Kendrick Sampson Opens Up About Insecure And Working With Issa Rae - Exclusive Interview

We're just as sad as you are that one of our all time favorites shows, "Insecure," is coming to an end. In its fifth season — which debuted on October 24 — fans will see how the prolific Issa Rae decides to wrap up the storylines of the beautiful characters she wrote that began to feel more like our own friends as the seasons have progressed. But all good things come to an end, and Rae seems to believe that the show has reached its natural ending. "We always planned to tell this story through five seasons, but we couldn't have made it this far without the tremendous support of our audience," Rae revealed to Deadline, adding, "I feel blessed beyond measure to bring our characters' stories to an end, on-screen at least."

In honor of the premiere of the final season of "Insecure," The List had the chance to sit down with Kendrick Sampson, who plays Nathan on the show, for an exclusive interview. He dished on what we can expect from Season 5, what he's been up to, and something that he wishes more people knew about him.

Kendrick Sampson likes to stay busy

How are you doing? What are you up to these days? What are you busy with?

I'm all right. I've had a challenging few days. I'm really tired, to be honest, but [I've] been working on infrastructure-building most of this year. Just hiring folks for the nonprofit BLD PWR and a production company — trying to build up, just trying to build. And, of course, doing my career stuff.

So you're staying busy.

Yeah, yeah. And then, of course, you got family and stuff, and just navigating the world, but yeah. Yeah, I've been definitely staying busy.

Do you give yourself time off? Do you give yourself allocated weekends, or are you a seven-day-a-week worker?

I am working on healthier scheduling, and I'm doing better at taking a couple hours to myself a week to play spades or some s***.

So we're talking about hours, not days at a time, of a break?

No, hasn't gotten to days yet. I'm working on it.

That's good. That's improvement. What do you like to do on your time off usually? Or your hours off?

Eat. I like to eat.

That's it?

To play spades. Rarely, I get to jump on the piano. I [play] piano a lot. But yeah, mostly it's eat, play spades, dance. I like to play music around my house, and I don't go out and dance like that. Definitely not in LA. But I have a great time, even by myself, often dancing around this house.

That's great. That's a really specific skill. I feel like a lot of people wish they could enjoy their company as much as you seem to enjoy yours. So that's excellent.

I do enjoy me.

Are there any projects you're working on that you can tell us about? Anything that's coming up?

Nothing I can tell you about yet.

That's fair. I respect that.

Episode 2 [of "Insecure"] is coming up.

The Insecure star talks about his charity, BLD PWR

I just wanted to say that I loved the letter that you wrote about divesting from the police. I just thought that was really powerful. And I just commend you so much for writing it and for saying what you said. Can you tell us a little bit about your charity, about BLD PWR, and what you envision for the future?

Yeah, of course. BLD PWR was co-founded by Tia Oso, Mike de la Rocha, and myself to bring about strong relationships, ties, and safe spaces to build community with radical organizers, with radical revolutionaries, change makers, [and] academics. And I think we've done a really impressive job with the resources that we've had in doing that. And we're continuing to do so, but this year, we've been focusing a lot, like I said, on the infrastructure-building, just making sure that we can sustain the work long-term, building systems to do that, and trying to do the same thing with the BLD PWR production company. But yeah, it's challenging, and we're still doing the same things, fighting to get those demands realized. As we've seen with ... a lot of the walkouts, and the threat of a strike, we have a lot of work to do in Hollywood to make us safe, and that's a key indicator.

One reason that removing police from sets and divesting from police in Hollywood was our first demand was that it was the only one that is a physical demand that removes something that has to be replaced, which forces people to rethink what safety is. Do these cops actually keep us safe? Well, what about internally? How are we safe internally if a whole camera crew can walk off and protest and still not be heard and still end in fatality or injury? So we have a lot of rethinking to do around safety, and, I think, the way that this industry handles safety and misunderstands safety, which includes ending transphobia and making sure that anti-racism is ingrained in our culture. But we perpetuate that unsafe environment in our stories and in the culture that we export out of Hollywood, through our storytelling. So I can go on and on about it, but essentially, I've been thinking about that a lot lately.

Since the start of BLD PWR, have you noticed a shift in any of the issues that you've been focusing on?

