A Day Playing Hooky Changes Issa’s Life Forever on a Classic Insecure

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In a feature spotlighting the best pop culture has to offer, Brian examines how a day playing hooky changed Issa's life on a classic Insecure episode.



Today, we see how a day playing hooky changed Issa’s life on a classic Insecure episode.

This is “All the Best Things,” a spotlight on the best TV episodes, movies, albums, etc.

This is a Year of Great TV Episodes, where every day this year, we’ll take a look at great TV episodes. Note that I’m not talking about “Very Special Episodes” or episodes built around gimmicks, but just “normal” episodes of TV shows that are notable only because of how good they are.

All this month, I’ll be spotlighting great Black-centric TV episodes.

Insecure was a delightful series created by Issa Rae and Larry Wilmore that started Rae as Issa Dee, a young Black woman in her late 20s trying to make her way through life, along with her best friend, Molly Carter (Yvonne Orji), a high-powered lawyer struggling to find her place in the world of law, as well.

When the series began, Issa was in a longterm relationship with her boyfriend, Lawrence (Jay Ellis), but they clearly had lost the spark, and they were broken up by the end of Season 1. Issa’s main job was working for a non-profit helping middle school kids called We Got Ya’ll, with a mostly White staff, and almost all of the staff were extremely dense when it came to racial issues, except for Frieda (Lisa Joyce), the one White colleague who sort of kind of “got it.” In a notable Season 2 storyline, Frieda calls out the behavior of a principal that they were working with who was very supportive to his Black students, but practically abusive towards his Latino students. Issa shuts her down, but in the end, she has to admit that as much as she appreciates how supportive the principal was, she couldn’t put up with his treatment of the Latino students. It was fascinating seeing Issa, who was almost always on the “right” side of all of her work conflicts, be on the “wrong” side for a change.

However, it was also clear that Issa was never really going to be appreciated enough at this job, and that’s why it is so notable in Season 3’s “Fresh-Like” in 2018 to see Issa play hooky for a day, and in the end, realize that she doesn’t WANT to work here anymore, and she quits.

The reason for the hooky is that she runs into a former passenger that she had in her part-time job of being a Lfyt driver, Nathan (Kendrick Sampson), who is new in town. She agrees to show him around the neighborhood, and they clearly have an instant connection, but more importantly, it allowed us to learn more about Issa’s background. In the end, while initially her taking a break was due to wanting to be with this new guy, she realized that she really didn’t miss her job at all, and it was time to move on.

Molly, meanwhile, is having trouble adjusting to the new Black-owned and operated law firm that she is working at, where a lot of the same conflicts she was dealing with at her all-White firm kept popping up here, as well. A big plot point early in the series was Molly agreeing to go the therapy, but we see in this episode that she is keeping things from her therapist, which is never a good sign. Molly had a very two steps forward, two steps back process at her firm in this episode.

Meanwhile, Issa has moved into a new place where she is a building manager, and there is great comedy in her new job. For instance, when she is with Nathan at her place, the daughter of an annoying resident comes to the door, asking for help for her and her mom to get into their apartment. She notes, “I know what you two were doing, you were eating tacos and kissing on the mouth!” (they were). Very funny stuff.

Molly urges Issa to move on, telling her to throw out some of her old stuff, including mixtapes that Lawrence made for her, and in the end, Issa agrees. This was a major step forward for her. This was a sharp script by Dayna Lynne North. Stella Meghie directed it.