Insecure’s Kendrick Sampson on Issa & Nathan, Abolition, and Reimagining Hollywood

For Insecure’s Kendrick Sampson, storytelling is about more than just entertainment; it’s about cultural transformation.

When I hopped onto a Zoom call with the Houston native—who appeared on How To Get Away With Murder and The Vampire Diaries before playing Nathan on Issa Rae’s beloved HBO series—I was immediately mesmerized by his authentic laugh, Southern charm, and heart-melting smile. However, it soon became clear that his passion for real and lasting systematic change burns just as bright as his striking hazel eyes.

As the last season of Insecure unfolds, Sampson speaks with about behind-the-scenes moments, his continued effort to honor the Black Lives Matter movement, and the urgent need to reimagine safety within Hollywood.

What was the culture of filming Insecure like?

Issa [Rae] and Prentice [Penny] set a culture that was generative, supportive, and inclusive of people who normally wouldn’t get these opportunities, even within our communities. The culture was founded in good values. Issa was coming into the industry new, so she didn’t bring a lot of the baggage that the industry can throw at you. She saw it as an advantage instead of an obstacle.

Whatever it was, it was a great recipe for a great culture. It felt like a family reunion. But you know what comes with family reunions, right? I ain’t saying it’s perfect! It wasn’t perfect, but it felt like family. It felt good and supportive.

Everyone who is a part of this show is ride or die. Every single one of them came out during the protests in [the summer of] 2020. The whole cast, crew, producers, everyone was involved in the [Black Lives Matter] movement. They donated, got out the streets, and personally showed me support when I needed it. These people are truly invested in Black futures and our values are common in that sense.

How was it playing Nathan? In what ways are you similar to your character and in what ways are you different?

Nathan and I are similar in that he is from Houston Texas, which is my hometown. He deals with a bipolar diagnosis, which my brother deals with as well. I have a lot of mental health issues that run in my family. So I had the advantage of Nathan having so many conversations I’ve already had!

But, we are different in the way we approach conflict. I am the complete opposite of him. I don’t have much of a filter. When I think things, they come out of my mouth most of the time.

Nathan has a medical diagnosis that impacts the way he reacts to things. It’s overwhelming, and I know a lot of people are like, “Oh, well I get overwhelmed too!” But with bipolar disorder or other mental health issues, it’s a lot more intense and can be physically damaging. Your brain and thoughts can cause your body to react in ways that are unhealthy.

So Nathan has extra trouble and extra hurdles in problem-solving, which totally makes sense. I do not deal with that, so I can’t judge him. I am to the other extreme to a fault, where I’m like, “There’s a conflict? Let’s get through it! Let’s figure it out!” I get excited about figuring out solutions and turning obstacles into advantages. I think that’s really the essence of great communication.

Justin Vaseur

You were very active during the Black Lives Matter protest in 2020. How do you think the movement has impacted the entertainment industry over the past year?

The consciousness of Hollywood has grown exponentially. It was forced to. I am grateful that our nonprofit, BLD PWR, was a big part of that.

At the same time, the power structures are the same. They’re shifting and becoming more conglomerate and capitalistic, and that’s not good for art.

We have a reckoning that needs to be had in Hollywood. We have serious problems with safety on set. Halyna Hutchins died as a result of unsafe conditions. If members of the camera crew can walk out in protest and then hours later one of them is harmed, hurt, or even dies, we have a much, much deeper problem that we really have to assess as an industry. Halyna’s passing tragically highlighted the need to urgently address safety on set.

Set safety goes beyond just physical safety. It includes the culture of transphobia, the culture of anti-Blackness, the culture of misogyny, and even pay equity. All of that is a part of a safety conversation. We need to make sure we’re focused on what true safety is and reimagining safety within Hollywood.

How has your nonprofit, BLD PWR, been helping to reimagine safety in Hollywood?

We put out a letter for Black Hollywood that demands we divest from police. We ultimately want to honor the Black Lives Matter movement, the Movement for Black Lives, and abolitionists from all over the country who were calling for police defunding and abolition.

The thing is, if you remove police from sets, you have to acknowledge that they didn’t really keep us safe in the first place. The only things police are supposed to do on set is keep people from stealing from the trailers, redirect traffic, and so on. Community members can do that! You can hire Black and Brown folks to do that! Because if that can happen internally, that means we have to protect ourselves from the toxic culture we have within Hollywood.

“We need to make sure we’re focused on what true safety is and reimagining safety within Hollywood.”

At BLD PWR we are asking: What keeps Black people safe? What keeps trans people safe? What keeps Indigenous folks safe? What keeps undocumented people safe? Those who are differently-abled, what keeps them safe? It’s about safety from the toxic culture that was birthed in Hollywood and has been perpetuated in a lot of ways. If we start by asking ourselves who are the most marginalized and what do they need, we’ll be in a much better place.

What is your favorite behind-the-scenes moment from filming this season?

There are too many things to choose from! We are complete children when we get together. Especially me and Issa. We’re straight-up children. All I’ll say is that Issa runs very, very fast. If she’s running somewhere, follow her!

My favorite times on set were when a bunch of people were there and we had the music going. We had these pods and masks and everything, but we always found ways to keep each other entertained, even though we had to do it from our little pods.

There is a big Nathan vs. Lawrence debate. Do you think your character deserves to be with Issa?

It really depends on Issa! If she decides that she wants to navigate a relationship with him, I don’t think he’s done something that’s so egregious that she can’t give him another try. Personally, I tend to give people at least two chances. But I’m not a woman in Issa’s shoes so I can’t really make that call for her about if he deserves her or not. I do think they can navigate the relationship in a healthy way, because the best of them is great together.

kendrick sampson lounges on sofa

Justin Vaseur

What projects are you looking forward to working on in the future?

I’m building a production company! I’m excited about working on that. I’m trying to get furniture for this darn house. This is the first time in my adult life I ever owned a TV. I’m working on my career. And I’m working on being the best Kendrick I can be, because let me tell ya, that’s not an easy thing lately!

I’m also excited about the work we are doing at BLD PWR. I’m excited about my next job, whether that be acting, producing, whatever it is. At the end of the day, I love storytelling and I love my people.

This interview has been edited and condensed for clarity.

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