‘Insecure’ Explores Toxic Masculinity With Kendrick Sampson’s New Character.

Earlier this year Emmy nominee Issa Rae spoke to The Hollywood Reporter about plots and story lines for Insecure season 3. In the interview Issa shared she wanted to explore ‘toxic male black masculinity’ as it relates to black women. “I’m trying to find a way to explore that and get a rounded story line that isn’t preachy” Rae said.

The interview sparked headlines, Issa Rae received a significant amount of backlash and in a follow up interview with NOW THIS Issa clarified she didn’t plan on devoting an entire season to toxic masculinity. She stated the show will focus on adulting and managing everyday issues but from a female perspective. After the interview, show producers and the actors remained hush about the new season.

The show premiered last night and Issa does indeed introduce a new story line about toxic masculinity with a new character played by Kendrick Sampson. The HTGAWM actor’s appearance on the show was a surprise. He attended the Insecure season 3 screening in Los Angeles last month but there wasn’t any press or leaks regarding his having secured a role in the new season.

Kendrick Sampson in Armani at the Insecure HBO screening in Los Angeles.

In the show opener, we learn Issa Rae has a side hustle driving for LYFT. She started the extra job to save money for a new apartment. Sampson plays “Nathan” an attractive but testy LYFT customer who displays passive-aggressive behavior from the time he gets into the car. But even with his bashing of Los Angeles, quickly countered by Issa, there is still chemistry between the two.

Image still of Molly (Yvonne Orji), (Nathan) Kendrick Sampson and Issa (Issa Rae) on Insecure season 3.

The dynamics shift when Issa picks up another male passenger played by Miles Stroter whose unwanted attentions annoy Issa’s friend Molly, who’s along to keep Issa company.

Image still of random LYFT passenger (Miles Stroter) catcalling to Molly on Insecure season 3.
Image still of a random LYFT passenger (Miles Stroter) in the backseat with Nathan (Kendrick Sampson) on Insecure season 3.

Things deteriorate further when the new passenger rolls a cannabis cigarette and begins to smoke without asking permission. Issa is uncomfortable but she confronts the new passenger telling him she would prefer he not smoke in the car. He refuses to stop which prompts Nathan (Sampson) to get involved. His “chivalrous” act escalates quickly into violence and neither Molly nor Issa are able to stop them.


Issa eventually pulls the car over. When it stops Nathan jumps out of the car and runs away leaving Issa and Molly to attend to the remaining (now injured) passenger.

Molly (Yvonne Orji) and Issa (Issa Rae) in an image still on Insecure season 3.

The incident from Issa’s viewpoint is frightening, from her fear of confronting the aggressive male passenger to the violence between the two men. Equally alarming is the resignation the female characters have regarding the incident. Neither Issa or Molly cancel their plans for the evening nor do they talk about the alarming way the situation was handled. This highlights Issa and Molly’s desensitization regarding the violence.

Issa Rae in a still from Insecure season 3.

Later that evening Issa receives a notice from LYFT, Nathan gave her a 5 star rating and a sizable $50 dollar tip.  Whether the generous donation was meant as recompense or something else we are not sure. But we have a feeling we will see more of Kendrick’s character on the show as this story line plays out.

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Nichelle Cole is the founder & editor-in-chief of The Fashion Plate magazine. A respected writer, stylist and influencer, she has been published in fashion magazines around the world.

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