Natasha Rothwell on Saying Farewell to Insecure and Whale Watching With Jennifer Coolidge

Natasha Rothwell headshot
Courtesy of Rozette Rago

On Insecure, the fabulous foursome at the center of the show’s drama have always stirred up the laughs. That is largely thanks to Kelli Prenny, the group’s bold, charming, and confident friend. Though she may not always be at the center of the drama, Natasha Rothwell, who plays Kelli on screen, has turned the character into a fan favorite, making her the embodiment of growth on the series. In the fifth and final season of Issa Rae’s beloved HBO series, Kelli goes to her college reunion at Stanford only to be presumed dead by her classmates; quits drinking in an attempt to find enlightenment; and has, surprisingly, pivoted to full auntie mode with Tiffany’s (Amanda Seales) young daughter. Rothwell, who has written and produced the series for many seasons in addition to starring on it, also directed an episode of this season (and wrote a standout one in season four) in which Issa’s romantic relationship with Nathan might be on the rocks for the last time.

Calling from London, where she is currently filming Wonka with Timothée Chalamet starring as the titular confectioner, Rothwell opens up about Kelli’s arc in the final season of Insecure, whale watching with Jennifer Coolidge while filming The White Lotus, and the one musician that can make her giddy as a schoolgirl.

You’ve been there since the beginning—what’s it like for Insecure to truly come to an end for you?

I’m very much in denial. [Laughs.] The show is everything to me. It, in no uncertain terms, changed my life for the better. People always look at us on Instagram and say, “Do you guys really love each other?” And it’s like, yes, we do! I talked to Jay [Ellis] yesterday. For me, it’s not just saying goodbye to Kelli, who has also changed my life, but it’s saying goodbye to the family that met me, helped raise me, and gave me opportunities. I’m not ready to say goodbye, but what gives me peace is that I have them in my life for forever.

Kelli has always been hilarious, but setting her up this season to have an existential crisis from the jump was next level. You’ve been a writer on the show in addition to acting on it, but did you always know where Kelli would go as a character?

From the beginning, one of the things I loved about Kelli as a character is that she’s consistent. She’s not trying to be something else. She’s not apologetic about who she is or what she plans to do. She loves herself, she loves her job. She loves men! She loves her body. She’s the glue, trying to make sure her group stays together. To have the premiere this season be a moment where she is forced to really be thoughtful about who she is and what she wants to leave as a legacy is such a cool opportunity to show more colors on Kelli, and an introspection that we don’t necessarily get to see. Over the course of the series, she does have moments that are more grounding. She’s capable of being hurt, she wants to be there for her friends. She has a lot of colors that keep her from being a caricature.

It’s also so fun watching Kelli transform into the fun aunt for Tiffany’s daughter, Simone.

In season four, she says some things that would suggest she isn’t going to click with Simone. But this little baby is now her BFF and she’s really leaning into being the auntie, in a very fabulous fit by Shiona Turini. Had me on my best Janelle Monáe! I was very excited for folks to see that look.

You directed episode six, which ends with Nathan and Issa seemingly at an impasse. You also wrote the episode from season four in which Issa and Lawrence start to rekindle things. What is going on with Issa’s romantic life?

When I pitched episode 408 last season, I was like, let’s do a capsule episode where we see them good. At the end of the day, my heart beats in rom com. Their journey has feelings of an anti-rom com, rom com. The episode I directed in season five, the core of it is about owning your choices. Nathan owning his choices to be a part of this barber shop, Issa owning her choice with Crenshawn. We see Issa really try to come to terms with that. For me, it wasn’t necessarily her inability to see things from Nathan’s perspective, it was her realizing, here’s this guy who she loves and wants to be in a relationship with and wants it to work, but wanting something and needing something are different! And she’s realizing her needs aren’t being met. The devastation you see is her realizing he doesn’t have the capacity to give her what she needs. Issa before would’ve tried to make it work even though it wasn’t, and it would’ve been inauthentic in that she’s not honoring her wants and needs. But she’s growing and part of that growth is making decisions and finding your own way, and not feeling like you have to cash the check that society wrote.

