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More Natasha Rothwell, I Beg of You

Insecure’s funniest cast member on tough friendships, comedy, advocating for yourself.

Photo: Rozette Rago
Photo: Rozette Rago

When Natasha Rothwell met Issa Rae over a video call, she was a comedian, actor, producer, theater director with no plans of leaving New York City. By the time Rothwell had gotten to the city, she had already cut her teeth within the improv and sketch scene of Washington, D.C. and Tokyo. She joined the Upright Citizens Brigade, and in 2014 landed a coveted position in the SNL writer’s room. But a chance to be part of the Insecure writer’s room crafting the complicated, 30-something, black characters in L.A. was an offer she couldn’t refuse. “Some people leave New York running and I left a little bit kicking and screaming,” she said. “I have a dog and the whole thing now. So the commitment is real.”

While helping write the character of Kelli — the hilarious, self-possessed, and fiercely loyal friend in the group — Rothwell was asked to bring her comedic skill on camera. Confident in her body and sexuality (and the only character that seems to own up to her own mess) Kelli quickly became a fan favorite. Today, Rothwell is a writer, actor, and supervising producer on Insecure, which is currently airing its fourth season and has been picked up for a fifth, and also an aspiring film and television director. And in her spare time, she’s not afraid to talk politics — whether that means encouraging people to vote or tweeting to remind the president he is “absolute trash.” I recently spoke to Rothwell about working on the show, teaching her team how to advocate for black women, and why she’d rather focus on healing people with comedy rather than punching down at them.

How have you been taking care of yourself during self-isolation?
I’m just taking it one day at a time. I’m an overachiever and a perfectionist, and I think that the pressure to be productive is real. But the reality is, it’s not productivity under normal circumstances. It’s under crippling anxiety and financial uncertainty. Friends, extended family, and relatives might be suffering and so it’s about having grace with yourself and other people when it comes to feeling like you have to do, do, do, and go, go, go.

Is there anything unexpected that you’ve realized or learned during this time?
Prior to all of this, when I would talk about philanthropy I’d always use the phrase, “Do what you can, when you can, if you can.” That’s not just applicable to donating your time and money to charitable organizations, but to yourself. Understanding that you can only do what you can, when you can, if you can.

Some days, I’m writing, organizing, and getting my closet together. And other days it’s just skipping the shower and watching Drag Race and having a cocktail. Both are noble.

I think a lot of people have been forced to be at home with the life that they’ve curated for themselves. I feel really lucky that I love the one that I’ve created. A lot of people, it’s a rude awakening of having to come face to face with all sorts of things.

That actually makes me think about your character Kelli. Insecure hasn’t gotten into her personal life a lot on screen, but she seems more than anyone to love her life. Was that intentional?
Absolutely. I think that Kelli definitely typifies the celebration of making choices that are good for you and not necessarily subscribing to what society might think you should or shouldn’t be doing. It’s about what you want and what makes you happy. And she definitely puts her authentic thoughts and feelings out there without apology. And I think that’s why I love playing her. She’s deeply unapologetic and she loves the life that she lives, where so many of the other characters on the show are seeking and trying to find who they are, and what they want.

Photo: HBO/Kobal/Shutterstock

When tensions started to bubble over with their friend Molly, Issa confided in Kelli about her frustrations. Kelli listened, but didn’t get involved in the drama. A lot of people have trouble doing that in their own lives. 
One of my favorite quotes is, “Friendship is the habitual inclination to promote the good in someone.” And it’s my favorite definition of friendship because it’s the habit, right? You make a habit of promoting the good in someone. And I think Kelli is that kind of friend. Of the women on the show, her focus is not on men. And she doesn’t have this feeling of lack if there’s no man in the picture, and that allows her to be incredibly available to her friends. She’s that Steady Eddie, she’s that rock-solid friend that they can come to her and say anything and she’ll be there no matter how ridiculous.

I think sometimes we confuse promoting the good in our friends with telling them what to do. When sometimes it’s just asking questions that can lead them to answers on their own — and being there regardless of the outcome.

I always feel that people want to know more about Kelli or want to see a bigger story line for her. How do you see your character growing on the show?
It’s interesting because, it’s not just me crafting her in the series and seeing where she fits in. We decide as a collective writer’s room the story we’re wanting to tell overall. The show really is, I believe, a sort of platonic love story. Issa and Molly’s friendship is the spine of our show and the relationship we care about the most. And so I feel like any of the other characters — Kelli, Tiffany, Lawrence — are there to facilitate an understanding of that overall arc. I think of Kelli as seasoning. You don’t want to over-salt your food. I would love to see her continue to be used in a way that can help tell that story, but I wouldn’t want to mess with the recipe.