Yeah. We started [at] basically the end of 2018. [That] was when we first got a small grant, our first grant. And since 2018, I think the culture has shifted exponentially, and I think that we've had a huge part in that. And I'm really grateful to be able to say that. With the team that we've worked with and our board members and staff and myself and our partners, led by their work that they've been doing in the community, we've seen a very significant change. And we also see a huge, huge rollback right now on everything we've achieved. I think culturally we've sprung forward exponentially. And I feel like there's a whiplash happening right now because of very strategic efforts to maintain the status quo and white power structures and corporate power structures.

How Kendrick Sampson manages to balance his various different roles

You wear all these different hats as an actor, producer, and just all-around woke individual. How do you shift between those roles that are seemingly contradictory?

Well, one thing I just want to make sure that I clearly convey is that I'm actually saying that we've seen the work, and we're seeing a whiplash in the opposite direction. Right now, we're seeing unprecedented resistance to the achievements, to roll back the achievements that we made. And I mean that with the liberation movement at large, across the world really.

But as far as the seemingly contradictory roles, I don't see them as contradictory. I see them as complimentary. I think just standing for good values in a country that was built on the counter to those values, that was built on the opposite of those values, is always going to be challenging. There's always going to be a lot of resistance. I don't want anybody to mistake that resistance for, "You're not purposed to do these two things at one time." Activism is a lifestyle that everyone should participate in, just fighting for your folks, making sure you leave this world better than you found it. I think our job is liberation. That's what we're supposed to do, our purpose on this earth — no matter what our career is. So the career is always to complement that work. The career is not your purpose. Your passion is not your purpose necessarily. You're passionate about doing those things, but they're tools for liberation, not the opposite. So you have to worry more so about how your work is enhancing liberation, not how your liberation work is hindering your career.

That's an excellent response. Yeah, I guess, regardless of what our careers are, these are still things that we should all be working towards and be aware of and making sure that we're not complacent on a regular basis.

Yep. Yep. Yep.

Kendrick Sampson teases what to expect in Insecure Season 5

So just shifting gears a little bit, I want to talk a little bit about "Insecure." It's definitely on my mind. So the first episode just premiered, which is exciting. Can you tell us a little bit about what we can expect from the upcoming season without giving too much away?

A whole lot of laughs, a lot of plot twists. I don't think they're forced. Sometimes I feel like you get too many plot twists, you're, "I've got whiplash." But there [are] a lot of moments that are organic in people's lives that just happen, that we don't realize how much they change us. And I think it's highlighted in here, but there's a lot of laughs. There's a lot of laughs. A lot of hilarious moments. A lot of drama, as you know. Yeah. I think [a] really special thing in this is you get a glimpse into all of the characters, you get into their lives.

Right. And then how do you feel about it being the final season? Do you feel like it's just the natural end of the series — that it kind of did what it needed to do in the five seasons that it was here? How are you feeling about it?

I totally understand the responsibility to audiences that really invest in these stories and these characters. And still, I think I'm more interested in if Issa [Rae] is pleased, you know what I'm saying? At the end of the day, she made these characters and invested so much, more than anybody else. I know a lot of people who watch think that they invested a whole lot, but she really did. Her life. And so I think if she's pleased, I'm pleased. And I'm just grateful to be a part of such revolutionary storytelling and something that has made such a huge impact on the culture.

Issa Rae and Kendrick Sampson are like 'kids' around each other

Yeah, absolutely. And how have you found it working with Issa? What's that experience been like for you?

She's great, she's great. I think we are children around each other.

So just like you are on the show, yeah?

Yeah, yeah. Just like big-a** kids and can't help it. And that makes it really comfortable and pleasant. She's a pleasant person, just funny, and has a great smile, a great laugh. And she's a good boss, you know what I'm saying? She gives people their due. She makes sure that she lifts people up and gives people that aren't normally given opportunities, opportunities. So I don't know what I could say outside of that.

Had you known her well before the show, or was it really just being on the show that you two became close?

I met her in the audition.


For the show. That was the first I had met her. I've known Yvonne [Orji] for years, actually. We went to church together. I've known Jean Elie for years and a few other people behind the scenes and in front of the scenes. Elle, I've known her from ... she's from Houston. I grew up in Houston. Elle, who plays the neighbor who's always complaining, and she had the kid that was, "Aye, what, y'all doing, eating tacos and kissing on the mouth?" His mama. I've known her for forever. So I knew a lot of people going in. That made it good. And then on top of that, me, Prentice [Penny], and Issa, we share an attorney that's really good people. And then, they just happen to have common values that we all held. So it was a good recipe.

