’m writing and performing. When that synthesis happens, when I can do both at that level, is when I’m most happy. They were incredible at seeing potential and talent and using it.
So when Season 2 came along, it was sort of the same thing, where I wasn’t going in demanding these things or having any expectations. I was just going in with gratitude. I knew I’d be coming back as a writer, and in the writers’ room, I never push Kelli’s agenda, because that feels a little too self-centered in a way that’s not indicative of who I am. I just didn’t know what her fate would be. I got the call that it was going to happen, that I was going to be bumped up to regular … and I cried again. I’m sensing a theme. [Laughs] I get a little weepy when I get good news. I was emotional that they were happy with how I played her and how it was developing, and I could not be more thrilled to get to be her in this season.
Obviously, Kelli made a huge impression last season. What’s it like to play someone that fearless and outgoing?
It’s been incredible. She is not afraid to speak her mind, and she has a mouth, and she’s brave. I feel like, in this political and social climate, that is necessary. Women, we’re answering the call to open our mouths and not stay quiet. And in a more comedic sense, she really does that with her friends. The cool thing about a second season is, in Season 1 we did so much exposition about how they know each other, and where we’re all friends from, and all of that. But in Season 2, we can really explore who they are to each other. And Kelli is fiercely loyal to Issa. I think that’s why she’s mean sometimes about this breakup! She’s a fiercely loyal friend, and it’s so cool to see how that manifests with Tiffany and Lawrence and all the other friends. Which is so different from how I am in real life, so it’s a lot of fun to play.
When she points out to Issa that this guy sat on our couch for two years and abandoned her when she did one thing wrong, I was like: Yes, that is the correct take on this situation.
Absolutely. She’s not afraid to hold a mirror up to Issa, and I think that’s what any good friend does. A really good girlfriend is not afraid to placate you when needed, but also kick you in the ass when needed as well. And Kelli has really good boots. [Laughs]
You referenced the political climate earlier. Did current events figure into discussions about the show going into the new season?
As far as anything social and political in the show, just by virtue of being a show about people of color in south Los Angeles, it’s radical, in this administration, to exist. We don’t have to do much to make it intentional. We’re just being honest and being real and telling the truth about these people, and about people whose stories don’t get told that often. It’s funny that our form of radical protest is existing nowadays. We’re showing that story. We’re not necessarily trying to be a point of conversation, or to be political, but it is what it is, and I think that conversations will be had because of this.
Kelli has a … moment at the end of Episode 4 that's one of the funniest things I've seen all year. What was that like to shoot?
I’m assuming you’re referencing Swingers. That was so much fun to shoot. I’ll speak in generalities: One of the things I love about the show as a fan of the show—I may be on it, I may be writing for it, but I’m a fan of it—I think that it explores sexuality and these women’s sexuality and they don’t hold back. I think it’s really fun to see Kelli get some. [Laughs] It’s gonna be in her own way, on her own terms. I think it’s fun for the audience, too, to see the lines that we cross this season just by being honest. That’s also the titular focus of the show. We say we’re insecure, we say the naughty thing, and the audience feels relief because they identify with it. Like Issa this season, having sex and enjoying herself and being sexually free liberates our audience, too, and cosigns their ability to do what they want with their bodies.
The scene is such a fun piece of comic timing. I don’t think I figured out what was happening until Issa gets the text.
It was very fun to shoot. It’s the most-clothed sex scene that can exist, so I was grateful for that. Kelli’s brave; I am not. But it was still doing that entire scene in this huge room full of people, in complete silence! It was as funny as it could be. I was in great hands. Prentice Penny directed that episode. He’s an amazing showrunner and an amazing director. I felt really safe enjoying my french fries in his presence. [Laughs]
Disclosure: HBO is an initial investor in The Ringer.