I was rooting for Nathan and Issa! Are you team Nathan or team Lawrence?

As a fan of the show, I will always be team Lawrence.

Your performance on The White Lotus was praised by critics earlier this year, too. What’s the most memorable part of being in that very acclaimed project?

We shot during the pandemic, pre-vaccination. Prior to that, it was just me and my dog for five months, alone. I hadn’t seen another person and it was just incredible to arrive on set and be around other humans and socialize! We supported each other through the election. It was a very bizarre time. Just being there was a positive memory. One of my favorite scenes: Jen [Coolidge] and I are on the boat and she’s trying to beckon Jake Lacy’s character over. This didn’t make it into the show, but we were out in the ocean and a whale did a cartoon-style jump. I ruined the take because I lost my shit! I was like, we are in nature! The crew grabbed their cameras and everybody turned into a kid. Then another one crescent jumped! They were all doing that. It was crazy to be in open water, shooting the show that none of us knew would have this response. But boy, am I grateful!

The White Lotus. Courtesy of HBO.

Let’s get into these Culture Diet questions. What’s the first thing you read in the morning?

The New York Times. I listen to The Daily, but if I can’t listen to that, I just read the bullet point headlines from the day. I go on Twitter to see what’s trending so I can be aware of what’s going on in real time. Then, I’m on Instagram, I’m scrolling through TikTok, I’m watching TV.

What’s the last thing you Googled on your phone?

“How to ship coffee to the U.K.” There’s a specific brand, an iced coffee situation. A lot of my searches are “can this come here?” I’ll be here until the end of January, so I need my stuff. I’ve been making do.

Besides Insecure, what other shows have been keeping you up at night?

I loved Sex Education on Netflix. I watched Starstruck on HBO Max—it was so good! Ted Lasso. I’ve been watching so much. Inside Job—I do a ton of animation and voiceovers, so I watched that on Netflix. There’s a documentary about homes on Apple TV+, and I love all things architecture and design. And there’s a category I call “my murder shows.” Any documentary about a crime, I’ve probably seen it or it’s on while I’m writing.

What’s the last movie you saw in theaters?

The premiere of Sonic the Hedgehog. February 2020, I did the big red carpet and it was in a theater and that was the last time. I’ve seen a ton of video on demand. I cut my teeth in New York, so there were days I would choose between a slice or a movie. I was broke! I would just go to the movies by myself. If it was one of those awful hot days in the summer, I would pop into a theater. That’s been one of the biggest devastations when we talk about the movie industry.

What’s the last song you had on repeat?

It was a song on Insecure. “Sunbathe” by Tainy and Miguel. It’s a bop. I tweeted this before, but I want there to be a jukebox musical of all of Miguel’s music. I would go see that. I was schoolgirl-giddy nervous when I met him because he’s such a talent. I never assume people watch the show or know who I am, so I introduced myself and he knocked my hands away and gave me a hug. My spirit left my body!

What’s the last concert you went to?

Lizzo! October 18, 2019. On my birthday. It was church. It was a religious experience!

You mentioned being really into design. What’s the last piece of art you ogled or bought?

The last purchase was a reprint from Ronald Jackson, an incredible Black artist. He does paintings of Black individuals that have colorful floral masks on, and it’s an interesting study in the masks that we wear and how we are perceived [in life]. Frieze London in Hyde Park was happening when I got here and wasn’t shooting yet, and it was awesome to see.

You are a Libra, but are you into astrology at all? Do you feel like it’s accurate?

I think it does match up with me in a way that creeps me out. I’m very much a cynic, but when I moved to Los Angeles it was like hiking and astrology were mandatory. You need to know your sign, so you get your birth chart done, and then a bitch got crystals. There is a slippery slope into that world! [Laughs.] I take what helps and leave the rest.

What’s the last thing you do before you go to bed?

I usually listen to music or an audiobook. I’m not going to lie, I wish I could say I turn off all my screens and meditate. But I’m very much addicted to my screens. I’m reading The Vanishing Half right now and it’s been my favorite thing to put on audiobooks and walk around London. My first month was Brené Brown’s Workbook for the Gifts of Imperfection, so I’m very much coming into my own here.