Insecure is unlike any show Kendrick Sampson has worked on before

Yeah. Good combination of people. And have you found that working on "Insecure" has been different than other experiences of working on other shows?

Yeah, yeah. This is the Blackest show I've been on, which is wonderful. The best thing; it's the best. I've been blessed to work with a lot of other Black creatives, but not like this show. I know more Black women directors now than, I think, any other demographic. And Black directors in general. Yeah, it's been a blessing. It's been different. Yeah, for sure. In good ways.

Is it something you can articulate to us as to how working on a show that is predominantly Black talent and Black directors affects you? And what that difference has been like for you?

Yeah, I think it's encapsulated in last year. Being in the show as it's airing its fourth season, and then being in the streets, protesting and organizing, co-organizing protests, and having cast and crew and producers show up at the protests and defend me when I'm harmed, be the first to check up on me and everything, just showed me that I could have a career. That it's possible. Maybe not always supported, but it's possible to have a career and be supported while standing up for the liberation of those who need it most. That is how I see it. It's just, there was something inherent ... I'm not saying every show with mostly Black creatives would take action the same way our project did. I'm not saying that, necessarily, because we're not a monolith. We all have different reactions and s***. But I do believe that it holds a very special place in my heart and definitely gave me a model that I want to replicate and enhance and do better with. Make it even better. See if I can replicate that same culture, as well as deep encouragement that I'm going in the right direction, and I can and will.

Are Kendrick Sampson and his character Nathan similar at all?

In what ways do you think you and Nathan are similar? Or do you not think you're similar at all?

We're similar in that we both like barbecue. We [are] both from Houston. He [doesn't] like guacamole. I'm not down with that. I had a full-on argument with Nathan in my head [about] why he [doesn't] like guacamole, but —

Did you make sense of his reasoning, in your head, as to why he doesn't like guacamole?

Yeah, yeah, yeah, yeah. It's a texture thing. It's a texture thing. I get it, but I don't. Because I got texture things too, but guacamole is guacamole. I know some folks from New Orleans and Houston that don't eat seafood and I'm [like], "How, how? How can you live there?" But anyway, yeah. We're similar in a lot of ways and dissimilar in a lot of ways. The way we handle conflict is very different. I'm very much a head-on type of person. I don't avoid conflict, which is probably ... I'm too the other extreme. So, I got to pull myself back and be, "Is this worth an argument? Is this worth the fight?" So we're a bit different in that, but —

I think I'm very much the same way. When there's something I want to confront, I just do it right then, right there. It doesn't matter what's going on. And I don't know if that's necessarily my best attribute.

Right. Sometimes it is.

Sometimes it's good, yeah.

But I do know him. I do have him in my family and my friends, and I do care a lot about him. And I'm protective over him. And at the same time, when he f***s up, I'm [like], "Yeah, he f***ed up."

That must just be such an interesting dichotomy of wanting to support this character that you are representing. You are the face of Nathan, but he's making decisions that you don't necessarily agree with, but you kind of have to just go with them anyway.

Right, right. Well, you know ...

Yeah. Life of an actor, I guess.

Yeah, I was going to say, that's kind of the cool thing about being an actor, is you get to play out this other person making these life choices. The tricky part is you get to play out these life choices, but then you really hope that the audience gets that the consequences for that character stay in that movie, unless it, in turn, harms people in real life.

Kendrick Sampson believes this is a big misconception about him

Right, right. And then, just for my last question, what's something that you wish people knew about you, or understood about you, a little better?

S***, I don't know. A lot of people are always surprised when I say I play the piano. So that's one thing, I guess. And then, I don't know. A lot of people think that I'm very serious.

And you wouldn't say that about yourself? You wouldn't consider yourself serious?

Not even a little bit. No, I think I actually find humor in everything to a fault, where people have to sometimes be, "I get it, but ... "

"Kendrick, this is serious."

Yeah. Yeah. And I'm [like], "I am taking it seriously, but I just also find this funny."

"Insecure" airs 10 p.m. to 10:30 p.m. ET/PT on HBO. The ensuing episodes will arrive weekly and will also be available to stream on HBO Max, with 10 episodes in total.