Kelli wore a Halle Berry B.A.P.S. costume for Halloween, and in the most recent episode, she had on this amazing blue silk suit at the block party. What did you and costume designer Shiona Turini talk about when it came to the vision for Kelli’s style this season?
That suit was one of my favorite outfits of the season. Just that combination of fun, effortlessly sexy, and yet put together and appropriate for the event. It’s something I would want to wear in real life, too. So if you see me in real life rockin’ it, don’t say nothin’.

We’ve had tons of conversations about having Kelli really be as self-possessed in her wardrobe choices as she is in personality, and allowing her to be sexual and have cleavage and show her shape. The relationship between an actor and a costume designer is probably the most intimate on set because they see you at your most vulnerable. Even if it’s something that I wouldn’t wear in my everyday life, once I’m in character, I feel confident and sexy. I feel like I can do my job because I’m not thinking about, “Oh my God does this look okay from that angle?” As a plus-size actor, as a woman of color, that kind of time, care, and attention unfortunately isn’t always given to us.

Photo: HBO

What have you learned about yourself as a black woman navigating this industry?
Early on in my career, there was this feeling that there were not enough roles. And the longer that I’ve been in this industry — and I do think the industry is changing — it’s becoming aware of the overwhelming sense of abundance, that there’s enough for all. With all of these black women who are out here killing it, it’s not a loss for me to see other women of color succeed. And I think that that was sort of the lie fed to me by the industry early on.

You work in front of and behind the camera. Is there an element of the business side you’ve had to adjust to?
I think advocating for yourself, but also really teaching the team that you have around you, on how to advocate for you, especially as a woman of color. That’s a different brand of advocacy.

I think early on in my career I expected that understanding to be inherent. It dawned on me that those were conversations that I needed to have in order to get the best out of my team, and not feel guilty. I’m wired to be like, “Oh, I don’t want to be an imposition.” Which isn’t the case. It’s how can I give them as much information about how I see the world, and how the world sees me, so they can advocate accordingly?

How has the way you grew up prepared you for a career in Hollywood?
I’m an Air Force brat. Each time we relocated it was, in essence, starting over. It really made me be able to connect with people quickly, find my place, and then to do my best not to grieve when I had to leave. There’s a performative aspect to moving to someplace new. You’re always auditioning versions of yourself whether you know it or not.

So many people who do comedy are told at a young age that they were funny. I was definitely not one of the cool kids but I was like, “Oh, being funny is currency.” I was a plus-size black little girl, and a lot of times [in] mostly white environments. I was just like, “Oh, this is a tool and a weapon that I can use to reach people and to bridge the gap.”

I realized very early on the healing quality of laughing and telling jokes. I have two sisters and a brother and so if one of them were upset, I could instantly see the medicinal qualities of comedy in being able to do something to make them laugh.

How does your work as a comedian and your activism tie together?
I think they speak to each other, and I try not to force it. Humor is something that oppressed people have used for a long time to cope. So it’s not surprising that under this current administration you’ll see so many of the folks in the comedy community really using humor to heal and deal.

Right now my biggest concern is engagement in the process — staying informed, not being swayed by Facebook logic or Twitter turmoil. My ancestors died for my right to participate in this process and I feel it’s imperative for others as well. I think apathy is one of the biggest hurdles that millennials, my generation, and future generations will have to get over. This idea that their vote doesn’t count or that the process will go on without [them], and none of that is true.

You’ve mentioned wanting to direct in TV and film. Do you have a dream project?
Well, I started directing proper when I was a high-school teacher in the Bronx for four years. I’ve directed tons of plays, musicals, and one-act shows. As an actor having been directed by hundreds of directors, I’m a student first and foremost. I’m shadowing, studying closely with other directors and visiting sets, and doing all the work to prepare for the opportunity when it comes.

Whether it’s Insecure or watching Pattie Jenkins and Wonder Woman,  watching how these directors work has influenced me a great deal. For me, the types of projects that I’m interested in directing play with gravity and levity at the same time. It’ll have that grounded, emotional ethos,  punctuated with hard moments of comedy. I want to find projects that have something to say, that are additive to the conversation. It’s not a question of if, but when.

This interview has been edited for length and clarity. 

More Natasha Rothwell, I Beg of You